The most reactive of the carboxylic acid derivatives towards nucleophilic attack is

Correct answer: D. the acyl chloride

  • A. the amide
  • B. the ester
  • C. the carboxylate salt
  • D. the acyl chloride

Explanation

Chlorine is a good leaving group and withdraws electron density strongly, so the carbonyl carbon of an acyl chloride is highly electron deficient and it reacts violently even with cold water. Reactivity falls in the order acyl chloride, anhydride, ester, amide, since each successive group donates electron density more effectively. This is why acyl chlorides are the reagents of choice for making esters of unreactive alcohols and phenols.

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About Carboxylic Acid Derivatives

Carboxylic acid derivatives include acid halides, acid anhydrides, esters and amides, formed by replacing the hydroxyl group of a carboxylic acid. Their nomenclature, structures, preparation, hydrolysis and relative reactivity are linked through nucleophilic acyl substitution, which differs from the nucleophilic addition reactions of aldehydes and ketones.

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550 free Carboxylic Acids MCQs from Chemistry, each with the correct answer and an explanation. Unlimited attempts, no account needed.

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