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IUPAC Naming of Acyl Chlorides

The document discusses carboxylic acid derivatives including acyl chlorides, esters, and amides. It provides their IUPAC naming conventions and describes methods of preparation and common reactions. Acyl chlorides can be prepared from carboxylic acids and undergo hydrolysis, esterification, and amide formation reactions. Esters are prepared from carboxylic acids and alcohols and react through hydrolysis and reduction. Amides form from reactions of acyl chlorides with ammonia or amines, and undergo hydrolysis, reduction, and reactions with nitrous acid.

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9 views7 pages

IUPAC Naming of Acyl Chlorides

The document discusses carboxylic acid derivatives including acyl chlorides, esters, and amides. It provides their IUPAC naming conventions and describes methods of preparation and common reactions. Acyl chlorides can be prepared from carboxylic acids and undergo hydrolysis, esterification, and amide formation reactions. Esters are prepared from carboxylic acids and alcohols and react through hydrolysis and reduction. Amides form from reactions of acyl chlorides with ammonia or amines, and undergo hydrolysis, reduction, and reactions with nitrous acid.

Uploaded by

sumathi
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd

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

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