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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g3083

Which of the following optically active ketones lose their optical activity when stirred with dilute aqueous for some time?

  1. A(R)-3-Methylcyclohexan-1-one
  2. B(R)-2-Methylcyclohexan-1-one
  3. C(S)-3-Methylpentan-2-one
  4. D(S)-4-Methylhexan-2-one

Answer: B, C

Racemisation by base needs the stereocentre to be an alpha carbon bearing H, because enolisation destroys it (the enolate is planar there). In 2-methylcyclohexanone, C-2 is alpha. In 3-methylpentan-2-one, C-3 is alpha. In 3-methylcyclohexanone and 4-methylhexan-2-one the stereocentre is beta and is untouched, so these keep their activity.
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