CEM 252, Fall 2009 Tue, Thurs 8:00–9:20 am Midterm #2 ......CEM252, Fall 2009 Midterm #2 2...
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CEM252, Fall 2009 Midterm #2 1 CEM 252, Fall 2009 Tue, Thurs 8:00–9:20 am Midterm #2 October 29, 2009 Name:______________________________ PID: _______________________________ Section:____________ TA: _______________ This is a closed book and note examination. If boxes are provided for your answers, only what is written in the boxes will be graded. You have 80 minutes to complete the test. Section 1 M 8:00 – 8:50 AM Roozbeh Section 2 W 8:00 – 8:50 AM Aman Section 3 W 1:50 – 2:40 PM Aman Section 4 M 11:30 – 12:20 PM Roozbeh Section 5 F 9:10 – 10:00 AM Wenjing Section 6 M 11:30 – 12:20 AM Atefeh Section 7 F 3:00 – 3:50 PM Wenjjing Section 8 M 9:10 – 10:00 AM Roozbeh Section 9 Th 4:10 – 5:00 PM Atefeh Section 10 F 8:00 – 8:50 AM Wenjing Section 11 W 9:10 – 10:00 AM Aman Section 12 Th 1:50 – 2:40 PM Atefeh Question Points Score 1 8 2 10 3 6 4 5 5 6 6 3 7 6 8 6 9a 16 9b 16 10a 6 10b 6 10c 6 Total 100
Transcript of CEM 252, Fall 2009 Tue, Thurs 8:00–9:20 am Midterm #2 ......CEM252, Fall 2009 Midterm #2 2...
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CEM252, Fall 2009 Midterm #2
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CEM 252, Fall 2009 Tue, Thurs 8:00–9:20 am
Midterm #2 October 29, 2009
Name:______________________________ PID: _______________________________
Section:____________ TA: _______________
This is a closed book and note examination. If boxes are provided for your answers, only what is written in the boxes will be graded. You have 80 minutes to complete the test.
Section 1 M 8:00 – 8:50 AM Roozbeh Section 2 W 8:00 – 8:50 AM Aman Section 3 W 1:50 – 2:40 PM Aman Section 4 M 11:30 – 12:20 PM Roozbeh Section 5 F 9:10 – 10:00 AM Wenjing Section 6 M 11:30 – 12:20 AM Atefeh Section 7 F 3:00 – 3:50 PM Wenjjing Section 8 M 9:10 – 10:00 AM Roozbeh Section 9 Th 4:10 – 5:00 PM Atefeh Section 10 F 8:00 – 8:50 AM Wenjing Section 11 W 9:10 – 10:00 AM Aman Section 12 Th 1:50 – 2:40 PM Atefeh
Question Points Score 1 8 2 10 3 6 4 5 5 6 6 3 7 6 8 6 9a 16 9b 16 10a 6 10b 6 10c 6
Total 100
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1. Provide a name or a structure for the following compounds (2 pts each, 8 pts) a. b. Cyclopentane carboxylic acid c. Ethyl hexanoate d. 2. Match the following names with their appropriate structures (write the letter corresponding to the structure beside the given name) (NOTICE there are more structures than names and ONLY 1 correct answer) (2 pts each, 10 pts)
Name Letter Benzophenone Benzonitrile Acetic acid Lactam Succinic Anhydride
O
O
O
O
NH
A B C
K
E
F G H
I
D
J
O
O
NO
OO
CNCN
OH
O
H H
O
H
O
L
O
O
O
O
O
O
O
O
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3. Draw an example of any compound containing the indicated functional group (2 pts each, 6 pts) 4. Put the following acid derivatives in order of decreased activity towards nucleophilic substitution (5 pts)
Any tertiary amide
Any Imine Any Acetal
Bonus Question (2 pts): Is the leaving group of the LEAST reactive acid derivative a :
weak base or strong base?
O
O
Cl
O
O
O
NH
O
OH
OO
A B C D E
most reactive least reactive
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5. Circle the correct answer. (2 pts each, 6 pts) a. Which of the following nucleophiles will do an (1,4) addition onto an α,β-unsaturated aldehyde or ketone? b. Which of the following carboxylic acids is the strongest (lowest pKa)? c. The following reaction can be categorized as: 6. As written the following synthesis has a flaw. What is wrong with it? (3 pts)
O
O 1. DIBALH, -78 C
2. H3O+
3. TMSCl, pyr
OTMS
MgBr OH NH2 HO
OH
O
OH
O
OH
O
OH
O
Br
BrBr
Br
Br
Br
Cl
O
OH
+ O
O
AlcoholysisAminolysis Hydrolysis Reduction
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7. Show a detailed mechanism of the following transformation. (6 pts)
O
CH3NH2
H+
N
+ H2O
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8. Determine the structure of the following compound based on the 1H-NMR spectrum and IR data given. Put your final structure in the box. (show work for partial credit). (6 pts) C7H13O2Cl
IR: 1740 cm-1 1H-NMR: 1.29 ppm (t, 3H); 1.60 ppm (d, 3H); 1.92 ppm (q, 2H); 2.35 ppm (t, 2H); 3.64 ppm (sextet, 1H); 4.13 ppm (q, 2H).
012345
PPM
3
1
2 22
3
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9. Provide the major product or the reaction conditions for the following reactions. (32 pts, 2 pts each box)
a.
b.
c.
d.
f.
e.
H
1. O32. Zn, CH3COOH
CrO3H2SO4, H2O
Name the reaction for 2 bonus points
H HgSO4H3O
+
Name the reaction for 2 bonus points
NH2NH2 KOH, heat
O O
Cl
1. NaCN
2. H3O+
3. BH34. H3O
+
NH2
O 1. SOCl2, heat
2. H3O+, heat
3. SOCl2
HO OH
O O
1. heat
2. CH3OH
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h.
i.
j.
k.
g.
O
O
O
H
O
Name the reaction for 2 bonus points
O
NH
NH2 , H+
, H+
Name the functional group for 2 bonus
points
O
Cl
POCl3, pyr
OH
O HN
H+
CH3OH (xs)
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10. Provide a reasonable synthesis for the following molecules using the given starting material and anything else with 3-Carbon atoms or less. Several steps are required. (Show work for partial credit) (18 pts, 6 pts each) a.
Br
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b.
OH
O
O
H
O
N
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c. (Hint: You should use your starting material to make BOTH parts that form the product).
Br
HN
O
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Scratch Sheet: Needs to be turned in with the test (if missing, the test will not be graded)
