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

Options

A. Methyl acetate
B. Acetonitrile
C. Acetamide
D. Diethyl ether

Explanation

To determine which compound is resistant to nucleophilic attack by hydroxyl ions, we will analyze each option provided in the question.

### Step-by-Step Solution:

1. **Identify the Compounds**:
We need to evaluate the reactivity of the following compounds towards nucleophilic attack by hydroxyl ions (OH⁻):
- Methyl acetate
- Acetonitrile
- Acetamide
- Diethyl ether

2. **Analyze Methyl Acetate**:
- Structure: CH₃COOCH₃
- Methyl acetate can undergo nucleophilic attack by hydroxyl ions. The hydroxyl ion can attack the carbonyl carbon (C=O), leading to the formation of an alkoxide intermediate, which can further react.
- **Conclusion**: Methyl acetate is not resistant to nucleophilic attack.

3. **Analyze Acetonitrile**:
- Structure: CH₃C≡N
- Acetonitrile has a triple bond between carbon and nitrogen. Hydroxyl ions can attack the carbon atom, resulting in the formation of an intermediate that can lead to further reactions.
- **Conclusion**: Acetonitrile is also not resistant to nucleophilic attack.

4. **Analyze Acetamide**:
- Structure: CH₃CONH₂
- Acetamide contains a carbonyl group (C=O) that can also be attacked by hydroxyl ions. The resulting reaction can lead to the formation of an alcohol and amine.
- **Conclusion**: Acetamide is not resistant to nucleophilic attack.

5. **Analyze Diethyl Ether**:
- Structure: CH₃CH₂OCH₂CH₃
- Diethyl ether has an ether functional group. The oxygen atom in the ether has a lone pair of electrons, which contributes to the stability of the molecule. Hydroxyl ions do not effectively attack the ether due to steric hindrance and the lack of a suitable electrophilic center.
- **Conclusion**: Diethyl ether is resistant to nucleophilic attack by hydroxyl ions.

6. **Final Answer**:
- The compound that is resistant to nucleophilic attack by hydroxyl ions is **Diethyl ether**.