CHAPTER 19: CARBOXYLIC ACID DERIVATIVES

19.5 ACYL CHLORIDE

1. IUPAC NAMING

Propanoyl chloride
Ethanoyl chloride

Hexanoyl chloride
Butanoyl chloride

Phenylethanoyl
Benzoyl chlorede chloride

2. Preparation of acyl chloride

Reagent:

Condition:

Equation:

3. Chemical reactions of acyl chloride

A. Hydrolysis of acyl chloride

Reagent:

Condition:

Equation: (white fume of HCl produce)

O

H3C C Cl

O
H3C CH C Cl
CH3

Cl
B. Esterification of acyl chloride

Reagent

Condition
O

H3C C Cl

O
H3C CH C Cl
CH3

Phenyl benzoate is prepared by reacting benzoyl chloride and phenol in alkaline solution under reflux

Reagent:

Condition:

Equation:
O

Cl

C: Formation of amide

Reagent: ammonia, NH3

Condition:

Equation
O

H3C C Cl

O
H3C CH C Cl
CH3

Cl
Reagent: primary amine

Condition:

Equation
O

H3C C Cl

O
H3C CH C Cl
CH3

Reagent: secondary amine

Condition:

Equation
O

H3C C Cl

O
H3C CH C Cl
CH3

19.6 ESTER

1. IUPAC NAMING

Methyl etanoate Ethyl propanoate

Ethyl etanoate Cyclopenthyl

methanoate

Prophyl benzoate Phenyl benzoate

2. Preparation of ester

Reagent

Condition

Equation
O
H3C CH C OH
CH3

O
H3C CH C Cl
CH3

3. Chemical reactions of Ester

A. Hydrolysis of Ester

Reagent:

Condition:

Equation
O
H3C CH C O CH2 CH3
CH3

O
CH3
O

Reagent:

Condition:

Equation:

O
H3C CH C O CH2 CH3
CH3

O
CH3
O
B. Reduction of Ester

Reagent:

Condition:
O
CH3
O

O
H3C CH C O CH2 CH3
CH3

Natural Ester formed from Propan – 1,2,3 triol ( glycerol) and long fatty chain

19.7 Amide

1. IUPAC NAMING

Primary amide Secondary amide

ethanamide
N-phenylbenzamide

Primary amide Tertiary amide

Benzamide N- ethyl-N-methylpropanamide

Tertiary amide
Secondary amide N-methy- N-phenylbenzamide

N-methylpropanamide

2. Preparation of Amide

Reagent:

Condition:
O

H3C C OH
 O

H3C C Cl

H3C C Cl

H3C C Cl

3. Chemical Reaction of Amide

A. Hydrolysis of Amide

a) Reagent:

Condition:
O

H3C C NH2

H3C CH2 C NH CH3

NH CH3

H3C C N CH3
CH3

b. Reagent

Condition
O

H3C CH2 C NH CH3

NH CH3
c. Reagent

Condition
O

NH CH3

H3C CH2 C NH CH3

B. Reduction of Amide

Reagent

Condition
O

H3C CH2 C NH CH3

H3C CH2 C NH CH3

C. Dehydration of amide

Reagent:

Condition
O

H3C C NH2

D. Reaction with nitrous acid, HNO2 (insitu preparation – sodium nitrite (NaNO2) and conc HCl in cold condition (0-
5oC

Reagent

Condition
O

H3C C NH2

O
H3C CH2 C NH2