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An organic compound A (C4H9Cl) on reaction with Na/diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative, then A is:

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

Correct answer: tert-butyl chloride

Solution

The compound A is tert-butyl chloride because the reaction with Na/diethyl ether (Wurtz reaction) forms 2,2,3,3-tetramethylbutane, which on monochlorination gives only one product due to its symmetrical structure.

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