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Question

Among the given compounds, the compound which is most susceptible to a nucleophilic attack at the carbonyl group is :

A
CH3COCl
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B
CH3CHO
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C
CH3COOCH3
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D
CH3COOCOCH3
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Solution

The correct option is B CH3COCl
We know the following facts:
1. Weaker bases are better leaving groups.
2. Strong acids have very weak conjugate bases.
Here, HCl is a very strong acid.
So, the chloride ion is a very weak base as compared to others.
Hence, it is the best leaving group in nucleophilic acyl substitution.
Besides, the Cl group also activates the carbonyl group towards nucleophilic substitution reaction due to its I effect.
Therefore, CH3COCl is most susceptible to nucleophilic attack at the carbonyl group because it will show fastest rate of reaction.

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