MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Nucleophilic acyl substitution of carboxylic acid derivatives
JEE Main levelSingle correct optionDifficulty 2 of 3o1185

Which alcohol undergoes Fischer esterification with acetic acid (acid catalyst, same conditions) at the highest rate?

  1. Aethanol
  2. B2-methylpropan-2-ol
  3. Cpropan-2-ol
  4. Dmethanol

Answer: D

The rate-determining attack of the alcohol oxygen on the protonated carbonyl carbon is sterically sensitive. Rate falls with increasing branching: methanol primary secondary tertiary, so methanol is fastest.
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