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Question

Which is the most suitable reagent for the following conversion?
CH3CH=CHCH2OCCH3 CH3CH=CHCH2OCOH

A
Tollens' reagent
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B
Benzoyl peroxide
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C
I2 and NaOH solution followed by hydrolysis
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D
LiAlH4/C2H5OH
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Solution

The correct option is C I2 and NaOH solution followed by hydrolysis
a) Ketones are mostly not oxidisable by Tollens' reagent.
b) Benzoyl peroxide can do epoxidation as well as ester formation.
c) I2 and NaOH solution oxidises methyl ketone into sodium carboxylate which on further hydrolysis gives carboxylic acid.
d) LiAlH4/C2H5OH will reduce the ketone into alcohol.

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