Which of the following reactions does not yield an amine?

Options

A. `R-X+NH_3to`
B. `R-CH=NOH+[H]overset((Na)/(C_2H_5OH))to`
C. `R-CN+H_2Ooverset(H^(+))to`
D. `R-CONH_2overset(LiAlH_4)to`

Explanation

To determine which of the following reactions does not yield an amine, we will analyze each option step by step.

### Step 1: Analyze Option A
- **Reaction**: Alkyl halide reacts with ammonia.
- **Expected Product**: When an alkyl halide (R-X) reacts with ammonia (NH3), it undergoes nucleophilic substitution. The ammonia acts as a nucleophile and replaces the halide ion (X), leading to the formation of an amine (R-NH2) and hydrogen halide (HX).
- **Conclusion**: This reaction yields an amine.

### Step 2: Analyze Option B
- **Reaction**: R-CH=NOH (oxime) is reduced in the presence of sodium and ethyl alcohol.
- **Expected Product**: The reduction of an oxime (R-CH=NOH) typically involves the addition of hydrogen, resulting in the formation of an amine (R-CH2-NH2) and water (H2O).
- **Conclusion**: This reaction also yields an amine.

### Step 3: Analyze Option C
- **Reaction**: Alkyl cyanide undergoes hydrolysis.
- **Expected Product**: Hydrolysis of an alkyl cyanide (R-CN) leads to the formation of a carboxylic acid (R-COOH) and ammonia (NH3). The reaction does not produce an amine.
- **Conclusion**: This reaction does not yield an amine.

### Step 4: Analyze Option D
- **Reaction**: Amide (R-CO-NH2) is reduced using lithium aluminum hydride (LiAlH4).
- **Expected Product**: Lithium aluminum hydride is a strong reducing agent that reduces amides to amines. The product formed is R-CH2-NH2 and water (H2O).
- **Conclusion**: This reaction yields an amine.

### Final Conclusion
After analyzing all the options, we find that the reaction in **Option C** does not yield an amine.

### Summary of Results
- **Option A**: Yields an amine.
- **Option B**: Yields an amine.
- **Option C**: Does not yield an amine (correct answer).
- **Option D**: Yields an amine.