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Question

The correct sequence of decreasing order of reactivity of hydrolysis of acid chlorides is :

A
PhCOCl>pO2NC6H4COCl>pCH3OC6H4COCl
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B
PhCOCl>pCH3OC6H4COCl>pO2NC6H4COCl
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C
pO2NC6H4COCl>PhCOCl>pCH3OC6H4COCl
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D
pO2NC6H4COCl>pCH3OC6H4COCl>PhCOCl
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Solution

The correct option is C pO2NC6H4COCl>PhCOCl>pCH3OC6H4COCl
The hydrolysis of acid chloride involves a nucleophilic attack on the fairly positive carbon atom by one of the lone pairs on the oxygen of a water molecule.

PhCOCl+H2OPhCOOH+HCl

More positive carbon will be more reactive for the attack. Presence of NO2 which has M effect makes the C of pNO2C6H4COCl more positive and most reactive. OCH3 with +M effect makes the C less positive and less reactive.

Therefore the order of reactivity is pO2NC6H4COCl>PhCOCl>pCH3OC6H4COCl

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