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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx230

The bromide shown (a 1,4-disubstituted cyclohexane) is converted into the alcohol by SN2 with hydroxide; ignore elimination. Which structure is the product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: D

The drawn bromide is trans-1-bromo-4-methylcyclohexane. SN2 inverts the carbon bearing Br, so OH enters on the face opposite to the departing Br; the methyl-bearing carbon is untouched. The two groups, trans in the bromide, become cis in the alcohol: cis-4-methylcyclohexan-1-ol. The trans-alcohol would need retention, the alkene is elimination, and the ketone needs oxidation (checked by 3D embedding of the SMILES).
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