An organic compound of molecular formula `C_(3)H_(6)O` did not give a silver mirror with with Tollens' reagent but give an oxime with hydroxylamine. It may be

Options

A. `CH_(2)=CH-CH_(2)-OH`
B. `CH_(3)COCH_(3)`
C. `CH_(3)CH_(2)CHO`
D. `CH_(2)=CH-OCH_(3)`

Answer

To solve the problem, we need to analyze the given information about the organic compound with the molecular formula \( C_3H_6O \).

### Step 1: Identify the functional groups
The molecular formula \( C_3H_6O \) suggests that the compound could be an aldehyde, ketone, or alcohol. However, the key information provided is that the compound does not give a silver mirror with Tollens' reagent. This indicates that the compound is not an aldehyde, as aldehydes typically react with Tollens' reagent to produce a silver mirror.

**Hint:** Recall that Tollens' reagent is used to test for aldehydes, which reduce silver ions to metallic silver.

### Step 2: Determine the possible types of compounds
Since the compound is not an aldehyde, we can consider the possibility of it being a ketone or an alcohol. However, the problem states that the compound gives an oxime with hydroxylamine, which is a reaction characteristic of carbonyl compounds (aldehydes and ketones).

**Hint:** Oximes are formed from carbonyl compounds (aldehydes and ketones) when they react with hydroxylamine.

### Step 3: Analyze the reaction with hydroxylamine
The formation of an oxime indicates that the compound must contain a carbonyl group (C=O). Since we have already established that it is not an aldehyde, it must be a ketone. For example, if the compound were propanone (acetone), it would react with hydroxylamine to form propanone oxime.

**Hint:** Ketones react with hydroxylamine to form oximes, while aldehydes do the same but are ruled out here.

### Step 4: Confirm the structure of the ketone
The molecular formula \( C_3H_6O \) corresponds to propanone (acetone), which is a ketone. The structure of propanone is:

\[ \text{CH}_3\text{C(=O)}\text{CH}_3 \]

This confirms that the compound is indeed a ketone, as it has the required carbonyl group.

**Hint:** Check the structural formula to ensure it matches the molecular formula given.

### Step 5: Conclusion
Based on the analysis, the organic compound with the molecular formula \( C_3H_6O \) that does not give a silver mirror with Tollens' reagent but gives an oxime with hydroxylamine is propanone (acetone).

**Final Answer:** The compound is a ketone, specifically propanone (acetone).