An alcohol on oxidation is found to give `CH_(3)COOH` and `CH_(3)CH(OH)CH_(2)CH_(2)CH_(3)` The structure of the alcohol is :

Options

A. `CH_(3)CH_(2)CH_(2)OH`
B. `(CH_(3))_(2)C(OH)CH_(2)CH_(3)`
C. `CH_(3)CH_(2)CH(OH)CH_(3)`
D. `CH_(3)CH(OH)CH_(2)CH_(2)CH_(3)`

Answer

To determine the structure of the alcohol that, upon oxidation, yields both acetic acid (CH₃COOH) and 2-pentanol (CH₃CH(OH)CH₂CH₂CH₃), we can follow these steps:

### Step-by-Step Solution:

1. **Identify the Products**:
The products of the oxidation are acetic acid (CH₃COOH) and 2-pentanol (CH₃CH(OH)CH₂CH₂CH₃). This indicates that the starting alcohol must be a secondary alcohol since it can produce two different products upon oxidation.

2. **Determine the Structure of Acetic Acid**:
Acetic acid has the structure CH₃COOH. This suggests that one of the oxidation products is derived from a carbon chain that includes a carbonyl group (C=O) at the end.

3. **Determine the Structure of 2-Pentanol**:
The structure of 2-pentanol is CH₃CH(OH)CH₂CH₂CH₃. This indicates that the alcohol has a hydroxyl (-OH) group on the second carbon of a five-carbon chain.

4. **Combine the Information**:
Since the oxidation of the alcohol yields both acetic acid and 2-pentanol, we can infer that the alcohol must be a secondary alcohol with a five-carbon chain. The presence of both products suggests that the alcohol must be capable of being oxidized to form both a carboxylic acid and an aldehyde.

5. **Propose the Structure of the Alcohol**:
The alcohol that fits this description is 3-pentanol (CH₃CH₂CH(OH)CH₂CH₃). Upon oxidation:
- 3-pentanol can be oxidized to form 2-pentanoic acid (which can further oxidize to acetic acid) and 2-pentanol.

6. **Final Structure**:
Therefore, the structure of the alcohol is:
\[ \text{CH}_3\text{CH}_2\text{CH(OH)}\text{CH}_2\text{CH}_3 \]
This is 3-pentanol.