The correct sequence of decreasing order of reactivity of hydrolysis of acid chlorides is :
A
PhCOCl>p−O2NC6H4COCl>p−CH3OC6H4COCl
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B
PhCOCl>p−CH3OC6H4COCl>p−O2NC6H4COCl
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C
p−O2NC6H4COCl>PhCOCl>p−CH3OC6H4COCl
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D
p−O2NC6H4COCl>p−CH3OC6H4COCl>PhCOCl
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Solution
The correct option is Cp−O2NC6H4COCl>PhCOCl>p−CH3OC6H4COCl 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+H2O→PhCOOH+HCl
More positive carbon will be more reactive for the attack. Presence of −NO2 which has −M effect makes the C of p−NO2C6H4COCl more positive and most reactive. OCH3 with +M effect makes the C less positive and less reactive.
Therefore the order of reactivity is p−O2NC6H4COCl>PhCOCl>p−CH3OC6H4COCl