Lecture 67 Organic Chemistry III

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Lecture 67 - Organic Chemistry III
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Functional Groups

• an atom or group of atoms with a characteristic
  chemical behaviour
• regardless of the rest of the molecule

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1. Alcohols
-C-OH
CH3OH methanol CH3CH2OH ethanol
HO
OH
ethylene glycol
CC
H
H
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1. Alcohols
phenol
menthol
cholesterol
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Reactions of Alcohols
formation of ethers
CH3CH2-OH HO-CH2CH3
heat, H2SO4
CH3CH2 - O - CH2CH3

H2O
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2. Ethers

• general formula R - O - R

named for R, R
diethyl ether
CH3CH2 - O - CH2CH3
methyl t-butyl ether
O
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2. Ethers
low Tm, Tb
CH3CH2OCH2CH3
Tb 34oC
diethyl ether
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3. Aldehydes
H
general formula - C O
always occurs at end of chain
contains the carbonyl group
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Naming Aldehydes
O
O
O



C
C
C
H3C
H
H
H
H
benzaldehyde
resins, preservative
perfumes, flavors, plastics
artificial almond flavor
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Other Aldehydes
O
CHCH-C

CH3CH2CH2C
H
Butanal Butyraldehyde
Cinnamaldehyde
(Cinnamon)
(rancid butter)
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Other Aldehydes
O
1

CH3CHCH2C
H
Cl
3-chlorobutanal
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Making Aldehydes
oxidation of primary alcohols
H
oxidation
H3CC
CH3CH2OH

O
ethanol
acetaldehyde
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4. Ketones
O

C
general formula
R
R
ketones are named for R, R
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Naming Ketones
dimethyl ketone
C
CH3
H3C
propanone
2-
2
3
1
(acetone)
good solvent (nail polish remover)
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Naming Ketones
O

1
H3C-C-CH2CH2CH3
methyl propyl ketone
2-pentanone
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Other Ketones
OH
O
Testosterone
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Making Ketones
oxidation of secondary alcohols
H3CCHCH3
H3CCCH3
oxidation

OH
O
2-propanol
2-propanone
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Reactions of Ketones
Li
O
d-
d
OH
d-
d
H2O
H3CCCH3
CH3CH2CCH3
CH3CH2

CH3
ethyllithium
2 carbons
3 carbons
5 carbons
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5. Carboxylic Acids
OH
general formula
R-C

O
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Naming Carboxylic Acids
methanoic acid
HCOOH
(formic acid)
CH3CH2CH2COOH
butanoic acid
COOH
benzoic acid
octadecanoic acid
CH3(CH2)16COOH
(stearic acid)
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Reactions of Carboxylic Acids
carboxylic acid alcohol ester water
H3CC-OH H-OCH2CH3 H3CC-O-CH2CH3
H2O
an ester
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Reactions of Carboxylic Acids
Cl3CCOH HOCH3 Cl3CCOCH3 H2O
methanol
Less polar!
trichloroacetic acid
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6. Esters
R-C-O-R
general formula
named for R, R
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Naming Esters
O

H3C-C-O-R
acetate
O
ethyl acetate (nail polish remover)

H3C-C-O-CH2CH3
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Naming Esters
HO
butanoic acid (rancid butter)
ethyl butanoate (peachy pineapple)
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Naming Esters
HO
pentanoic acid (limburger cheese)
pentanol
pentyl pentanoate (apples)
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Other Esters
pentyl acetate
(bananas)
octyl acetate (oranges)
pentyl butyrate (apricots)
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Other Esters
ethyl formate
(rum)
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Lipids are Esters
e.g. dietary fats are triglycerides
O
Glycerol

CH3(CH2)16C
HO
CH2
OH
O

CH3(CH2)16C
HO
CH
OH
O

CH3(CH2)16C
HO
CH2
OH
Fatty acids
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Reactions of Esters
hydrolysis
HO-CH2
NaOH
HO-CH2

HO-CH2
a triglyceride
3 soaps
glycerol
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7. Amines
R3
general formula
N
R2
R1
N
N
N
R3
H
H
R1
R1
R1
R2
H
R2
primary
secondary
tertiary
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Naming Amines

• CH3NH2 methylamine
• (CH3)2N dimethylamine
• (CH3CH2)3N triethylamine

phenylamine (aminobenzene) (aniline)
NH2
diaminopropane (putrescine)
H2N(CH2)3NH3
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Other Amines
morphine, codeine, cocaine,
novacaine
O

C
NH2
HO
benzoic acid
amino
para
(PABA)