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Question

Which of the following compound is resistant to nucleophilic attack of OH− ion?

A
acetamide
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B
acetonitrile
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C
methyl acetate
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D
diethyl ether
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Solution

The correct option is D diethyl ether
Acetamide, acetonitrile and methyl acetate contains an unsaturated carbon atom which can be easily attacked by a nucleophile such as hydroxide ion.

Also C=O group in which oxygen is electronegative so carbon electron defecient on which nucleophile can attack.

In diethyl ether, all carbon atoms are saturated.

Hence, it resists attack by hydroxide ion.

Option D is correct.

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