Which set of the following compound(s) give benzene on reaction with PhMgBr?

Options

A.
B.
C.
D. `CH_(3)NH_(2),CH_(3)-CH_(2)-SH`

Explanation

To determine which set of compounds gives benzene upon reaction with PhMgBr (phenylmagnesium bromide), we need to identify compounds that contain acidic hydrogens. These acidic hydrogens can react with the Grignard reagent, leading to the formation of benzene.

### Step-by-Step Solution:

1. **Understanding Grignard Reagents**:
- Grignard reagents like PhMgBr are highly reactive and can deprotonate compounds that have acidic hydrogens.
- Acidic hydrogens are typically found in functional groups such as -OH (alcohols), -NH (amines), -SH (thiols), and -C≡CH (alkynes).

2. **Identifying Acidic Hydrogens**:
- We need to analyze the given compounds to see if they contain any of the aforementioned functional groups with acidic hydrogens.
- For example:
- Alcohols (R-OH) have acidic hydrogens.
- Amines (R-NH2) can also have acidic hydrogens.
- Thiols (R-SH) have acidic hydrogens.
- Terminal alkynes (R-C≡CH) have acidic hydrogens.

3. **Reactions with PhMgBr**:
- When a compound with an acidic hydrogen reacts with PhMgBr, the acidic hydrogen is replaced by a phenyl group, resulting in the formation of benzene.
- For instance:
- If we take an alcohol (R-OH), the reaction would be:
\[ R-OH + PhMgBr \rightarrow R-Ph + Mg(OH)Br \]
where R-Ph is a phenyl-substituted compound, and the byproduct is magnesium hydroxide bromide.

4. **Conclusion**:
- If all the compounds listed in the question contain acidic hydrogens, they will all react with PhMgBr to produce benzene.
- Therefore, the answer to the question is that all the given compounds will yield benzene upon reaction with PhMgBr.

### Final Answer:
All of the compounds listed will give benzene upon reaction with PhMgBr.

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