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Question
Acylation of amines with acyl halides proceeds by which of the following reaction?
Acylation of amines with acyl halides proceeds by which of the following reaction?
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Solution
The correct option is D nucleophilic substitution
The amines itself acts as nucleophiles and attack the acyl halide at the carbon-halogen bond to substitute the halogen atom by itself. This occurs by production of small amount of acid at each step, which may prevent the reaction by proceeding by protonating the amine.
The reaction is as follows:
RNH2+R′COCl→RNHCOR′+HCl
Here, R = Ph and R' = CH3
So, product formed will be PhNHCOCH3.
This is commonly known as acetanilide.
Hence, option (d) is correct.
General mechanism of this reaction follows 2 steps:
1) Attack of the nucleophile:
2) Removal of leaving group:
The amines itself acts as nucleophiles and attack the acyl halide at the carbon-halogen bond to substitute the halogen atom by itself. This occurs by production of small amount of acid at each step, which may prevent the reaction by proceeding by protonating the amine.
The reaction is as follows:
RNH2+R′COCl→RNHCOR′+HCl
Here, R = Ph and R' = CH3
So, product formed will be PhNHCOCH3.
This is commonly known as acetanilide.
Hence, option (d) is correct.
General mechanism of this reaction follows 2 steps:
1) Attack of the nucleophile:
2) Removal of leaving group:
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