MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Nucleophilic acyl substitution of carboxylic acid derivatives
JEE Advanced levelSingle correct optionDifficulty 3 of 3o1199

Ethyl 4-hydroxybenzoate is treated with a large excess of in dry ether: (i) (excess), dry ether; (ii) . The final product is

  1. A4-(propan-2-yl)phenol
  2. B4-hydroxybenzoic acid
  3. C1-(4-hydroxyphenyl)ethan-1-one
  4. D4-(2-hydroxypropan-2-yl)phenol

Answer: D

The phenolic OH consumes one equivalent of Grignard (giving methane and the phenoxide). The ester then adds two equivalents to give the tertiary alkoxide; the ketone stage is too reactive to stop. Acidic work-up gives the diol 4-(2-hydroxypropan-2-yl)phenol.
Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Nucleophilic acyl substitution of carboxylic acid derivatives

More questions on Nucleophilic acyl substitution of carboxylic acid derivatives