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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2261

The alkane shown is monochlorinated with and light, and the whole chloride mixture is then heated with alcoholic (E2, every available beta hydrogen counted). How many different alkenes (constitutional isomers) can be obtained in total?

  1. A2
  2. B3
  3. C4
  4. D5

Answer: B

The alkane is 2-methylbutane, which gives four chlorides. Dehydrochlorination gives 2-methylbut-1-ene (from 1-chloro-2-methyl and 2-chloro-2-methyl), 2-methylbut-2-ene (from the tertiary and the 2-chloro-3-methyl chloride) and 3-methylbut-1-ene (from 1-chloro-3-methyl and 2-chloro-3-methyl). Only three distinct alkenes result.
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