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Which of the following alkanes give exactly one monochloro derivative on free-radical chlorination?

  1. A2,2-Dimethylpropane
  2. B2,2,4,4-Tetramethylpentane
  3. C2,2,3,3-Tetramethylbutane
  4. D2,3-Dimethylbutane

Answer: A, C

Count distinct H types: 2,2-dimethylpropane 1; 2,2,4,4-tetramethylpentane 2 (tert-butyl methyls and the central CH2); 2,2,3,3-tetramethylbutane 1; 2,3-dimethylbutane 2 (CH3 and CH). Exactly one: A, C.
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