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JEE Advanced levelSingle correct optionDifficulty 3 of 3st327

The compound shown is 2-chloropentane (no configuration specified). The total number of isomers of molecular formula , counting constitutional isomers and enantiomers separately, is

  1. A8
  2. B10
  3. C11
  4. D12

Answer: C

Pentane skeleton: 1-, 2- and 3-chloropentane (3). 2-Methylbutane skeleton: 1-chloro-2-methylbutane, 2-chloro-2-methylbutane, 2-chloro-3-methylbutane and 1-chloro-3-methylbutane (4). 2,2-Dimethylpropane skeleton: 1-chloro-2,2-dimethylpropane (1). That is 8 constitutional isomers. Three of them have a stereocentre: 2-chloropentane, 1-chloro-2-methylbutane and 2-chloro-3-methylbutane, each giving a pair of enantiomers. 3-Chloropentane is achiral (two ethyl groups). Total = 8 + 3 = 11.
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