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JEE Main levelSingle correct optionDifficulty 2 of 3o2255

The alkane shown is monochlorinated with under light. Which statement about the secondary-chloride fraction is correct?

  1. AIt is a racemic mixture of (R)- and (S)-2-chlorobutane.
  2. BIt is pure (R)-2-chlorobutane.
  3. CIt is pure (S)-2-chlorobutane.
  4. DIt is the meso form of 2-chlorobutane.

Answer: A

The alkane is butane. Abstraction of a secondary H gives the planar, achiral sec-butyl radical, and transfers chlorine to either face with equal probability. 2-Chlorobutane therefore forms as a racemic mixture; a meso form is impossible because the molecule has only one stereocentre.
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