Post on 28-Dec-2015
Chlorination of Acetylene
- Study of carbon and carbon compounds
- Carbon forms covalent bonds ( e neg diff < 1.7) with many other atoms
- Huge chains of C to C bonds, rings, networks
-petroleum, coal, wood, animals, other plant products
Characteristics of Organic Compounds Characteristics of Organic Compounds ( covalent ( covalent substances )substances )
1. Low M.P. and B.P. (have weak intermolecular forces)
2. Nonconductors ( e- are not free to move around)
3. Nonpolar therefore won’t dissolve in polar substances like water - only dissolve in other nonpolars
- - Like Dissolves LikeLike Dissolves Like
4. React Slowly ( bonds between atoms are relatively strong )
- Are nonelectrolytes
- Exception organic acids (CH3COOH)
- Usually exist as gases, liquids or low m.p. solids
Types of BondsTypes of Bonds
1. Carbon has 4 valence electrons : can form 4 covlent bonds
CC2. Two carbons can form a covalent bond; single bond- One pair of shared electrons
- If all bonds between carbons are single the molecule is called saturatedsaturated
CC CC
3. If two pairs of electrons are shared between carbon atoms, double bond results
-organic compounds with double or triple bonds are said to be unsaturatedunsaturated
CC CC4. If three pairs of electrons are shared a triple bond is formed
CC CC
Molecular Formula- Shows number and type of elements in a compound
Ex. CH4
Structural Formula -shows elements and the arrangement of atoms
HH C H H
- Each line represents a pair of shared electrons
Isomers - Compounds with the same molecular molecular formulaformula but different structural formulastructural formula
- All have molecular formula C6H14
- Have different properties
HydrocarbonsHydrocarbons
- Contain only C and H
- Names are based upon longest carbon chain
- Organized into homologous series
- As molecular size increases the b.p. and f.p increase due to stronger intermolecular forces
- Members increase by one C and some H’s
Alkanes Alkanes Table QTable Q
- A homologous series of saturatedsaturated hydrocarbons
C C CCC
-all single covalent bonds
- Have the general formula CnH2n + 2 Table QTable Q
- Named according to the IUPAC system of nomenclature
- Prefix – denotes number of carbon atoms
Meth 1 carbon atom
Eth 2 carbon atoms
Prop 3 carbon atoms
but 4 carbon atoms
pent
5 carbons
Table P has all the prefixes you’ll need to Table P has all the prefixes you’ll need to know!!!know!!!
Alkanes always end in name –ane Table QTable Q
H - - H
H |
H |
H |
H |
H |
H |
H |
H |
H |
H |
H - - H
H |
H |
H |
H |
H |
H |
H |
H |
H - - H
H |
H |
H |
H |
H |
H |
H - - H
H |
H |
H |
H |
2. Naming alkanes
# of prefix alkane Structural formula molecular formula carbons
1.
2.
3.
4.
5.
meth methane
but
prop
eth
pent
ethane
propane
butane
pentane
CH4
C2H6
C4H10
C3H8
C5H12
HH C H H
C-- C
C--C --C
C--C --C --C
C--C --C -- C-- C
All end in “ane”. The prefix indicates the number of carbons in the longest chain
- Butane is the first alkane that can exist as an isomer
-As the number of C in the molecule increases the number of isomers also increases
Isomers of pentane
Alkyl Groups - An alkane with one less H CnH2n + 1
- Are side groups on longer chains
- End in - yl
CH3 – methyl group
C2H5 – ethyl group
IUPAC System for Naming Alkanes
1. Use ane ending
2. Attach prefix to show number of carbon atoms in longest chain
| | | |- C - C - C - C - | | | | |
- C - |
| - C - |
A.hexane | | | |
- C - C - C - C - | | | |
| - C - |
| - C - |
| - C - |
B.
hexane | | | |- C - C - C - C - | | | |
| - C - | |
- C - |
| - C - | |
- C - | | - C - |
C.
heptane
3. If there are side branches, number the parent chain from which end reaches the branch soonest H
|H- CHH H H | | | |H - C - C - C - C - H | | | | H H HCH H | H
4. Determine name for each branch5. Write the complete name for the compound. Place a number in front of side chain to indicate where it occurs on parent chain.
H H H H H H | | | | | |H - C - C - C - C - C - C - H | | | | | | H HHCH H H H | H - C - H | H
2-methyl pentane
3-ethyl hexane
6. If there are two or more identical alkyl groups use prefixes: di (2); tri (3) ; tetra (4). Use numbers seperated by commas to identify the location of the groups.
CH3 CH CH CH3
CH3
CH3
2,3 – dimethylbutane
Practice - Name the following hydrocarbons
H |H- CHH H H H H | | | | | |H - C - C - C - C - C- C -H | | | | | | H HHCHH H H | H
H | HHCH H H H H | | | | | |H - C - C - C - C - C - C - H | | | | | | H HHCH H H H | H
H | H H HCH H H H | | | | | |H - C - C - C - C - C - C - H | | | | | | H H HCH H H H | H-C-H | H
H H H H H H H H | | | | | | | |H - C - C - C - C - C - C - C - C - H | | | | | | | | H H HHCH H H HCH H | | HCH H | HCH | H
a. b.
c.d.
heptane
hexane octane
hexane4-methyl 2,3- dimethyl
3-ethyl 3-methyl 2-methyl 5-propyl
Practice - Name the following compounds.
A.
B.
C.
CH3
| CH2 - CH2 - CH - CH2 - CH3
| CH3
CH3
|CH3 - CH2 - C - CH2 - CH3
| CH3
CH3 – CH2 - CH2 - CH - CH2 - CH2 - CH3
| CH2
| CH2
| CH3
3- methyl hexane
3,3- dimethyl pentane
4-propyl heptane
AlkenesAlkenes- A homologous series of unsaturatedunsaturated hydrocarbons containing ONE double bond CnH2n- To name change end of alkane to eneene
- Hydrocarbons with more than 1 double bond are not alkenes
Name Formula Structure
Ethene C2H4
Propene C3H6
Butene C4H8
AlkynesAlkynes - Homologous series of unsaturated hydrocarbons containing ONE triple bond CnH2n-2
- To name change ane ending to -yneyne
Other Organic CompoundsOther Organic Compounds
- Occur when one or more H’s are replaced by other elements- Are usually named from corresponding hydrocarbon
Functional Group -Functional Group -A particular arrangement of a few atoms, giving characteristic properties to an organic molecule
Ex. - OH alcohols- COOH organic acids
- CHO aldehydes
Halides - Normal alkanes with group 17 element substituted in for a H
H Br | |H - C - C - H | | H H
1-bromoethane
Naming substituted alkanesNaming substituted alkanes
a. The longest chain of carbon atoms is the base name
Cl H | |H - C - C - H H H H
| | | | | H H-C - C - C - C - H
| | | | H H H H
This has six carbons in the longest chain, so it is some form of
Hexane
b. Write the halogen group name before the base name
Cl Br F IChloro Bromo Fluoro Iodo
c. Name the location of the extra group
Since the chlorine is on the first carbon, it is
1-chloro
HexaneChloro1-
Important pointImportant pointImportant pointImportant point
The hydrocarbon chain is numbered so that the extra groups have the lowest number possible
Start numbering the chain on the side closest to the extra group
H H
| |H - C - C - H H H H
| | | | | H H-C - C - C - C - H
| | | | H H Cl H
124
56This is 2-chloro hexane, not 5-chloro hexane
3
Name these compounds
They are actually the same, one is just flipped over.
H H | |H - C - C - Br | | H H
H H | |Br- C - C - H | | H H
2-bromo ethane1-bromo ethane
H H | |H - C - C - Br | | H H
H H
| |
H - C
- C - Br
| |
H H
H H
| |
H - C
- C - B
r
| |
H H
H H
| |H
- C - C
- Br
| | H
H H H
| |
H - C - C - Br
| |
H H H H | |Br- C - C - H | | H H
To avoid this
Examples - Name the following
H Cl H H
| | | | H-C - C - C - C - H
| | | | H H H H
H H
| |H - C - C - H H H
| | | | H H-C - C - C - H | | | Br H H
I H | |H - C - C - H | | H H
a. b. c.
butanechloro2- pentanebromo3-
ethaneiodo1-
d. If a group appears more than once, we number both places and add di tri tetra to the halogen prefix
2 3 4 H H
| |H - C - C - H Cl H H
| | | | | H H-C - C - C - C - H
| | | | H H Cl H
This hexane has a chlorine on carbons #2 and #3
Called 2,3 - dichloro hexane
Examples - Name the following Cl Cl H H
| | | | H-C - C - C - C - H
| | | | H H H H
H H
| |H - C - C- H Br H
| | | | H H-C - C - C - H | | | Br Br H
I H | |H - C - C - H | | H I
a. b. c.
butanedichloro1,2-pentanetribromo2,2,3-
ethanediiodo1,2-
e. When different halogens are added, alphabetize the prefix names
Cl Br | |H - C - C - H H H H
| | | | | H H-C - C - C - C - H
| | | | H H H H
This has a Chlorine on #1 and a Bromine on #2, so bromine comes first
hexane2-bromo, 1-chloro
Examples - Name the following Cl F H H
| | | | H-C - C - C - C - H
| | | | H H H H
H H
| |I - C - C- H Br H
| | | | Cl H-C - C - C - H | | | Br Br H
I H | |H - C - C - H | | Cl I
a. b. c.
butane2-fluoro1 chloro
pentane1-chloro3,4,4-tribromo
ethane1,2-diiodo1-chloro
1-iodo
AlcoholAlcohols s
- One or more H’s have been replaced with OH group- Only one OH per carbon
-Alcohols are NOT bases OH does not form hydroxide ions in solution
-Are classified by:
1.) Number of –OH groups in molecule2.) Number of C chains attached to C that has the –OH on it
- When writing molecular formulas, the OH is written last
C2 H5 OHThe OH on the end indicates that it is an alcohol
H H | |H-C--C--OH | | H H
H O | |-C--C--OH | |
Example - Write out the molecular formula of the alcohols H |H-C--OH | H
H O H H | | |H-C--C--C--H | | | H H H
H | HCH H H | | |H-C--C--C--OH | | | H H HCH3
H9
H7 C4
C3
OHOH
OHNaming Alcohols
Replace the “e” of the alkane name with“ol”
We will only be looking at alcohols with single bondsWe will only be looking at alcohols with single bonds
H |H-C--OH | H
Name Common name
methane
Methyl alcohol Wood alcoholVery poisonousused as a laquer thinner
ol
H H | |H-C--C--OH | | H H
ethanol Ethyl alcohol Mild poison (large doses kill)Used in liquor, medicine
Monohydroxy alcohols - Have only one OH group
Primary alcohols – the OH is attached to an end carbon
H H H | | |H-C--C--C--OH | | | H H H
H H | |H-C--C--OH | | H H
No special naming rules
propanol ethanol
Secondary Alcohol -OH is in the middle of a chainCarbon holding the OH has two other carbons attached to it
H H O H H | | | |H-C--C--C--C--H | | | | H H H H
H H H H H H | | | | | |H-C--C--C--C--C--C--H | | | | | | H H H H O H H
Must number the carbon chain and name the location of the OH
butanol2- hexanol2-
Examples - Name the following alcohols
Br H H H H | | | | |H-C--C--C--C--C--H | | | | | H H H O H H
H | H H HCH H
| | | |H--C--C--C--C--OH | | | | H H H H
Butanol2-methylPentanol2-5-bromo
The carbon chain is numbered for the functional group
Dihydroxy alcohols
Have two hydroxyl groups
Named by adding “diol” to the alkane name. (keep the “e”)Must name the location of both alcohol groups
H H | |H-C--C--H | | O O H H
ethanediol1,2-Commonly called ethylene glycolCommon component of antifreeze
Written as C2H4(OH)2
EXTRA
Trihydroxy alcohols
Have three OH groups attachedAdd “triol” instead of “diol”
H |H-C-OH |H-C-OH |H-C-OH | H
called1,2,3-propanetriolCommonly calledGlycerine or GlycerolUsed in fat production
Practice - Name the following alcohols H |H-C-OH |H-C-H |H-C-OH | H
H |H-C-Br |H-C-OH |H-C-OH | H
Br H H H H | | | | |H-C--C--C--C--C--H | | | | | H O O H O H H H
1,3-propanediol
3-bromo 1,2 propanediol
5-bromo 1,3,4-pentanetriol
Written as C3H5(OH)3
Organic AcidsOrganic Acids-the functional group is the carboxyl group
O ||--C--OH
In solution, it is the H from the OH that is creates the H+
Always written as “COOH” at the end of the molecular formula
H H H O | | l ||H-C--C--C--C--OH | | | H H H
C3H7COOHThis is how you recognize an organic acid
R - COOH
Practice - Write out the molecular formula for the following
H H O | | ||H-C--C--C--OH | | H H
O ||H--C--OH
O H || |HO-C--C--H | H
C2H5COOH HCOOH CH3COOH
Naming Organic Acids
Take the longest alkane chain, remove the “e” and add “oic acid”
O ||H--C--OH
Methanoic acid Commonly called Formic acid
H O l ||H-C--C--OH | H
Ethanoic acid Commonly called Acetic acid
Example - Name the following acids
H H O | | ||H-C--C--C--OH | | H H
H H O | | ||H-C--C--C--OH | | HCHH | H
O H H H H || | | | |HO-C--C--C--C--C--H | | | | H H Cl H
Propanoic acid Butanoic acid Pentanoic acid4,4-dichloro
Aldehydes
Functional group O ||-C-H
Naming- remove the “e” from the alkane and adding “al”
Solvents, embalming
R-CHO
Structural Formula
Name
Common Name
Uses
Molecular formula
O ||H--C--H
H O | ||H--C--C--H | H
O H H || | |H--C--C--C--H | | H F
methanal
formaldehyde
Preserving fluidirritating to lungs
CH2O
ethanal
acetaldehyde
Used to makesynthetic rubber
C2H4O
3-fluoro propanal
C3H4OF
Ketones
Functional group
Must have at least one carbon on either side
Naming - remove the “e” from the alkane and adding “one”
O ||--C--
Double bonded oxygen is in the middle of a chain
Solvents manufacturing of plastics
Structural Formula
Name
Common Name
Uses
Molecular formula
H O H | || |H--C--C--C--H | | H H
H H O H | | || |H--C--C--C--C--H | | | H H H
H O H H H | || | | |H--C--C--C--C--C--H | | | | H H Cl H
propanone
Acetone
Nail polish remover
CH3COCH3
2-butanone
CH3COC2H5 CH3COC3H6Cl
4-chloro 2-pentanone
Functional group
Must have at least one carbon on either side
Naming - alphabetize the two groups on either side of the --O--, then add the word “ether”
Molecular formula - Starting with the shorter side,write everything before the --O--, then write “O”, then write everything after
Ethers--O--
Anesthietics
Structural Formula
Name
Common Name
Uses
Molecular formula
H H | | H--C--O--C--H | | H H
H H H H H | | | | |H--C--C--C--O--C--C--H | | | | | H H H H H
Dimethyl ether
CH3OCH3 C2H5OC3H7
Ethyl propyl ether
Amine
Functional group
Naming- remove the “e” from the alkane and adding “amine”
Methanamine, propanamine
H |--N--H
Amino acids, manufacture of plastics, dyes H |--N--
Structural Formula
Name
Molecular formula
H H H | | |H--C--C--N--H | | H H
H H H H | | | |H--N--C--C--C--H | | | H H H
ethanamine
C2H5NH2
propanamine
C3H7NH2
Special compounds Amino Acids
Contains an amine group and an acid group attached to a carbon
H |H – N -
H |C |R
O ||- C – OH
amine Carboxyl (acid)
The “R” can be any atom or group of atoms.
Basic building blocks of all proteins in the body.
When amino acids combine, they form an AMIDE
H |H – N -
H |C |R
O ||- C – OH
H |H – N -
H |C |R
O ||- C – OH
H2O
H |H – N -
H |C |R
O ||- C –
H | N -
H |C |R
O ||- C – OH
Amide
Functional group
Naming - remove the “e” from the alkane and adding “amide”
O H || |- C--N--H
Proteins, medicines
Structural Formula
Name
Molecular formula
H O H | || |H--C--C--N--H | H
H O H H | || | |H--N--C--C--C--H | | H H
ethanamide
CH3CONH2
propanamide
C2H5CONH2
O H || |- C--N--
Generally,organic reactions occur slower than inorganic reactions
Many reactions require a catalyst to lower the activation energy
Substitution Reaction
Halogen gas + saturated hydrocarbon
One atom in the halogen gas switches places with one of the hydrogens in the hydrocarbon (halogenation)
Creates a substituted hydrocarbon and an acid
H H H | | |H--C--C--C--H | | | H H H
Br - Br
BrBr
HH
BrHBr
H
- Replace one kind of atom or group with another
If a second halogen gas is added, another substitution will occur
If we repeat this process 4 times with chlorine and methane, we get
If we take methane and do 2 chlorine substitutions and 2 fluorine substitutions, we get
Carbon tetrachloride
Dichloro difluoromethane
Freon
H H H | | |H--C--C--C--H | | | H H H
H Br H | | |H--C--C--C--H | | | H H H
H Br H | | |H--C--C--C--Cl | | | H H H
+ Br2-->
HBr
+ Cl2 -->
HCl
H |H--C--H | H
+ 4 Cl2
Cl |Cl--C--Cl | Cl
+ 4 HCl
H |H--C--H | H
+ 2 Cl2
+2 F2
Cl |F--C--F | Cl
+ 2 HCl and 2 HF
Addition ReactionHalogen + Unsaturated hydrocarbon
- When the double bond breaks, we have two open bonding sites
Both of the halogen atoms are added
H H | |H--C--C C--C--H | | | | H H H H
F--FFFFFF
FFF
F
We only have one product!We only have one product!
- Usually involves adding one or more atoms at a double or triple bond- Resulting molecule is saturated
Don’t Write whats next!!!
“Hydrogenation” H H H | | /H--C--C==C | \ H H
+ H2 -->
H H H | | |H--C--C--C--H | | | H H H
H H H | | |H--C--C==C--C--H | | | H H H
+ Br2
H H Br H | | | |H--C--C--C--C--H | | | | H Br H H
2,3-dibromobutane
Fermentation
- Glucose is broken down by enzymes to make alcohol and carbon dioxide
C6H12O6
zymase2 C2H5OH + 2 CO2
glucoseenzyme
ethanol
Notice how the OH from acid and H from alcohol are removed
This is a type of Dehydration Synthesis
Removal of water to create a bond
EstersEsters
Functional Group
In a molecular formula, written as
EsterificationOrganic acid + alcohol --> ester + water
H H O | | ||H--C--C--C--OH | | H H
H H H | | |HO--C--C--C--H | | | H H H
H H H | | | O--C--C--C--H | | | H H H
H H H | | |HO--C--C--C--H | | | H H H
H H H | | | O--C--C--C--H | | | H H H
H H H | | | O--C--C--C--H | | | H H H
H2O
O ||--C--O--
COO
This will appear in the middle of a formula
- Fruity odor
Named by taking the groups name of the alcohol, then by taking the “oic acid” and changing it to “oate”
Examples
H H O | | ||H--C--C--C-- | | H H
H H H | | | O--C--C--C--H | | | H H H
Acid side Alcohol side
C2H5 COOC3H7
H H O | | ||H--C--C--C-- | | H H
H H | | O--C--C--H | | H H
Ethanol
Ethyl
Propanoic acid
propanoate
H O | || H--C--C-- | H
H H H | | | O--C--C--C--H | | | H H H
Propyl ethanoate
Examples - Write out the products of the esterification, then write the molecular formula of the ester
O || H--C--OH
H H H H | | | |HO--C--C--C--C--H | | | | H H H H
O H || | HO--C--C--H | H
H H H O | | | H--C--C--C--H | | | H H H
O || H--C--
H H H H | | | | O--C--C--C--C--H | | | | H H H H
H O | || H--C--C-- | H
H H H | | | O--C--C--C--H | | | H H H
Butyl methanoate
Propyl ethanoate
+ H2O
SaponificatioSaponificationn - Hydrolysis of an ester in presence of a fat to make
soap
Combustion (oxidation)Combustion (oxidation)
- With excess oxygen; hydrocarbons burn completely to form carbon dioxide and water
CH4 + 2 O2 CO2 + 2 H2O
Polymerization
- The formation of a larger molecule from a smaller onePolymer - Chains of small units bonded together
Natural Polymers – starch, cellulose, proteins
Synthetic Polymers – nylon, polyethylene ( plastic)