An alkyl halide on reaction with sodium in the presence of ether gives 2,2,5,5-tetramethylhexane. The alkyl halide is

Options

A. 1-Chloropentane
B. 1-Chloro-2,2-dimethylpropane
C. 3-Chloro-2,2-dimethylbutane
D. 2-Chloro-2methylbutane

Explanation

To determine the alkyl halide that reacts with sodium in the presence of ether to produce 2,2,5,5-tetramethylhexane, we can follow these steps:

### Step 1: Analyze the Product Structure
The product is 2,2,5,5-tetramethylhexane. This indicates that the molecule has a hexane backbone (6 carbon atoms) with two methyl groups attached to the second carbon and two methyl groups attached to the fifth carbon.

### Step 2: Understand the Reaction
The reaction in question is a Wurtz reaction, which involves the coupling of two alkyl halides in the presence of sodium metal and ether. The general reaction can be represented as:
\[ 2 \text{R-X} + 2 \text{Na} \xrightarrow{\text{ether}} \text{R-R} + 2 \text{NaX} \]
where R is the alkyl group and X is the halogen.

### Step 3: Determine the Alkyl Halide
To form 2,2,5,5-tetramethylhexane, we need to identify an appropriate alkyl halide that can provide the necessary carbon skeleton.

1. **Consider the Carbon Count**: Since the product has 6 carbon atoms, we need to start with an alkyl halide that has at least 4 carbon atoms to allow for the coupling to yield a total of 6 carbons.
2. **Identify Possible Alkyl Halides**:
- If we take 1-chloro-3-methylbutane (which has 4 carbons in the chain and 1 chlorine), it can couple with itself to yield the desired product.
- The structure of 1-chloro-3-methylbutane is as follows:
- CH3-CH(CH3)-CH2-CH2-Cl
3. **Perform the Wurtz Reaction**:
- When 1-chloro-3-methylbutane reacts with sodium, it forms the coupling product:
- CH3-CH(CH3)-CH2-CH2 + CH3-CH(CH3)-CH2-CH2 → 2,2,5,5-tetramethylhexane.

### Step 4: Conclusion
The alkyl halide that reacts with sodium in the presence of ether to give 2,2,5,5-tetramethylhexane is **1-chloro-3-methylbutane**.