Which of the following can be used to prepare methyl phenyl ether?

Options

A. Reaction sodium phenolate and methyl chloride
B. Phenol with `CH_(2)N_(2)`
C. `CH_(3)O^(-)Na^(+)` with chlorobenzene
D. Reacting `PhO^(-)Mg^(+)Cl` with PhCl

Answer

To prepare methyl phenyl ether, we need to identify which of the given options can successfully yield this compound through a chemical reaction. Let's analyze each option step by step.

### Step-by-Step Solution:

1. **Option 1: Sodium Phenolate and Methyl Chloride**
- Sodium phenolate (C6H5O^-Na^+) can react with methyl chloride (CH3Cl).
- The oxygen atom in sodium phenolate acts as a nucleophile and attacks the carbon atom of the methyl chloride, which is a good electrophile.
- This reaction follows an SN2 mechanism, leading to the formation of methyl phenyl ether (C6H5OCH3) and sodium chloride (NaCl) as a byproduct.
- **Conclusion**: This option can be used to prepare methyl phenyl ether.

2. **Option 2: Phenol and Methyl Hydrazine (CH3NH2)**
- Phenol (C6H5OH) can react with methyl hydrazine (CH3NH2).
- In this reaction, the nitrogen atom in methyl hydrazine abstracts a proton from phenol, forming phenoxide ion (C6H5O^-).
- The phenoxide ion then attacks the methyl group of methyl hydrazine, leading to the formation of methyl phenyl ether (C6H5OCH3) and nitrogen gas (N2) as a byproduct.
- **Conclusion**: This option can also be used to prepare methyl phenyl ether.

3. **Option 3: Chlorobenzene and Sodium Methoxide**
- Chlorobenzene (C6H5Cl) can react with sodium methoxide (CH3O^-Na^+).
- In the presence of a cupric salt, sodium methoxide acts as a nucleophile and attacks the carbon atom of chlorobenzene, displacing the chloride ion (Cl^-).
- This reaction also follows an SN2 mechanism and produces methyl phenyl ether (C6H5OCH3) along with sodium chloride (NaCl).
- **Conclusion**: This option can be used to prepare methyl phenyl ether.

4. **Option 4: Phenyl Magnesium Bromide (C6H5MgBr)**
- In this case, phenyl magnesium bromide is a Grignard reagent and is not suitable for forming methyl phenyl ether directly.
- If the oxygen of the ether were to attack the carbon of the Grignard reagent, it would not yield methyl phenyl ether but rather lead to an undesired reaction.
- Therefore, this option does not yield methyl phenyl ether.
- **Conclusion**: This option cannot be used to prepare methyl phenyl ether.

### Final Answer:
The options that can be used to prepare methyl phenyl ether are **1, 2, and 3**.