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JIPMER2014ChemistryCarboxylic Acid Derivatives

The relative reactivities of acyl compounds towards nucleophilic substitution are in the order of

Options

  1. Aacyl chloride acid anhydride ester amide
  2. Bester acyl chloride amide acid anhydride
  3. Cacid anhydride amide ester acyl chloride
  4. Dacyl chloride ester acid anhydride amide

Correct answer

A. acyl chloride acid anhydride ester amide

Step-by-step solution

The ease of nucleophilic substitution is depend upon the nature of leaving group. When the leaving tendency of a group in a compound is high, then the compound is more reactive towards nucleophilic substitution. The nucleophilic acyl substitution is completed in two steps as shown below The reactivity of the compound may be explained on the basicity of the leaving group. A weaker base is a better leaving group. The basicity order is as Cl ⁻ RCOO ⁻ RO ⁻ NH ₂⁻ Hence, the order of the leaving tendency is Cl ⁻ RCOO ⁻ R

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