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Q.Aspirin is obtained by acetylation of (A) Phenol (B) Salicylaldehyde (C) 2-Hydroxybenzoic acid (D) Benzoic acid

CBSECBSE Class XII Board 2026MCQ· 1mImportance★★★★★
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Aspirin (acetylsalicylic acid) is synthesized by acetylating the phenolic –OH group of salicylic acid (2-hydroxybenzoic acid) with acetic anhydride. The answer is (C).

Aspirin is one of the most widely used drugs in the world, and understanding its synthesis reveals why the starting material must have both a carboxylic acid group and a phenolic hydroxyl group in the right positions.

The acetylation reaction replaces an active hydrogen (typically on an –OH or –NH₂ group) with an acetyl group, −COCHX3\ce{-COCH3}. When we acetylate a phenol, we convert Ar−OH\ce{Ar-OH} into Ar−O−CO−CHX3\ce{Ar-O-CO-CH3}, forming an ester. The key is identifying which compound has the structural features needed to become aspirin.

Aspirin's structure is 2-acetoxybenzoic acid: a benzene ring with a carboxylic acid group at position 1 and an acetoxy ester group (from acetylation) at position 2. Working backward, the precursor must have a carboxylic acid at position 1 and a free hydroxyl group at position 2.

Let me examine each option:

  1. Phenol (CX6HX5OH\ce{C6H5OH}) has only a hydroxyl group attached to benzene, with no carboxylic acid. Acetylating phenol gives phenyl acetate, not aspirin.

  2. Salicylaldehyde has an aldehyde group (−CHO\ce{-CHO}) at position 1 and a hydroxyl at position 2. While acetylation would modify the –OH, the aldehyde is not a carboxylic acid, so this cannot yield aspirin.

  3. 2-Hydroxybenzoic acid (salicylic acid) has a carboxylic acid (−COOH\ce{-COOH}) at position 1 and a phenolic hydroxyl (−OH\ce{-OH}) at position 2. When treated with acetic anhydride or acetyl chloride, the –OH undergoes acetylation:

CX6HX4(OH)(COOH)+(CHX3CO)X2O→CX6HX4(OCOCHX3)(COOH)+CHX3COOH\ce{C6H4(OH)(COOH) + (CH3CO)2O -> C6H4(OCOCH3)(COOH) + CH3COOH}

This produces acetylsalicylic acid—aspirin. …

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