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Question
Predict the product of the reaction.
Predict the product of the reaction.
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Solution
The correct option is B
The given reaction is a semi-pinacolone rearrangement.
When alkyl halide reacts with AgNO3, the halide (X−) leave the substrate to form a carbocation intermediate.
Since, the given molecule is asymmetric, migration of both akyl group attached to the carbon bearing OH is possible.
But here, the alkyl attached to bridgehead carbon does not migrate because it damage the rigidity of the molecule, so, another alkyl group migrates to form a resonance stablised carbocation. Then, deprotonation occurs to form the final product.
The given reaction is a semi-pinacolone rearrangement.
When alkyl halide reacts with AgNO3, the halide (X−) leave the substrate to form a carbocation intermediate.
Since, the given molecule is asymmetric, migration of both akyl group attached to the carbon bearing OH is possible.
But here, the alkyl attached to bridgehead carbon does not migrate because it damage the rigidity of the molecule, so, another alkyl group migrates to form a resonance stablised carbocation. Then, deprotonation occurs to form the final product.
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