The substance that gives a primary amine on hydrolysis is

Options

A. nitroparaffin
B. alkyl cyanide
C. oxime
D. alkyl isocyanide.

Answer

To determine the substance that gives a primary amine upon hydrolysis, we will analyze each option provided in the question.

### Step-by-Step Solution:

1. **Analyze the First Option: Nitroparaffin (CH3NH2NO2)**
- Nitroparaffin undergoes hydrolysis in the presence of sulfuric acid.
- The products formed are acetic acid (CH3COOH) and hydroxylamine (NH2OH).
- Hydroxylamine is not a primary amine; therefore, this option is incorrect.

2. **Analyze the Second Option: Alkyl Cyanide (R-C≡N)**
- Alkyl cyanide undergoes hydrolysis to yield a carboxylic acid (R-COOH) and ammonia (NH3).
- Ammonia is not a primary amine; thus, this option is also incorrect.

3. **Analyze the Third Option: Oxime (R-C=N-OH)**
- Oxime, which is derived from ketones or aldehydes, undergoes hydrolysis.
- The products formed are a carbonyl compound (R-CO-R) and hydroxylamine (NH2OH).
- Again, hydroxylamine is not a primary amine, making this option incorrect as well.

4. **Analyze the Fourth Option: Alkyl Isocyanide (R-N=C=O)**
- Alkyl isocyanide undergoes hydrolysis.
- The products formed are a primary amine (RNH2) and a carbonyl compound (H-C=O).
- Since we obtain a primary amine from this reaction, this option is correct.

### Conclusion:
The substance that gives a primary amine on hydrolysis is **alkyl isocyanide (Option D)**.