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Question

The order of reactivity of phenyl magnesium bromide (PhMgBr) with the following compounds


and I II III

A
III>II>I
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B
I>III>II
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C
I>II>III
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D
II>I>III
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Solution

The correct option is C I>II>III
The reactivity of the carbonyl group towards the nucleophilic addition reactions depends upon the magnitude of the positive charge on the carbonyl carbon atom (electronic factor) and also on the crowding around the carboxyl carbon atom in the transition state (steric factor). Both these factors predict the following order.
CH3 is electron donating group, it will reduce the partial positive charge on carbonyl carbon.

Thus, the order of reactivity of PhMgBr follows the order,

Hence, option (d) is correct.

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