The reduction of which compound does not yield `C_2 H_5 NH_2` ?

Options

A. `C_2 H_5NO_2`
B. `CH_3-CH=NOH`
C. `CH_3NC`
D. `CH_3CN`

Answer

To determine which compound does not yield ethyl amine (C2H5NH2) upon reduction, we need to analyze the reduction process for each of the given compounds.

### Step-by-Step Solution:

1. **Understanding Reduction**:
- Reduction involves the addition of hydrogen or the removal of oxygen, resulting in an increase in the number of C-H bonds. In organic chemistry, this often means converting functional groups like nitro groups or nitriles into amines.

2. **Analyzing the Compounds**:
- **Option A: Nitroethane (C2H5NO2)**:
- Nitroethane can be reduced using reagents like Sn/HCl or Fe/HCl to yield ethyl amine (C2H5NH2).

- **Option B: Oxim (C2H5NO)**:
- Oxims can also be reduced using LiAlH4 or NaBH4 to yield the corresponding primary amine, which in this case is ethyl amine (C2H5NH2).

- **Option C: Isocyanide (CH3NC)**:
- Isocyanides can be reduced, but they do not yield ethyl amine. Instead, they typically yield a different type of amine due to the structure of the isocyanide.

- **Option D: Ethyl Nitrile (C2H5CN)**:
- Ethyl nitrile can be reduced to yield ethyl amine (C2H5NH2) using hydrogenation methods.

3. **Conclusion**:
- After analyzing all options, we find that the compound that does not yield ethyl amine upon reduction is **Option C: Isocyanide (CH3NC)**.

### Final Answer:
The compound that does not yield ethyl amine (C2H5NH2) upon reduction is **C: Isocyanide (CH3NC)**.

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