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Which one of the following compounds is resistant to nucleophilic attack by hydroxyl ions?

1. Methyl acetate
2. Acetonitrile
3. Diethyl ether
4. Acetamide

Correct answer: Diethyl ether

Solution

Diethyl ether is resistant to nucleophilic attack by hydroxyl ions because it lacks an electrophilic carbon atom, unlike the other compounds which have polar bonds susceptible to nucleophilic attack.

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