Which of the following will not give anisole ?

Options

A. Phenol is reacted with dimethyl sulphate in the presenc of a base
B. Sodium phenoxide is treated with methyl iodide.
C. Diazomethane is reacted with phenol
D. Methyl magnesium iodide is treated with phenol.

Explanation

To determine which of the following options will not give anisole, we will analyze each option step by step.

### Step 1: Analyze Option 1 - Phenol + Dimethyl Sulfate
- **Reaction:** Phenol (C6H5OH) reacts with dimethyl sulfate ((CH3)2SO4) in the presence of a base (e.g., NaOH).
- **Mechanism:** The hydroxyl group (-OH) of phenol is deprotonated by the base, forming phenoxide ion (C6H5O-). This ion then reacts with dimethyl sulfate to form anisole (C6H5OCH3) and methyl sulfate.
- **Conclusion:** This reaction will produce anisole.

### Step 2: Analyze Option 2 - Sodium Phenoxide + Methyl Iodide
- **Reaction:** Sodium phenoxide (C6H5O-Na+) reacts with methyl iodide (CH3I).
- **Mechanism:** The phenoxide ion acts as a nucleophile and attacks the methyl group of methyl iodide, leading to the formation of anisole (C6H5OCH3) and sodium iodide (NaI).
- **Conclusion:** This reaction will also produce anisole.

### Step 3: Analyze Option 3 - Phenol + Diazomethane
- **Reaction:** Phenol (C6H5OH) reacts with diazomethane (CH2N2).
- **Mechanism:** The hydroxyl group of phenol reacts with diazomethane, leading to the formation of anisole (C6H5OCH3) and nitrogen gas (N2) as a byproduct.
- **Conclusion:** This reaction will produce anisole as well.

### Step 4: Analyze Option 4 - Phenol + Methyl Magnesium Iodide
- **Reaction:** Phenol (C6H5OH) reacts with methyl magnesium iodide (CH3MgI).
- **Mechanism:** In this case, the Grignard reagent (methyl magnesium iodide) reacts with the acidic hydroxyl group of phenol, leading to the formation of a phenyl magnesium alkoxide intermediate. This intermediate will not yield anisole but rather a tertiary alcohol after hydrolysis.
- **Conclusion:** This reaction will not produce anisole.

### Final Answer
The option that will not give anisole is **Option 4: Methyl Magnesium Iodide treated with Phenol**.

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