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Question

CH3−C|CH3H−O||C−C6H5MCPBA−−−−−→[X]

Major product [X] will be:

A
CH3C|CH3HO||COC6H5
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B
CH3C|CH3HOO||CC6H5
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C
CH3CH2OO||CCH2C6H5
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D
C6H5CH2OO||CCH2CH3
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Solution

The correct option is A CH3C|CH3HOO||CC6H5


This is Baeyer Villiger oxidation.

MCPBA is used to provide one extra oxygen atom, the mechanism is like as shown.
Hence, an alkyl group with higher stability migrates.

Baeyer-Villiger oxidation is regioselective. Of the two alpha carbons in the ketone, the one that can stabilize a positive charge more effectively, which is the more highly substituted one, migrates from carbon to oxygen preferentially.

Migratory aptitude: hydrogen > tertiary alkyl > secondary alkyl > phenyl > primary alkyl > methyl

Hence, option B is correct.

142207_129878_ans_2525341943cb4b0197ca664d8d6b81f2.png

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