CARBOXYLIC ACIDS AND

ESTERS
PREPARED BY
SYED ABDUL ILLAH ALYAHYA
UNIVERSITI TEKNOLOGI MARA
PUNCAK ALAM CAMPUS

CARBOXYLIC ACIDS AND

ESTERS

Carboxylic Acids
Nomenclature of Carboxylic Acids
Reactions of Carboxylic Acids
Esters
Nomenclature of Esters
Hydrolysis and Reduction of Esters

Carboxylic Acids

CnH2n + 1COOH

(n 0)

RCOOH
Sour tasting

Weak acids
Citric acid
found in citrus fruit

Ethanoic acid = acetic acid, CH3COOH

vinegar

Methanoic acid = formic acid, HCOOH

insect bites and stings

Carboxylic Acids
Preparation of Carboxylic Acids
Made by the oxidation of aldehydes and primary alcohols
O
CH2OH

C
[O]

Benzyl alcohol

Benzoic acid

C
H

Benzaldehyde

OH

[O]

C
OH

Benzoic acid

Nomenclature of Carboxylic
Acids
Carboxylic acid group always on end of main chain
has highest naming precedence of functional
groups
C of group always C1
position not indicated in name
Change ending to oic acid

O
CH3CH2CH2CH2CH2C OH
6

Hexanoic acid or caproic acid

which causes foot odor

Nomenclature of Carboxylic
Acids
CH2CH3 O
3

CH3CH2CHCHCH2C OH
6

Cl

CH3 O
3

CH3CH2CH2CCH2C OH
6

OH

3-chloro-4-ethylhexanoic acid

3-hydroxy-3-methylhexanoic acid

COOH

C OH

3
2

3-cyclohexylbutanoic acid

cyclopentanecarboxylic acid

Reactions of Carboxylic Acids

Neutralisation: Reactions with bases to form salts of
the acids and water.
CH3COOH + NaOH CH3COONa + H2O

Reactions with Reactive Metals : forming salts of the

acids and H2 gas
2CH3COOH + 2Na 2CH3COONa + H2
Reactions with hydrogen carbonates: forming salts of
the acids, CO2 and H2O
CH3COOH + NaHCO3 CH3COONa + CO2 + H2O

Reactions of Carboxylic Acids

Reductions of Carboxylic Acids
Carboxylic acids are reduced by very strong
reducing agents such as lithium aluminum hydride in
ether, producing primary alcohols.
CH3COOH

LiAlH4/ether

CH3CH2OH + H2O

Reactions of Carboxylic Acids

Esterification
When a carboxylic acid is heated with an alcohol in the
presence of concentrated sulphuric acid as catalyst, an
ester is produced.
RCOOH + ROH

conc. H2SO4

RCOOR + H2O

Example:
CH3CH2COOH + CH3OH
propanoic acid

methanol

conc. H2SO4

CH3CH2COOCH3 + H2O

methylpropanoate

Esters
RCOOR
Sweet odor
Made by reacting carboxylic acid with an alcohol in the
presence of conc. sulphuric acid as catalyst
RCOOH + ROH conc. H2SO4
RCOOR + H2O

Nomenclature of Esters
Carboxylic acid group always on end of main chain
unless carboxylic acid group present
C of ester group on C1
position not indicated in name
Begin name with alkyl group attached to O
Name main chain with oate ending

Nomenclature of Esters
3-methylbutyl acetate
CH3

H3C
4

CH
3

Isopropyl pentanoate

O
H2
C
1
O

2
C
H2

C
2

O
1
CH3

1
H2 C

2
C
H2

H2
C
3

O
H3C
1

2
C
H2

C
3

4
C
H2

C
5

CH3

CH
2

CH3
1

O
O

H2
C
1

2
C
H2

H2
C
3

CH3
4

Butyl propanoate

Group in pink circle is carboxylate

Group in blue square is alkyl

H3 C

2
CH
CH3
1

C
3

H2
C
1

2
C
H2

Butyl isobutyrate

H2
C
3

CH3
4

Hydrolysis and Reduction of

Esters
Hydrolysis of esters is the reverse of esterification
Acid Hydrolysis of an ester in the presence of dilute
HCl or dilute sulphuric acid produces an alcohol and a
carboxylic acid
If an alkali is used instead of an acid, the carboxylic
acid formed will be converted to the salt
CH3CH2COOCH3 + H2SO4

reflux

methylpropanoate

CH3CH2COOCH3 + NaOH
methylpropanoate

CH3CH2COOH + CH3OH
propanoic acid

reflux

methanol

CH3CH2COONa + CH3OH
sodium propanoate

methanol

Hydrolysis and Reduction of

Esters
Esters can be reduced to produce two alcohols by
strong reducing agent such as lithium aluminium
hydride (LiAlH4)
CH3CH2COOCH3
methylpropanoate

1. LiAlH4
2. H2O

CH3CH2CH2OH + CH3OH
propanol

methanol

AMINES
PREPARED BY
SYED ABDUL ILLAH ALYAHYA
UNIVERSITI TEKNOLOGI MARA
PUNCAK ALAM CAMPUS

AMINES
Amines
Hinsberg Test

Amines
Amines are organic derivatives of ammonia with one or
more alkyl or aryl groups bonded to nitrogen atom
Many are biological active
O

N
N
N
Nicotine

Cocaine

NH

HO

HO

NH2
Dopamine

H2N
Histamine

Amines
Biological Activity

Neurotransmitters: dopamine
Bioregulators: epinephrine
Vitamins: niacin, B6
Alkaloids: nicotine, morphine, cocaine
Amino acids

Amines
Classes of Amines
Primary (1): one C-N bond, 2
N-H bonds (RNH2).

CH3
H3CH2C C NH2
H
Butan-2-amine

Secondary (2): two C-N

bonds, 1 N-H bond (R2NH).

H
H3C C CH2CH3
H N CH2CH3
N-ethylbutan-2-amine

Amines
Classes of Amines
Tertiary (3): three C-N
bonds, no N-H bond
(R3N).

CH3CH2CH2CHCH2CH3
H3C N CH2CH3
N-ethyl-N-methylhexan-3-amine

Quaternary (4): four C-N

bonds, nitrogen has a +
formal charge.

CH2CH2CH3
H3C N+ CH2CH3
CH2CH3

Nomenclature of Amines
Primary amines are named in IUPAC system. Name
the alkyl or aryl groups bonded to nitrogen, then add
suffix -amine.
Name is based on longest carbon chain.
-e of alkane is replaced with -amine.
CH3

H2N

CH3 C NH2
CH3
1,1-Dimethylethylamine
or
tert-Butylamine

Cyclohexylamine

H2N
4,4-Dimethylcyclohexanamine

Nomenclature of Amines
Symmetrical secondary and tertiary amines are named
by adding the prefix di- or tri- to alky group
CH3
H3C N

CH2CH3
H3CH2C N

CH3
Trimethylamine

CH2CH3
Triethylamine

N
H
Diphenylamine

Nomenclature of Amines
Unsymmetrical substituted secondary and tertiary
amines are named as N-substituted primary amines
Largest alkyl group is chosen as the parent name, and
the other alkyl groups are N-substitutents on the parent
CH3

CH3
H3C

H
N

CH2CH2CH3
1

H3C

N-methylpropan-1-amine

CH

CH2CH3

CH2CH2CH2CH3
3

N-methylhexan-2-amine
CH3

CH2CH3
H3C

H
N

N-ethyl-N-methylcyclohexylamine

CH3CH2 N
CH2CH2CH2CH3
1

N-ethyl-N-methylbutan-1-amine

CH3
N,N-Dimethylpropylamine

H3C
N
H
N-methylcyclopentanamine

Nomenclature of Amines
Amine as Substituent
On a molecule with a higher priority functional group
the amine is named as a substituent. NH2 as an
amino
NH2
NH2
OH

CH3CH2CH2CHCH2CH2COOH
4-Aminoheptanoic acid

NH2
CH3
OHC
4-amino-4-methylcyclohexanecarbaldehyde

2-aminocyclopentanol

H3C

CH3

CH3CH2CH2CHCH2COOCH3
methyl 3-(dimethylamino)hexanoate

Nomenclature of Amines
Aromatic Amines
Amino group is bonded to a benzene ring. Parent
compound is called aniline.

NH2
NH2

H3C N CH3

CH3
Aniline

N,N-dimethylbenzenamine

4-Methylanaline
p-toluidine

Hinsberg Test
This test is used to distinguish between 1o, 2o and 3o
amines
This test is carried out by shaking a mixture of
benzenesulphonyl chloride and an amine in the
presence of excess NaOH solution, followed by addition
of HCl solution.

1o amine- a clear solution is formed on shaking and a

white precipitate is formed upon addition of acid
2o amine- a white precipitate is formed on shaking and
no changes upon addition of acid
3o amine no reaction