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

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

AIPMTAIPMT 2008Aldehydes Ketones and Carboxylic Acids

Solution:

Acylchloride $>$ Acid anhydride $>$ Ester $>$ Amide
The ease of nucleophilic substitution depends 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 $2$ step. The reactivity of the compound may be explained by the basicity of leaving the group. A weaker base is a better leaving group.
The order of basicity is as;
$Cl ^{-}< RCOO ^{-}< RO ^{-}< NH _{2}^{-}$
Hence order of leaving tendency is $Cl ^{-}> RCOO ^{-}> RO ^{-}> NH _{2}^{-}$and therefore the order of reactivity of acyl compound is as;
Acylchloride $>$ Acid $\backslash$ Anhydride $>$ Ester $>$ Amide