Which of the following types of carbonyl groups will produce an oxime on reaction with hydroxylamine?

Options

A. `R - underset(O)underset(||)(C ) - OH`
B. `R - underset(O)underset(||)(C ) - H `
C. `R - underset(O)underset(||)(C ) - OCH_(3)`
D. `R - underset(O)underset(||)(C ) - NH - CH_(3)`

Explanation

To determine which types of carbonyl groups will produce an oxime upon reaction with hydroxylamine, we need to analyze the reactivity of different carbonyl compounds.

### Step-by-Step Solution:

1. **Understand the Reactant**: Hydroxylamine (NH2OH) is a reagent that reacts with carbonyl compounds to form oximes. The general structure of an oxime is R1R2C=NOH, where R1 and R2 can be hydrogen or hydrocarbon groups.

**Hint**: Remember that hydroxylamine contains both an amine (NH2) and a hydroxyl (OH) group.

2. **Identify Carbonyl Groups**: The carbonyl groups we are considering include:
- Aldehydes (RCHO)
- Ketones (R2C=O)
- Carboxylic acids (RCOOH)
- Esters (RCOOR')
- Amides (RCONH2)

**Hint**: Carbonyl groups are characterized by the presence of a C=O bond.

3. **Reactivity of Carbonyl Groups**:
- **Aldehydes**: Aldehydes react with hydroxylamine to form oximes. The reaction involves the nucleophilic attack of the nitrogen in hydroxylamine on the carbonyl carbon, followed by dehydration (loss of water).
- **Ketones**: Ketones also react with hydroxylamine to form oximes through a similar mechanism as aldehydes.
- **Carboxylic Acids**: Carboxylic acids do not form oximes when reacted with hydroxylamine because they do not have a suitable carbonyl structure for this reaction.
- **Esters**: Esters do not react with hydroxylamine to form oximes due to the presence of the alkoxy group (R'O) which does not allow for the formation of a stable oxime.
- **Amides**: Amides do not react with hydroxylamine to form oximes because the nitrogen in the amide is already bonded to a carbonyl carbon and does not have the necessary reactivity.

**Hint**: Only the carbonyl groups that can be converted into a double bond with nitrogen (C=N) will form oximes.

4. **Conclusion**: Based on the analysis, the types of carbonyl groups that will produce an oxime upon reaction with hydroxylamine are:
- Aldehydes
- Ketones

Therefore, the answer to the question is that both aldehydes and ketones will produce oximes when reacted with hydroxylamine.

### Final Answer:
Aldehydes and ketones are the types of carbonyl groups that will produce an oxime on reaction with hydroxylamine.

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