Which of the following compounds 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 (OH⁻), we will analyze each of the given compounds: methyl acetate, acetonitrile, acetamide, and diethyl ether.

### Step 1: Identify the Compounds
1. **Methyl Acetate (CH₃COOCH₃)**: This is an ester.
2. **Acetonitrile (CH₃CN)**: This is a nitrile.
3. **Acetamide (CH₃CONH₂)**: This is an amide.
4. **Diethyl Ether (C₂H₅)₂O**: This is an ether.

### Step 2: Analyze Nucleophilic Attack
- **Methyl Acetate**: The carbonyl carbon in the ester is electrophilic and can be attacked by hydroxyl ions. Therefore, it is not resistant to nucleophilic attack.

- **Acetonitrile**: The carbon in the nitrile group (C≡N) can also be attacked by nucleophiles. Thus, acetonitrile is not resistant to nucleophilic attack.

- **Acetamide**: The carbonyl carbon in the amide can be attacked by hydroxyl ions as well, making it susceptible to nucleophilic attack.

- **Diethyl Ether**: Ethers have an oxygen atom bonded to two alkyl groups. They do not have a carbonyl group or any acidic hydrogen that can be easily removed. Therefore, they are generally resistant to nucleophilic attack by hydroxyl ions.

### Step 3: Conclusion
Among the four compounds, **diethyl ether** is the only compound that is resistant to nucleophilic attack by hydroxyl ions.

### Final Answer:
The compound that is resistant to nucleophilic attack by hydroxyl ions is **diethyl ether**.

---