The compound which does not react with hydroxylamine is

Options

A. `CH_(3)COOH`
B. `CH_(3)COCH_(3)`
C. `CH_(3)CHO`
D. HCHO

Explanation

To determine which compound does not react with hydroxylamine, we first need to understand the nature of hydroxylamine and its reactivity with different types of compounds.

### Step-by-Step Solution:

1. **Understanding Hydroxylamine**:
Hydroxylamine (NH2OH) is a nucleophile that can react with electrophilic centers, particularly carbonyl groups (C=O) found in aldehydes and ketones.

2. **Identifying Carbonyl Compounds**:
Hydroxylamine typically reacts with carbonyl compounds such as aldehydes (RCHO) and ketones (RC(=O)R'). The reaction leads to the formation of oximes, which are characterized by the structure R1R2C=NOH.

3. **Examining Other Functional Groups**:
Hydroxylamine does not react with compounds that lack a carbonyl group or are not electrophilic. For example, carboxylic acids (RCOOH) contain a carbonyl group, but the presence of the hydroxyl group (-OH) adjacent to the carbonyl reduces the electrophilicity of the carbonyl carbon due to resonance. This makes it less susceptible to nucleophilic attack by hydroxylamine.

4. **Conclusion**:
Therefore, the compound that does not react with hydroxylamine is a carboxylic acid. The carbonyl carbon in carboxylic acids is less electrophilic due to the resonance stabilization provided by the adjacent hydroxyl group, preventing the nucleophilic attack by hydroxylamine.

### Final Answer:
The compound that does not react with hydroxylamine is a **carboxylic acid**.

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