Question

Acetyl chloride does not react with
(A) Di-ethyl ether
(B) Aniline
(C) Phenol
(D) Ethanol

Answer 1

Hint : Ethanol reacts with acetyl chloride to form Ethyl acetate which is an ester. This process is called Desertification. The reaction of aniline with acetyl chloride which inturn forms the Acetanilide. Di-ethyl-ether reacts with acetyl chloride to form esters and haloalkanes.

Complete Step By Step Answer:
The reaction of ethanol with acetyl chloride
${{C}_{2}}{{H}_{5}}OH+C{{H}_{3}}COCl\to C{{H}_{3}}CO{{C}_{2}}{{H}_{5}}$
Ethanol reacts with acetyl chloride to form esters. The formation of ester is known as Desertification. Since the product is formed, the answer is not Option D. The reaction of acetyl chloride with Di-ethyl ether. ${{C}_{6}}{{H}_{5}}N{{H}_{2}}+C{{H}_{3}}COCl\to {{C}_{8}}{{H}_{9}}NO+HCl$
Di-ethyl-ether reacts with acetyl chloride to form Esters and Haloalkanes. Since the product is formed, the answer is not Option A.
The reaction of acetyl chloride and aniline ${{C}_{6}}{{H}_{5}}N{{H}_{2}}+C{{H}_{3}}COCl\to {{C}_{8}}{{H}_{9}}NO+HCl$. Aniline reacts with acetyl chloride to form acetanilide
Since the product is formed, the answer is not Option B.
The reaction between phenol and acetyl chloride. Phenol does not react directly with acetyl chloride. At first, phenol reacts with sodium hydroxide to form sodium phenoxide. Further sodium phenoxide reacts with acetyl chloride to form phenyl acetate. Acetyl chloride is the strongest acetylating agent which has the strongest acetylating property. Phenols have stronger boiling points, hydrogen bonding, and are easily soluble. Phenol, as a mild acid, does not have the capability to react with carboxylic acids. Carboxylic acid groups are more acidic compared to phenol. Therefore, sodium groups interact in between them as a weak base thereby helping the phenols to react further.
Therefore, the answer is option C.

Note :
Phenol does not react directly with acetyl chloride. Phenol reacts with sodium hydroxide first to form sodium phenoxide. Further sodium phenoxide reacts with acetyl chloride to form phenyl acetate.