Which of the following reactions will give ether as main product?

Options

A.
B. `Me_(3)C-OH underset(C_(6)H_(5)Br)overset(Na)to`
C. `Me_(3)C-OH underset(CH_(3)CH_(2)CH_(2)Br)overset(Na)to`
D. ` CH_(3)CH_(2)CH_(2)OH underset(Me_(3)C-Br)overset(Na)to`

Answer

To determine which of the given reactions will produce ether as the main product, we need to analyze each option step by step.

### Step 1: Analyze Reaction A
- **Reaction**: Phenol (C6H5OH) treated with Na in the presence of C2H5Br.
- **Mechanism**:
1. Sodium (Na) will react with phenol, deprotonating it to form sodium phenoxide (C6H5O^-Na^+).
2. The sodium phenoxide then reacts with C2H5Br. The bromine (Br^-) will leave, and the ethyl group (C2H5^+) will attach to the oxygen.
- **Product**: Ethyl phenyl ether (C6H5O-C2H5).
- **Conclusion**: This reaction produces ether.

### Step 2: Analyze Reaction B
- **Reaction**: tert-Butyl alcohol (Me3COH) treated with Na in the presence of C6H5Br.
- **Mechanism**:
1. Sodium will deprotonate tert-butyl alcohol to form tert-butoxide (Me3CO^-Na^+).
2. The presence of C6H5Br will not lead to a reaction because the tert-butoxide is stabilized by resonance with the aromatic ring.
- **Product**: No ether is formed.
- **Conclusion**: This reaction does not produce ether.

### Step 3: Analyze Reaction C
- **Reaction**: tert-Butyl alcohol (Me3COH) treated with Na in the presence of C3H7Br.
- **Mechanism**:
1. Sodium deprotonates tert-butyl alcohol to form tert-butoxide (Me3CO^-Na^+).
2. The bromine (Br^-) from C3H7Br will leave, and the alkyl group (C3H7^+) will attach to the oxygen.
- **Product**: tert-Butyl ether (Me3CO-C3H7).
- **Conclusion**: This reaction produces ether.

### Step 4: Analyze Reaction D
- **Reaction**: Propanol (CH3CH2CH2OH) treated with Na in the presence of Me3CBr.
- **Mechanism**:
1. Sodium deprotonates propanol to form propoxide (CH3CH2CH2O^-Na^+).
2. The presence of Me3CBr will lead to the formation of a carbocation, which is unstable and will not lead to ether formation.
- **Product**: Instead of ether, an alkene is formed due to the instability of the carbocation.
- **Conclusion**: This reaction does not produce ether.

### Final Conclusion
The reactions that produce ether as the main product are:
- **Reaction A**: Phenol with C2H5Br.
- **Reaction C**: tert-Butyl alcohol with C3H7Br.

### Summary of Ether-Producing Reactions:
- **A**: Produces ether (Ethyl phenyl ether).
- **C**: Produces ether (tert-Butyl ether).
- **B**: Does not produce ether.
- **D**: Does not produce ether.