The compound which does not lead to benzoic acid by oxidation with `KMnO_(4)` is

Options

A. toluene
B. benzyl alcohol
C. n-butylbenzene
D. t-butylbenzene

Explanation

To determine which compound does not lead to benzoic acid upon oxidation with KMnO4, we will analyze each option provided.

### Step-by-Step Solution:

1. **Understanding the Compounds**:
- We have four options: Toluene, Benzyl Alcohol, N-butylbenzene, and Tertiary Butyl Benzene.
- Each of these compounds has different structures and functional groups.

2. **Oxidation with KMnO4**:
- KMnO4 is a strong oxidizing agent. It can oxidize compounds that contain hydrogen atoms attached to carbon atoms that can be oxidized to carboxylic acids (like benzoic acid).

3. **Analyzing Each Option**:
- **Option A: Toluene (C7H8)**:
- Toluene has a methyl group (CH3) attached to the benzene ring. The methyl group can be oxidized to a carboxylic acid (benzoic acid) when treated with KMnO4.
- **Conclusion**: Toluene can be oxidized to benzoic acid.

- **Option B: Benzyl Alcohol (C7H8O)**:
- Benzyl alcohol has a hydroxyl group (OH) attached to a benzene ring. This alcohol can be easily oxidized to benzoic acid.
- **Conclusion**: Benzyl alcohol can also be oxidized to benzoic acid.

- **Option C: N-butylbenzene (C10H14)**:
- N-butylbenzene has a butyl group (C4H9) attached to the benzene ring. The butyl group contains hydrogen atoms that can be oxidized to form benzoic acid.
- **Conclusion**: N-butylbenzene can be oxidized to benzoic acid.

- **Option D: Tertiary Butyl Benzene (C10H14)**:
- Tertiary butyl benzene has a tertiary butyl group (C(CH3)3) attached to the benzene ring. This group does not have any hydrogen atoms that can be oxidized to form carboxylic acids.
- **Conclusion**: Tertiary butyl benzene cannot be oxidized to benzoic acid.

4. **Final Answer**:
- The compound that does not lead to benzoic acid by oxidation with KMnO4 is **Option D: Tertiary Butyl Benzene**.