Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University...
Transcript of Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University...
![Page 2: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/2.jpg)
![Page 3: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/3.jpg)
www.chem.uiuc.edu
![Page 4: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/4.jpg)
![Page 5: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/5.jpg)
User Name: netIDPassword: netIDNo - in netID
![Page 6: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/6.jpg)
Change your password!
![Page 7: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/7.jpg)
ChemNet
Requires Microsoft Internet Explorer
![Page 8: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/8.jpg)
2 points/lesson
Due May 2, 2001
![Page 9: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/9.jpg)
Laboratory NotebookReference
Data
Observations
Properties:
compoundssolvents
![Page 10: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/10.jpg)
Laboratory Reports
![Page 11: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/11.jpg)
Safety EquipmentEye wash faucets
Eye wash bottles
Overhead showers
Fire blanket
Fire extinguishers
Fire-emergency alarm box
First-aid box
Exits
![Page 12: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/12.jpg)
Room 467 Noyes Lab
Mark location of safety equipment on map of room.
![Page 13: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/13.jpg)
Contact your TA immediately
![Page 14: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/14.jpg)
GradesLaboratory Reports
2 50 minute Exams
On-line Quizzes
ChemNet
15% A 30% B 50% C 5% D + E
230
2x100 = 200
10*10 = 100
16*2 = 36
![Page 15: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/15.jpg)
Hour Exam Dates
Exam 1: Thursday, March 1, 2001
Exam 2: Wednesday, April 25, 2001
Dates:
Time: 7:00 p.m.
![Page 16: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/16.jpg)
Breakage Replacement Card
![Page 17: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/17.jpg)
Change Section - Makeup Labs
Mike Eubanks469 Noyes Lab
![Page 18: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/18.jpg)
Melting Points and Mixed Melting PointsExperiment 1: Identify a compound by its meltingpoint and mixed melting points.
Acetamide
p-Aminobenzoic acid
Camphoric Acid
trans-Cinnamic Acid
Malonic Acid
p-Nitrophenol
Resorcinol
Succinic Acid
Urea
113 - 115 oC
188 - 189 oC
183 - 186 oC
133 - 134 oC
135 - 137 oC
113 - 115 oC
110 - 113 oC
187 - 189 oC
133 - 135 oC
![Page 19: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/19.jpg)
A sample is putin the bottom ofa melting pointtube.
![Page 20: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/20.jpg)
Put a small amount of the compound in theopen end of the melting point tube.
Turn over and tape the closed end on the desktop until the compound falls to the bottom.
![Page 21: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/21.jpg)
Sample in themelting pointtube.
![Page 22: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/22.jpg)
Use a Thiele tube filled withmineral oil to heat your sample.
![Page 23: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/23.jpg)
Attach the melting point tubeto a thermometer.
![Page 24: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/24.jpg)
Heat about 5o per minuteuntil within about 10o ofthe melting point
Near the melting pointheat at 1 - 2o perminute
![Page 25: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/25.jpg)
Mel-Temp in the lab
![Page 26: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/26.jpg)
Temperature
Starts to melt Finished melting
m.p. = Start - Finish
![Page 27: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/27.jpg)
Why is salt put on snow covered roads?
![Page 28: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/28.jpg)
Ice melts at 0oC
What happens to themelting point if saltis added?
Ice melts!
![Page 29: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/29.jpg)
Impurities such as salt lowers the meltingpoint of water.
Putting salt on icy roads causes the ice tomelt because it lowers the melting point ofwater.
Impure compounds usually melt lower thanpure compounds so the melting point maybe used as a measure of the purity of acompound
![Page 30: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/30.jpg)
Acetic Acid, CH3COOH,is a colorless liquid thatmelts at 16.6oC.
Let’s look at the melting point ofmixtures of water and acetic acid.
![Page 31: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/31.jpg)
Plot of melting point vs. mole fraction waterfor mixtures of water and acetic acid.
Eutectic point
![Page 32: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/32.jpg)
Cool a acetic acid - water solutionwith a mole fraction water of 0.9
![Page 33: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/33.jpg)
Heat a acetic acid - water solutionwith a mole fraction water of 0.9
![Page 34: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/34.jpg)
Heat a acetic acid - water solutionwith a mole fraction water of 0.2
![Page 35: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/35.jpg)
Pure compounds usually melt overa narrow temperature range, often1o or less.
Impure compounds melt lowerthan pure compounds and over awider temperature range.
![Page 36: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/36.jpg)
m.p. = 115o - 119o m.p. = 118o - 120o m.p. = 121o - 122o
Melting points are a measure of purity
![Page 37: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/37.jpg)
m.p. = 120o - 122o m.p. = 120o - 122o m.p. = 120o - 122o
Two of these bottles contain benzoicacid and one m-nitrophenylacetic acid.
How do you tell what is in each bottle?
![Page 38: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/38.jpg)
Mixed Melting Points
Grind samples together to be sure they aremixed and then measure the melting point.
![Page 39: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/39.jpg)
m.p. = 114o - 117o
m.p. = 120o - 122o
m.p. = 115o - 118o
Mixed 1 and 2
Mixed 1 and 3
Mixed 2 and 3
1 2 3
Results
![Page 40: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/40.jpg)
1. Measure the melting pointof your unknown
2. Run mixed melting pointsto confirm identification
![Page 41: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/41.jpg)
Recrystallization
Impure benzoicacid
Benzoic acid afterrecrystallization
![Page 42: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/42.jpg)
C-OH
O
Benzoic Acid
m.p. = 121 - 122o
![Page 43: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/43.jpg)
Purification of Organic Compounds
Solids: Recrystallization
Liquids: Distillation
Solids and Liquids:
Gas or liquid chromotography
![Page 44: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/44.jpg)
Types of impuritiesSoluble
Insoluble
Partly Soluble
![Page 45: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/45.jpg)
Solubility of benzoic acid in water
![Page 46: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/46.jpg)
Dissolve sample in hot solvent
Compound crystallizes upon cooling
![Page 47: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/47.jpg)
Impure benzoic acid in hot water
![Page 48: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/48.jpg)
Add water and heat until allsoluble material dissolves
Insoluble material is removed by filtration
![Page 49: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/49.jpg)
The hot solution is filtered toremove insoluble impurities
![Page 50: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/50.jpg)
Use fluted filter paper tomaximize surface area.
![Page 51: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/51.jpg)
To avoidcrystallizationin the funnel:
Use GLASS funnel.Put flask on hot plate.
![Page 52: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/52.jpg)
Boil off excess solvent
![Page 53: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/53.jpg)
Boiling Sticks
![Page 54: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/54.jpg)
Hot solutionafter filtration:
Cool Seed Scratch
![Page 55: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/55.jpg)
Crystals form in the warm solution
Next:
Cool, filter, wash, dry, weigh, mp
![Page 56: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/56.jpg)
![Page 57: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/57.jpg)
Buchner funnel..
Filter flask
Heavy-walledtubing
Vacuum
![Page 58: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/58.jpg)
Put filter paper in Buchner funnel..
![Page 59: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/59.jpg)
Filter and wash with cold solvent
![Page 60: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/60.jpg)
Insoluble impurities
Solubleimpurities
Purifiedbenzoic acid
![Page 61: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/61.jpg)
Solubility Example
Compound Solubility g/100 mL
25o 100o
A
I1
I2
1.0
1.5
0.0
80
50
0.0
![Page 62: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/62.jpg)
CompoundSolubility g/100 mL
25o 100o
A
I1
I2
1.0
1.5
0.0
80
50
0.0
A = 10 g I1 = 1.0 g I2 = 1.0 g Total = 12.0 g
100 mL water at 1000
A
I1
I2
dissolves
dissolves
insoluble
![Page 63: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/63.jpg)
CompoundSolubility g/100 mL
25o 100o
A
I1
I2
1.0
1.5
0.0
80
50
0.0
A = 10 g I1 = 1.0 g I2 = 1.0 g Total = 12.0 g
100 mL water at 1000
A dissolves
I1 dissolves
I2 insoluble
Cool to 25o
A
I1
9.0 g crystallize
0 g crystallize
Yield = 100 * 9.0/12.0 = 75%
![Page 64: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/64.jpg)
CompoundSolubility g/100 mL
25o 100o
A
I1
I2
1.0
1.5
0.0
80
50
0.0
A = 10 g I1 = 1.0 g I2 = 1.0 g Total = 12.0 g
50 ml of water at 1000
A
I1
I2
dissolves
dissolves
insoluble
![Page 65: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/65.jpg)
CompoundSolubility g/100 mL
25o 100o
A
I1
I2
1.0
1.5
0.0
80
50
0.0
A = 10 g I1 = 1.0 g I2 = 1.0 g Total = 12.0 g
50 mL water at 1000
A dissolves
I1 dissolves
I2 insoluble
Cool to 25o
A
I1
9.5 g crystallize
0.25 g crystallize
Yield = 100 * 9.75/12.0 = 81%
NOT PURE!
![Page 66: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/66.jpg)
What volume of solvent is needed togive the maximum yield of pure A?
Solubility of I1 = 1.5 g/100 mL
1.5 g100 mL = 1.0 g
x mL
X = (100 mL * 1.0 g)/1.5 g = 67 mL
![Page 67: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/67.jpg)
What is the yield of pure A from 67 mLsolvent?
Solubility of A = 1.0 g/100 mL
1.0 g100 mL = X g
67 mL
X = (67 mL x 1.0 g) / 100 mL = 0.67 g
Yield = 10.0 g - 0.67 g = 9.33 g
% yield = 100 * 9.33 / 12 = 78%
![Page 68: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/68.jpg)
![Page 69: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/69.jpg)
Boiling Points - Distillations
Ethylene glycol,HOCH2CH2OH, boils at198oC and melts at -13o C.
What happens to the meltingpoint of water if you addantifreeze?
Melting point goes down.
![Page 70: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/70.jpg)
What happens to theboiling point of water ifyou add antifreeze?
The boiling point goes up.
![Page 71: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/71.jpg)
Mixtures
Solids Usually melt low
LiquidsUsually boilbetween the twocomponents
![Page 72: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/72.jpg)
Vapor pressure of water vs. temperature
Solution boils when the vapor pressure =applied pressure
![Page 73: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/73.jpg)
If you add salt, NaCl,to water what happensto the melting point?
Impurities depressthe melting point soit goes down.
![Page 74: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/74.jpg)
If you add salt, NaCl,to water what happensto the boiling point?
The boiling pointgoes up.
![Page 75: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/75.jpg)
Raoult’s Law
o
ObservedPressure
Pure Substance
Mole Fraction
![Page 76: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/76.jpg)
C
O
CH3CH3
Acetoneb.p = 56o Benzene
b.p. = 80o
Two Volatile Liquids
![Page 77: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/77.jpg)
Two Volatile LiquidsPa = Po
a * Naa
Pb = Pob * Nbb
Mixture boils when
Pa + Pb = Papplied
![Page 78: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/78.jpg)
Plot of boiling point vs. mole fractionfor a mixture of acetone and benzene.
![Page 79: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/79.jpg)
Boiling point of an acetone-benzene mixturewith a mole fraction benzene of 0.50
What is the composition of the vapor?
![Page 80: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/80.jpg)
Vapor richer in the lower boiling component
![Page 81: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/81.jpg)
Fractional Distillation
![Page 82: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/82.jpg)
![Page 83: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/83.jpg)
Packed Column
HETP = 1.5 cm
![Page 84: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/84.jpg)
Vigreux Column
HETP = 10 cm
![Page 85: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/85.jpg)
CH3OHmethyl alcoholmethanolb.p. = 64.7o
H2Owaterb.p. = 100o
ExperimentSeparate mixture of methanol and water.Plot volume distilled vs. temperature.
![Page 86: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/86.jpg)
![Page 87: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/87.jpg)
CH3OH
Methyl alcohol is toxic!
![Page 88: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/88.jpg)
Standard Taper Joints
14/20
20 mm
14 mm
![Page 89: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/89.jpg)
Grease joints toprevent sticking.
![Page 90: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/90.jpg)
![Page 91: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/91.jpg)
Plug the thermowell into thevariable transformer
![Page 92: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/92.jpg)
Put boiling chips in bottom of flask
Boiling Chips
![Page 93: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/93.jpg)
![Page 94: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/94.jpg)
ThermometerAdapter
![Page 95: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/95.jpg)
Water in
Water out
![Page 96: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/96.jpg)
![Page 97: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/97.jpg)
IDEAL MIXTURES:
Same interactions between likeand unlike molecules
NONIDEAL MIXTURES:
Strong attractions between likemoleculesStrong attractions between unlikemolecules
A.
B.
![Page 98: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/98.jpg)
Ethanol - Benzene
Minimum - boiling azeotrope
![Page 99: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/99.jpg)
![Page 100: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/100.jpg)
Acetone - Chloroform
Maximum-boiling azeotrope
![Page 101: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/101.jpg)
![Page 102: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/102.jpg)
Simple Distillation
![Page 103: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/103.jpg)
![Page 104: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/104.jpg)
![Page 105: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/105.jpg)
![Page 106: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/106.jpg)
Extractions
Mixture of benzoic acid, anthracene, andp-nitroaniline
![Page 107: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/107.jpg)
COHO
NH2
NO2
![Page 108: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/108.jpg)
Mixture of methylene chloride and water
Density of CH2Cl2 is 1.33 g/mL
CH2Cl2
H2O
![Page 109: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/109.jpg)
If we dissolve NaCl in this mixturewhich phase has the highest saltconcentration?
Salts concentrate inthe water layer
![Page 110: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/110.jpg)
If we dissolve benzoic acid in thismixture in which phase would itconcentrate?
Neutral organiccompounds concentrate inthe organic phase
Salts
![Page 111: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/111.jpg)
Salts in water phase
Neutral organiccompounds in theorganic phase
Water
CH2Cl2
![Page 112: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/112.jpg)
COOH + Na OH COO Na
Benzoic Acid Sodium Benzoate
Treatment of benzoic acid withsodium hydroxide converts itinto the salt, sodium benzoate.
![Page 113: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/113.jpg)
COOH + Na OH COO Na
![Page 114: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/114.jpg)
NH3 + HCl NH4+ Cl-
Base Acid Salt
![Page 115: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/115.jpg)
NH2O2N + HCl NH3O2N Cl
![Page 116: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/116.jpg)
Use separatory funnel for separations.
![Page 117: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/117.jpg)
Shake to be surephases equilibrate
Hold stopperand stopcock
![Page 118: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/118.jpg)
![Page 119: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/119.jpg)
benzoic Acid
p-nitroaniline
anthracene
HCl CH2Cl2
NH3O2N ClBenzoic acid
Anthracene
![Page 120: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/120.jpg)
benzoic Acid
anthracene
NaOH CH2Cl2
COO Na anthracene
![Page 121: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/121.jpg)
NH3O2N Cl COO Na
NH2O2N
NaOH
COOH
Filterwashdryweigh
HCl
Filterwashdryweigh
Dryfilterevaporate
weigh
![Page 122: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/122.jpg)
Addition of acid tothe sodiumbenzoate solutioncauses benzoic acidto precipitate.
![Page 123: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/123.jpg)
The benzoic acid isfiltered, washed,and dried.
![Page 124: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/124.jpg)
Weigh the benzoicacid and measure itsmelting point.
![Page 125: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/125.jpg)
NH2O2NNH3O2N ClNaOH
Cool to complete precipitation
![Page 126: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/126.jpg)
Dry the methylene chloride solutionof anthracene with a small amountof sodium sulfate.
![Page 127: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/127.jpg)
Remove the drying agent by filtrationthrough a fluted filter paper.
![Page 128: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/128.jpg)
Evaporate themethylene chlorideon a steam bath.
Use an invertedfunnel connected tothe vacuum line tocollect the vapor.
![Page 129: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/129.jpg)
Weigh your products and measuretheir melting points.
Put your samples in labeled vialsand give them to your TA.
![Page 130: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/130.jpg)
10 g t-butyl alcohol100 mL ether100 mL water
Partition Coefficients
![Page 131: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/131.jpg)
2.2 = x g / 200 mL
( 10 - x)g /100 mL
x = 8.1 grams
10 grams t-butyl alcohol
![Page 132: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/132.jpg)
Which is better?
Extract once with 200 mL or twice with 100 mL?
![Page 133: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/133.jpg)
If K = 1.0, a = 10 grams, S2 = 100 mL
Extract once with 200 mL yields 6.7 grams
Extract once with 100 mL yields 5.0 gramsSecond extraction with 100 mL yields 2.5 gramsTotal 2 extractions with 100 mL = 7.5 grams
![Page 134: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/134.jpg)
Grams extracted vs. number of extractionsfor K = 1, 2 and 4
![Page 135: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/135.jpg)
Preparation of t-butyl chloride(2-chloro-2-methylpropane)
CCH3
CH3CH3
OHHCl
CCH3
CH3CH3
Cl + H2O
t-butyl alcohol t-butyl chloride
![Page 136: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/136.jpg)
(CH3)3COH + HCl
(CH3)3CCl + H2O
Reaction Mechanism?
![Page 137: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/137.jpg)
(CH3)3COH + H-Cl
(CH3)3COH2 + Cl + -
Leaving Group
![Page 138: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/138.jpg)
(CH3)3C-OH2 +
(CH3)3C + H2O
Cation
![Page 139: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/139.jpg)
(CH3)3C + + Cl-
(CH3)3CCl
![Page 140: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/140.jpg)
C CH3
CH3
CH3
tert-Butyl Cation
+sp2 flat
p
![Page 141: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/141.jpg)
![Page 142: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/142.jpg)
2
Transition State
δ δ
![Page 143: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/143.jpg)
![Page 144: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/144.jpg)
Substitution
Nucleophilic
1 bondat a time
![Page 145: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/145.jpg)
Increasing Stability
![Page 146: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/146.jpg)
Main Reaction
Side Reaction
CCH3
CH3CH3
OHHCl
CCH3
CH3CH3
Cl + H2O
t-butyl alcohol t-butyl chloride
CCH3
CH3CH3
OHHCl
+ H2O
t-butyl alcohol
CH2CCH3
CH3
isobutylene
![Page 147: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/147.jpg)
CH2CCH3
CH3
C
CH3
CH3CH3
CCH3
CH3CH3
Cl
E1 N
![Page 148: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/148.jpg)
ProcedureShake t-BuOH with concentrated HCl
Separate layers
Wash saturated aqueous NaCl
Wash saturated aqueous NaHCO3
Dry
Distill
![Page 149: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/149.jpg)
t-BuCl
Shake t-BuOH with HCl
![Page 150: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/150.jpg)
NaHCO3 + HCl
CO2 + H2O + NaCl
Wash to remove excess HCl
![Page 151: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/151.jpg)
Distill product
Cool receiver
![Page 152: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/152.jpg)
Clamp joints
![Page 153: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/153.jpg)
Yield Calculations
A + B CMW 100 100 200
Use: 10 g A 20 g B
Limiting Reagent
Theoretical Yield
Experimental Yield
![Page 154: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/154.jpg)
A + B CMW 100 100 200
Cpd Mass MW Moles
A 10 g 100 0.10
B 20 g 100 0.20
Theoretical yield:0.10 moles x 200 = 20 g
Experimental yield (%):100 x wt product / 20
LimitingReagent
![Page 155: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/155.jpg)
CH3CH2CH2CH2OH n-butyl alcohol
HBr
CH3CH2CH2CH2Brn-butyl bromide
![Page 156: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/156.jpg)
RCH2OH + H+ RCH2OH2+
C
R
HHOH2Br
δ− δ+
transition state
RCH2Br
![Page 157: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/157.jpg)
![Page 158: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/158.jpg)
Substitution
Nucleophilic
2 bonds ata time
![Page 159: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/159.jpg)
Methyl Benzoate
CO
OCH3
![Page 160: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/160.jpg)
CO
OH + CH3OHH2SO4
Esterification
Benzoic acidMethanol
Methyl benzoate
CO
OCH3 + H2O
![Page 161: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/161.jpg)
C6H5-COH
OH+
C6H5-C
OH
OH
OCH3
H
C6H5-C-O
OH
OH
CH3
HC6H5-C-OCH3
OH
OH
C6H5-C-OCH3
OH
OHH
C6H5-COH
OCH3C6H5-C
OCH 3
OH+
![Page 162: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/162.jpg)
COH
OHC
OH
OH
COH
OH
Resonance Stabilized Ion
![Page 163: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/163.jpg)
C6H5-C-OCH3
OH
OH
Intermediate
COH
O
C6H5 COCH3
O
C6H5
![Page 164: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/164.jpg)
Reflux the mixturefor 60 minutes.
Methanol
Benzoic Acid
Sulfuric Acid
Boiling chips
![Page 165: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/165.jpg)
CO
OCH3CO
OH + CH3OHH2SO4
+ H2O
Equilibrium
K = [C6H5COOCH3][H2O]
[C6H5COOH][CH3OH]
![Page 166: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/166.jpg)
CO
OCH3CO
OH + CH3OHH2SO4
+ H2O
Measure Equilibrium Constant
Recover benzoicacid at equilibrium
Isolate and purifiymethyl benzoate
![Page 167: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/167.jpg)
C6H5COOH CH3OH H2SO4
Reflux, Cool,Extract withCH2Cl2, H2O
CH2Cl2 H2O
H2SO4C6H5COOCH3C6H5COOH
![Page 168: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/168.jpg)
C6H5COOCH3C6H5COOH
Extract withNaHCO3
CH2Cl2 H2O
C6H5COOCH 3 C6H5COO Na- +
![Page 169: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/169.jpg)
C6H5COOCH 3
Dry
Filter
Distill
Weigh
Methyl benzoate product
![Page 170: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/170.jpg)
Simple Distillation
![Page 171: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/171.jpg)
C6H5COO Na- +
HCl
C6H5COOH
FilterWashDryWeighmp
Benzoic Acid Product
![Page 172: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/172.jpg)
CO
OCH3CO
OH + CH3OHH2SO4
+ H2O
K = [C6H5COOCH3][H2O]
[C6H5COOH][CH3OH]
Calculate K
Initial benzoic acid = Ao
Initial Methanol = Mo
Recovered benzoic acid = A
![Page 173: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/173.jpg)
CO
OCH3CO
OH + CH3OHH2SO4
+ H2O
Initial: Ao Mo
Equ: Ao - x Mo - x x x
X = Ao - A(recovered)
K =[x][x]
[Ao - x][Mo - x]
![Page 174: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/174.jpg)
CO
OCH3CO
OH + CH3OHH2SO4
+ H2O
Example
Ao = 0.100 moles Mo = 0.500 moles
A(Recovered) = 0.010 moles
x = 0.100 - 0.010 = 0.090 moles
K = [0.090][0.090][0.100 - 0.090][0.500 - 0.090] = 1.7
![Page 175: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/175.jpg)
Nitration of Methyl Benzoate
COOCH3
HNO3, H2SO4
COOCH3
NO2
COOCH3COOHCH3OH
H2SO4
![Page 176: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/176.jpg)
Multistep Synthesis
A B C50% 50%
Yield = 25%
![Page 177: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/177.jpg)
(CH3)3COH (CH3)3ClHCl
Nucleophilic Aliphatic Substitution
NO2+
+
H NO2
Electrophilic Aromatic Substitution
![Page 178: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/178.jpg)
ARENE SUBSTITUTION
H EE+
+ H+
The electrophile REPLACES H+
![Page 179: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/179.jpg)
H E - Y H E
+
![Page 180: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/180.jpg)
H E - Y H E
+
H E
+
H E
+
H E
+
E
+ H+
![Page 181: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/181.jpg)
H E
+
H E
+
H E
+
![Page 182: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/182.jpg)
![Page 183: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/183.jpg)
Nitration of BenzeneNO2
HNO3
H2SO4
Nitrobenzene
![Page 184: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/184.jpg)
Nitration Reagent
Nitronium Ion
HONO2 + 2 H2SO4 NO2+ + H3O+ + 2 HSO4
-
![Page 185: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/185.jpg)
HNO2
+ H NO2
+
NO2
+ H+
![Page 186: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/186.jpg)
Multiple SubstituentsG
G G
G
Second Group. Where go? How fast?
![Page 187: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/187.jpg)
Nitration of TolueneCH3
CH3NO2
CH3
NO2
CH3
NO2
HNO3
63% 3% 34%
![Page 188: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/188.jpg)
CH3NO2
H
CH3NO2
H
CH3NO2
H+
+ +
CH3
NO2
H
CH3
NO2
H
CH3
NO2
H
CH3
NO2H
CH3
NO2H
CH3
NO2H
+
+
+
+ ++
ORTHO
META
PARA
![Page 189: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/189.jpg)
G
Electron donating groups favorreaction ORTHO and PARA.
Electron Donating
Ortho
Para
![Page 190: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/190.jpg)
CF3
Nitration of (trifluoromethyl)benzene
HNO3
H2SO4
CF3
NO2
CF3
NO2
CF3
NO2
6% 91% 3%
![Page 191: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/191.jpg)
CF3
Electron Withdrawing group
+ chargehere bad
![Page 192: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/192.jpg)
CF3HNO2
CF3H
NO2
CF3H
NO2
CF3
H
NO2
CF3
H
NO2
CF3
H
NO2
CF3
H NO2
CF3
H NO2
CF3
H NO2
Ortho
Meta
Para
++ +
+
+
+
+ ++
![Page 193: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/193.jpg)
Z
Electron Withdrawing Groups areMeta Directors and DEACTIVATING
ElectronWithdrawingGroup
Meta Product
![Page 194: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/194.jpg)
COOCH3
HNO3, H2SO4
COOCH3
NO2
Main Reaction
Side Products
meta
COOCH3NO2
NO2
COOCH3 COOCH3
NO2O2N
![Page 195: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/195.jpg)
Procedure
1. Dissolve methyl benzoate in H2SO4
2. Mix HNO3 and H2SO4 at 0oC
3. Add HNO3 / H2SO4 dropwise to methyl benzoate at 0oC
![Page 196: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/196.jpg)
4. Let stand at roomtemperature 10minutes
5. Pour onto ice
![Page 197: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/197.jpg)
Filter
![Page 198: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/198.jpg)
Wash
Recrystallize frommethanol
Dry
Weigh
m.p.
![Page 199: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/199.jpg)
Dehydration of Alcohols
OH
H+ H2O
H2SO4
cyclohexanol cyclohexene
![Page 200: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/200.jpg)
Elimination Reactions
C - C
X
Y
To make C=C need to eliminate X, Y.
![Page 201: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/201.jpg)
C - C
X
Y
3 ways to break 2 bonds1. Concerted (x and y leave same time)2. X leaves first3. Y leaves first
![Page 202: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/202.jpg)
CC
H
OH H2SO4CC
H
OH2+
CC
H
OH2+
CC
H
+
Leaving Group
![Page 203: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/203.jpg)
CC
H
+
base
CC
![Page 204: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/204.jpg)
![Page 205: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/205.jpg)
R-X R+ + X-
Alkene + H+
![Page 206: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/206.jpg)
Elimination 1 bondat a time
![Page 207: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/207.jpg)
+
Substitution
Elimination
Rearrangement
SN1E1
![Page 208: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/208.jpg)
CH2CCH3
CH3
C
CH3
CH3CH3
CCH3
CH3CH3
Cl
E1 N
![Page 209: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/209.jpg)
Dehydrohalogenation
C - C
X
H
Strong base
![Page 210: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/210.jpg)
C - C
X
H
What is the mechanism of dehydrohalogentation?
C - C
X
D
C-D bond stronger than C-H bond.
![Page 211: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/211.jpg)
C-CH2Br
H
H
CH=CH2
NaOEt
C-CH2Br
D
DNaOEt
CD=CH2
Isotope Effect
kH/kD = 7
![Page 212: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/212.jpg)
Isotope effect shows thatC-H bond broken in thetransition state.
![Page 213: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/213.jpg)
Element Effect
C - CX
H
Change Element
![Page 214: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/214.jpg)
SYN vs. ANTI Elimination
C - CX
H
C - C
H X
Same Side Opposite Side
![Page 215: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/215.jpg)
H
C6H5CH3C6H5H
Br
H
C6H5CH3Br
HC6H5
C6H5
C6H5
CH3
H
![Page 216: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/216.jpg)
![Page 217: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/217.jpg)
Transition State
Product
StartingMaterial
Energy
![Page 218: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/218.jpg)
Elimination 2 Bonds ata time
![Page 219: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/219.jpg)
OH
H+ H2O
H2SO4
cyclohexanol cyclohexene
Procedure
![Page 220: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/220.jpg)
• Put cyclohexanol and sulfuric acid inround bottom flask
• Fractional Distillation (steamdistillation) collect distillate 80-85o
• Dry product with K2CO3
4. Distill
![Page 221: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/221.jpg)
Distil immiscible liquids
PT = PA + PB
(Steam Distillation)
![Page 222: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/222.jpg)
Baeyer Unsaturation Tests
PotassiumPermanganate
KMnO4
![Page 223: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/223.jpg)
R2C=CR2 + MnO4- H2O
purplealkene
R2C - CR2
OH OH
+ MnO2
darkbrown
glycol
![Page 224: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/224.jpg)
Br2
Br
Br
BrBr
![Page 225: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/225.jpg)
Bromine and Cyclohexene
![Page 226: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/226.jpg)
![Page 227: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/227.jpg)
Anisalacetophenone
CH3O CHO
Anisaldehyde
+ CH3CO
Acetophenone
CCH C
H
CH3O
O
trans-anisalacetophenone
NaOH
![Page 228: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/228.jpg)
Nucleophilic Aliphatic Substitution
RX + Y- RY + X-
EsterificationArCOOH + ROH ArCOOR + H 2O
Electrophilic Aromatic Substitution
ArH ArNO2HNO3
H2SO4
Aldol Condensation
Make new C-C bond
![Page 229: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/229.jpg)
R-C OH
O
Carboxylic Acid
Acidic Hydrogen
![Page 230: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/230.jpg)
R-C
O
C
H
Acidic Hydrogen
![Page 231: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/231.jpg)
R-C
O
OR-C
O
O
R-C
O
C CR-C
O
![Page 232: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/232.jpg)
C
OC
O -
+
Polar Carbonyl Group
![Page 233: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/233.jpg)
C
O
C
O -
Y- Y
Nucleophilic Addition to Carbonyl Group
![Page 234: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/234.jpg)
CCH3
O OH-
C CH2
O-
CO
CH2
-
![Page 235: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/235.jpg)
OCH3CHO
C CH2
OCH
OOCH3
-
![Page 236: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/236.jpg)
C CH2
OCH
OHOCH3
C CHO
CH OCH3
![Page 237: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/237.jpg)
Side Reactions:
C
O
CH2
-+ CCH3
O
C CH2
OCCH3
OH
C CHO
CCH3
![Page 238: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/238.jpg)
CH3O C HO
+ OH- CH3O C
OHH
O-
CH3O COH
HO-
OCH3CO
H
CCH3O OHO
OCH3CHH
OH
Cannizzaro Reaction
![Page 239: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/239.jpg)
ProcedureGet sample of acetophenonefrom storeroom
Locate p-anisaldehyde inhood
Measure sample of ansialdehyde
![Page 240: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/240.jpg)
Dissolve anisaldehyde andacetophenone in 95% ethanol
Dissolve NaOHin water
Mix and allow tostand for about10 minutes
![Page 241: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/241.jpg)
Cool
Filter
Wash
![Page 242: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/242.jpg)
Recrystallize
Weigh
m.p.
![Page 243: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/243.jpg)
Type of compound:Aldehyde
Alcohol
Amine
Ketone
Identify an Unknown
![Page 244: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/244.jpg)
Procedure
1. Physical PropertiesMelting point or boiling point
2. Functional Group
Infrared spectrum
NMR Spectrum
Solubility
Classification Tests
3. Solid Derivative
![Page 245: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/245.jpg)
Measure boilingpoint of liquids
![Page 246: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/246.jpg)
Functional GroupCarbonyl Group (1650 - 1725 cm-1)?
Yes No
AldehydeKetone
NMR
Aldehyde Ketone+ -
AlcoholAmine
BroadOH in IR
Yes NoAlcohol Amine
(Basic?)3700 - 4000 cm-1
YesPrimary or Secondary
NoTertiary
![Page 247: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/247.jpg)
2,4-dinitrophenylhydrazine test
NH2NH
NO2
NO2
Aldehyde or ketone
![Page 248: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/248.jpg)
R-C-R
O+ NH2NH
NO2
NO2
NNH
NO2
NO2CR
R
2,4-dinitrophenylhydrazone
![Page 249: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/249.jpg)
C
ONH2R C
OH
NHR
NRC
![Page 250: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/250.jpg)
Iodoform TestReagent: NaOH and I2 (NaOI)
CCH3
O
RI2, NaOH
RCOOH + CHI 3Yellow
![Page 251: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/251.jpg)
CCH3
O
RI2, NaOH
RCOOH + CHI3Yellow
Iodoform Test
CHCH3
OH
RI2, NaOH
RCOOH + CHI3Yellow
![Page 252: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/252.jpg)
![Page 253: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/253.jpg)
Amines
1. Odor
2. If not soluble in water they maydissolve in dilute aqueous acid (HCl).
3. Water solutions of amines arebasic to litmus.
![Page 254: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/254.jpg)
Hinsberg Test for Amines
SO2Cl
Benzenesulfonyl Chloride
![Page 255: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/255.jpg)
Hinsberg Test for Amines
Primary: Soluble. PPT if add HClSecondary: Insoluble
Tertiary: Tends not to react
![Page 256: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/256.jpg)
DerivativesAldehydes and Ketones
1. 2,4-dinitrophenylhydrazone
2. Semicarbazone
NH2NHC
O
NH2
semicarbazide
+ RC
O
R NNHCNH2CR
RO
semicarbazone
![Page 257: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/257.jpg)
Alcohol Derivative
O2N
O2N
C ClO
O2N
O2N
C OROROH
3,5-dinitrobenzoyl chloride
3,5-dinitrobenzoate
![Page 258: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/258.jpg)
Amine DerivativesPrimary and Secondary Amines
CO
Cl + RNH2 CO
NHR
Benzoyl Chloride Benzamide
SO2Cl + RNH2 SO2NHR
Benzenesulfonyl Chloride Benzenesulfamide
![Page 259: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/259.jpg)
Sample Unknown
B.p. =198-200o
DNP = 231-235o
![Page 260: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/260.jpg)
![Page 261: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/261.jpg)
C
O
CH3
acetophenone
![Page 262: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/262.jpg)
Sample Unknown
B.p. = 80 - 85o
3,5-dinitrobenzoate= 119 - 121o
![Page 263: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/263.jpg)
![Page 264: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/264.jpg)
CCH3 CH3
H
OH
isopropyl alcohol
![Page 265: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/265.jpg)
B.p = 106o
3,5-dinitrobenzoate85o
![Page 266: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/266.jpg)
![Page 267: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/267.jpg)
CH2OHCH
CH3
CH3
isobutyl alcohol
![Page 268: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/268.jpg)
B.p. = 160o
3,5-dinitrobenzoate:108-110o
![Page 269: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/269.jpg)
![Page 270: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/270.jpg)
OH
H
cyclohexanol
![Page 271: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/271.jpg)
B.p. = 155-157o
2,4-DNP = 158 -160o
![Page 272: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/272.jpg)
![Page 273: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/273.jpg)
O
cyclohexanone
![Page 274: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/274.jpg)
B.p. = 180 -183o
Benzenesulfonamide110 - 112o
Benzamide 160 - 163o
![Page 275: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/275.jpg)
![Page 276: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/276.jpg)
NH2
aniline
![Page 277: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/277.jpg)
Infrared Spectroscopy
Identify the functional group(s)
![Page 278: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/278.jpg)
Electromagnetic Spectrum
![Page 279: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/279.jpg)
Energy
Amplitude
absorption radiation
Bond Vibrations
![Page 280: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/280.jpg)
CH
HC
H
HBending
CH
HC
H
HStretching
![Page 281: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/281.jpg)
Classical IR Spectrometer
![Page 282: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/282.jpg)
![Page 283: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/283.jpg)
NaClNaCl IR Plates IR Plates
A drop of sample is place between the NaCl plates
![Page 284: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/284.jpg)
NaCl cell for solutions
![Page 285: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/285.jpg)
![Page 286: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/286.jpg)
Wavenumber cm-1
E = h�= hc/ν λ
![Page 287: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/287.jpg)
Characteristic IR Absorption Frequencies
C-H Alkanes 2850-2960C-H Alkenes 3020-3080C-H Arenes 3000-3100
C-O Alcohols, ethers 1080-1300
C=O Aldehydes, ketones... 1690-1760
O-H Alcohols 3200-3600Acids 2500-3000
N-H Amines 3300-3500
cm-1Bond
![Page 288: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/288.jpg)
-OH
C-H
-O-R
Alcohol
![Page 289: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/289.jpg)
PrimaryAmine
-NH2
![Page 290: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/290.jpg)
N-H
![Page 291: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/291.jpg)
C=O
![Page 292: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/292.jpg)
Aldehyde
C=O
RCO-H
![Page 293: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/293.jpg)
Carboxylic Acid
OH
C=O
![Page 294: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/294.jpg)
C=OC-O
![Page 295: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/295.jpg)
Carbonyl group -- Ketone
Functional Group?
![Page 296: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/296.jpg)
Alcohol
Functional Group?
![Page 297: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/297.jpg)
Carboxylic Acid
Functional Group?
![Page 298: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/298.jpg)
Ester
Functional Group?
![Page 299: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/299.jpg)
amine (secondary)
Functional Group?
![Page 300: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/300.jpg)
C6H5COCH3
C8H8O
![Page 301: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/301.jpg)
isopropyl alcohol
C3H8O
![Page 302: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/302.jpg)
CH3COOCH2CH3
C4H8O2
![Page 303: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/303.jpg)
CH3COCH2CH2CH3
C5H10O
![Page 304: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/304.jpg)
NuclearMagneticResonance
Chapter 13
![Page 305: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/305.jpg)
Proton Nuclear Spin States
Two states have the same energyin the absence of a magnetic field
MagneticField
![Page 306: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/306.jpg)
Protons in an external magnetic field
Energy difference between the spin-statesdepends on the strength of the magnetic field.
![Page 307: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/307.jpg)
NMR Spectrometer
![Page 308: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/308.jpg)
Superconducting NMR Magnet
![Page 309: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/309.jpg)
NMR Sample Tubes
![Page 310: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/310.jpg)
NMR Probe
Sample goesin here
CoilsInsulated tube
![Page 311: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/311.jpg)
![Page 312: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/312.jpg)
![Page 313: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/313.jpg)
![Page 314: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/314.jpg)
NMRSignal
Proton NMR Spectrum of Cl3CH
Magnetic Field
![Page 315: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/315.jpg)
H
Ho
Field here less than Ho
![Page 316: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/316.jpg)
Electrons shield nucleus fromexternal magnetic field.
Magnetic field
![Page 317: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/317.jpg)
E = H
Energy to change spin stateproportional to field strength
E =h
Measure field strength in FREQUENCYunits
Cycles/second
γ
ν
![Page 318: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/318.jpg)
Si CH3
CH3
CH3
CH3
Tetramethylsilane
TMSReference compound for NMR spectrum.
![Page 319: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/319.jpg)
NMRsignal
Magnetic Field
Cl3CH
TMS
437 Hzat 60x106 Hz
![Page 320: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/320.jpg)
Chemical Shift =Position of Signal - Position of TMS
Spectrometer Frequencyx106
Units = parts per million = ppm
Chemical Shift Scale
=437 Hz - 0 Hz60x106Hz
x 106 = 7.28 ppmδ
δ
![Page 321: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/321.jpg)
Typical Chemical Shifts
CR H
CO
C H
CCl H
CBr H
CO H
0.9 - 1.8
2.1 - 2.5
3.1 - 4.1
2.7 - 4.1
3.3 - 3.7
![Page 322: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/322.jpg)
C H
CCH
H
CO
H
HOR
Typical Chemical Shifts
2.3 - 2.8
4.5 - 6.5
6.5 - 8.5
9 - 10
0.5 - 5
![Page 323: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/323.jpg)
10 9 8 7 6 5 4 3 2 1 0
TMSRHC-C-HO
C HXC = CH
H
C H
O
Proton Chemical Shifts
ppm down field from TMS
![Page 324: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/324.jpg)
![Page 325: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/325.jpg)
![Page 326: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/326.jpg)
Area proportional to number of protons
![Page 327: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/327.jpg)
How many lines would youexpect in the proton NMRspectrum of this compound?
![Page 328: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/328.jpg)
![Page 329: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/329.jpg)
C C
H H
X
Measure signalfrom this proton
Field from this protoncan be aligned oropposed to appliedfield
Magnetic Field
![Page 330: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/330.jpg)
Spin Combinations - 2 adjacent protons
-C-CH2-H
1 : 2 : 1
![Page 331: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/331.jpg)
Spin Combinations - 3 AdjacentProtons
-C-CH3
H
1: 3: 3: 1
![Page 332: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/332.jpg)
Adjacent Protons Lines
123
234
![Page 333: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/333.jpg)
![Page 334: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/334.jpg)
What is the name of this compound?
Ethyl Bromide
![Page 335: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/335.jpg)
![Page 336: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/336.jpg)
CH3CO
OCH2CH3
![Page 337: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/337.jpg)
![Page 338: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/338.jpg)
![Page 339: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/339.jpg)
![Page 340: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/340.jpg)
![Page 341: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/341.jpg)
ICH2CH2CH3
![Page 342: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/342.jpg)
![Page 343: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/343.jpg)
![Page 344: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/344.jpg)
![Page 345: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/345.jpg)
![Page 346: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/346.jpg)
![Page 347: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/347.jpg)
What is this compound?
CH3COCH2CH3
![Page 348: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/348.jpg)
C6H5COCH3
What is this compound?
![Page 349: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/349.jpg)
What is this compound?
C6H5COOCH2CH3
![Page 350: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/350.jpg)
y
x
Magneticfield changesacross sample
![Page 351: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/351.jpg)
13Common nuclei which have a magnetic moment:
1H13C15N19F
(Odd mass number or even mass number and odd atomic number)
![Page 352: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/352.jpg)
Only 1.1% of the carbonatoms in a sample are C13
C12 does not have a magneticmoment.
![Page 353: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/353.jpg)
CCC HH
H
H
HH
H
H
13
Signal weakNo C-C couplingStrong C-H couplingLarge Chemical Shifts
C13 NMR
![Page 354: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/354.jpg)
C13 Chemical Shifts
RCH3
R2CH2
RCH2Cl
R3CH
CC
CC
OC
0 - 35
15 -40
25 - 50
25 - 50
65 - 90
100 - 150
110 - 175
190 - 220
ppm from TMS
![Page 355: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/355.jpg)
COCH2CH3
OCH3CH2
Proton NMR Spectrum
![Page 356: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/356.jpg)
Carbon NMR Spectrum
COCH2CH3
OCH3CH2
(Proton Decoupled)
![Page 357: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/357.jpg)
CHCH2CH3
OHCH3
Peak height (area) NOT proportionalto number of C atoms.
![Page 358: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/358.jpg)
Proton decoupled CMR
![Page 359: Stan Smith - University of Illinois Archivesarchives.library.illinois.edu/erec/University Archives/1505050...Stan Smith sg-smith@uiuc.edu. . User Name: netID ... Identify a compound](https://reader031.fdocuments.net/reader031/viewer/2022030710/5af89ee67f8b9a2d5d8bd3de/html5/thumbnails/359.jpg)
Proton coupled CMR