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An alkyl chloride A with molecular formula C4H9Cl is treated with sodium in dry ether. The hydrocarbon formed on this reaction yields only one monochloro product when chlorinated. Identify A.

1. tert-Butyl chloride
2. sec-Butyl chloride
3. isobutyl chloride
4. n-Butyl chloride

Correct answer: tert-Butyl chloride

Solution

Wurtz coupling doubles the carbon skeleton. tert-Butyl chloride gives (CH3)3C-C(CH3)3 (2,2,3,3-tetramethylbutane), in which all 18 hydrogens are equivalent, so chlorination yields only one monochloro product.

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