Which of the following will not give a primary amine ?

Options

A. `CH_(3)CN overset(LiAIH_(4)) to`
B. `CH_(3)N'C overset(LiAIH_(4)) to`
C. `CH_(3)CONH_(2)to`
D. `CH_(3)CONH_(2) overset(Br_(4).NaOH) to`

Explanation

To determine which of the given compounds will not yield a primary amine upon reduction, we will analyze each option step by step.

### Step 1: Analyze the first compound (CH3-C≡N)
- The first compound is CH3-C≡N (methyl cyanide or acetonitrile).
- When this compound is reduced using a strong reducing agent like LiAlH4, it undergoes reduction to form CH3-CH2-NH2 (ethylamine).
- **Conclusion**: This compound gives a primary amine.

### Step 2: Analyze the second compound (CH3-NC)
- The second compound is CH3-NC (isocyanide).
- Upon reduction with LiAlH4, isocyanides yield secondary amines. The product formed is CH3-CH(NH2)-CH3 (a secondary amine).
- **Conclusion**: This compound does not give a primary amine.

### Step 3: Analyze the third compound (CH3-C(=O)-NH2)
- The third compound is CH3-C(=O)-NH2 (acetamide).
- When acetamide is reduced with LiAlH4, it converts to CH3-CH2-NH2 (ethylamine).
- **Conclusion**: This compound gives a primary amine.

### Step 4: Analyze the fourth compound (CH3COONH2)
- The fourth compound is CH3COONH2 (urea).
- When urea is treated with Br2 in the presence of NaOH (Hofmann degradation), it yields CH3NH2 (methylamine), which is a primary amine.
- **Conclusion**: This compound gives a primary amine.

### Final Conclusion:
From the analysis, the compound that does not yield a primary amine is the second compound (CH3-NC), which gives a secondary amine instead.

### Answer:
**Option 2 (CH3-NC) will not give a primary amine.**

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