Q.

How many hydrogens in the compound below are replaced by deuterium when it is shaken in D2O containing trace of hydroxide ion?

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answer is 3.

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Detailed Solution

There are 3-α-H-atoms which are acidic due to EWG ( >C = 0) and they can be replaced by deuterium in basic medium as shown by circle.

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How many hydrogens in the compound below are replaced by deuterium when it is shaken in D2O containing trace of hydroxide ion?