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The ketone shown is treated with methylmagnesium bromide, followed by aqueous work-up. What can be said about the product?

  1. AIt is a meso compound
  2. BIt is chiral and formed as a single enantiomer
  3. CIt is chiral and formed as a racemic mixture
  4. DIt is achiral because it has no stereocentre

Answer: D

Cyclohexanone gives 1-methylcyclohexan-1-ol. The carbinol carbon carries OH, CH3 and two identical ring arms (the ring is symmetric about that carbon), so it is not a stereocentre. The product is achiral and has no stereoisomers.
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