Which of the following compound give a secondary amine on reduction ?

Options

A. nitromethane
B. oxime
C. methyl cyanide
D. methyl isocyanide

Explanation

To determine which compound gives a secondary amine upon reduction, we need to analyze the compounds provided and understand the reduction processes that lead to secondary amines.

### Step-by-Step Solution:

1. **Understanding Secondary Amines**:
- A secondary amine is formed when a compound undergoes reduction, resulting in an amine with two organic groups attached to the nitrogen atom.

2. **Identifying Suitable Compounds**:
- Common compounds that can yield secondary amines upon reduction include keto-oximes and isocyanides.
- For example, a keto-oxime formed from a ketone and hydroxylamine can be reduced to a secondary amine.

3. **Keto-Oxime Reduction**:
- Consider a ketone (like acetone) reacting with hydroxylamine (NH2OH) to form a keto-oxime.
- The reaction can be represented as:
\[ \text{Ketone} + \text{Hydroxylamine} \rightarrow \text{Keto-Oxime} + \text{H}_2\text{O} \]
- When this keto-oxime is reduced using sodium in ethanol, it yields a secondary amine.

4. **Isocyanide Reduction**:
- Another pathway is the reduction of isocyanides.
- For instance, methyl isocyanide can be reduced with hydrogen to yield a secondary amine:
\[ \text{Methyl Isocyanide} + \text{H}_2 \rightarrow \text{Secondary Amine} \]

5. **Evaluating Options**:
- Now, we need to evaluate the given options:
- **Nitromethane**: Reducing nitromethane does not yield a secondary amine; it gives a primary amine.
- **Methyl Cyanide**: Reducing methyl cyanide will yield a primary amine, not a secondary amine.
- **Methyl Isocyanide**: This compound can be reduced to yield a secondary amine.

6. **Conclusion**:
- Based on the analysis, the compound that gives a secondary amine upon reduction is **methyl isocyanide**.

### Final Answer:
The compound that gives a secondary amine on reduction is **methyl isocyanide**.

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