Which one of the following esters gets hydrolysed most easily under alkaline conditions?
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Answer
(4) [figure]
Solution
Alkaline hydrolysis of an ester is a nucleophilic acyl substitution: OH- attacks the carbonyl carbon and the phenoxide ion is expelled.
⇒ The reaction is fastest when the carbonyl carbon is most electrophilic and the leaving phenoxide ion is most stable (i.e. the corresponding phenol is most acidic).
-NO2 at the para position is strongly electron-withdrawing (–I, –R); it stabilises the phenoxide ion by resonance and makes the acyl carbon more electrophilic.
∴ Order of ease of hydrolysis (para substituent): NO2 > Cl > H > OCH3
Answer: (4)