The characteristic and important reaction of carboxylic acid derivatives is nucleophillic…

Chemistry · JEE Advanced · NTA ExamsCarboxylic Acids


The characteristic and important reaction of carboxylic acid derivatives is nucleophillic acyl substitution which is possible only when the incoming nucleophile (\(\mathrm{Nu}^{\odot}\) or \(\mathrm{HN}_{\mathrm{u}}\)) must not be a much weaker base than the group or substituent attached to the acyl group in the acid derivative. It is a two step process involving nucleophillic attack followed by the loss of the leaving group.
 
Arrange the following in the decreasing order of leaving group ability ?
(I) \(\mathrm{X}^{\ominus}\) (II) \(\stackrel{\ominus}{\mathrm{NH}}_{2}\) (III) \(\stackrel{\ominus}{\mathrm{O}} \mathrm{H}\) (IV) \(\stackrel{\ominus}{\mathrm{OR}}\) 
(V) \(\mathrm{RCOO}^{\ominus}\)
  1. I > V > III > IV > II
  2. \(\mathrm{I}>\mathrm{V}>\mathrm{III} \approx \mathrm{~V}>\mathrm{I}\)
  3. V > I > II > IV > III
  4. \(\mathrm{V}>\mathrm{I}>\mathrm{III} \approx \mathrm{IV}>\mathrm{I}\)

Answer

(A) I > V > III > IV > II

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