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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx273

Counting enantiomers as separate compounds, how many monochlorination products in total (all stereoisomers) can the alkane shown give?

  1. A4
  2. B5
  3. C6
  4. D8

Answer: C

The alkane (2,2,4-trimethylpentane) has four sets of equivalent hydrogens: the tert-butyl methyls, the CH2, the tertiary CH, and the two equivalent methyls on C-4. Chlorination gives four constitutional isomers; the products from the tert-butyl methyls and from the tertiary CH are achiral, while those from the CH2 and from the C-4 methyls each contain a stereocentre and exist as two enantiomers. Total: 1 + 2 + 1 + 2 = 6 (RDKit count: 6).
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