Which of the following does not give ethylamine on reduction

Options

A. methyl cyanide
B. Ethyl nitrile
C. Nitro ethane
D. Acetamide

Answer

To determine which compound does not yield ethylamine upon reduction, we need to analyze the reduction products of the given compounds. Ethylamine has the structure CH3-CH2-NH2.

Let's go through the options step by step:

1. **Identify the Compounds**: We need to consider the following compounds:
- Methyl cyanide (CH3-C≡N)
- Ethyl cyanide (CH3-CH2-C≡N)
- Nitroethane (CH3-CH2-NO2)
- Acetamide (CH3-CO-NH2)

2. **Reduction of Methyl Cyanide**:
- Methyl cyanide (CH3-C≡N) when reduced with lithium aluminum hydride (LiAlH4) gives:
\[ \text{CH}_3\text{-C}\equiv\text{N} \xrightarrow{LiAlH_4} \text{CH}_3\text{-CH}_2\text{-NH}_2 \]
- This results in ethylamine.

3. **Reduction of Ethyl Cyanide**:
- Ethyl cyanide (CH3-CH2-C≡N) when reduced gives:
\[ \text{CH}_3\text{-CH}_2\text{-C}\equiv\text{N} \xrightarrow{LiAlH_4} \text{CH}_3\text{-CH}_2\text{-CH}_2\text{-NH}_2 \]
- This results in propylamine, not ethylamine.

4. **Reduction of Nitroethane**:
- Nitroethane (CH3-CH2-NO2) when reduced with tin and hydrochloric acid (Sn/HCl) gives:
\[ \text{CH}_3\text{-CH}_2\text{-NO}_2 \xrightarrow{Sn/HCl} \text{CH}_3\text{-CH}_2\text{-NH}_2 \]
- This results in ethylamine.

5. **Reduction of Acetamide**:
- Acetamide (CH3-CO-NH2) when reduced with lithium aluminum hydride gives:
\[ \text{CH}_3\text{-CO-NH}_2 \xrightarrow{LiAlH_4} \text{CH}_3\text{-CH}_2\text{-NH}_2 \]
- This also results in ethylamine.

6. **Conclusion**:
- Among the compounds analyzed, ethyl cyanide is the only one that does not yield ethylamine upon reduction. Instead, it produces propylamine.

Thus, the answer is **ethyl cyanide**.