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JEE Main · 2020 · 03 Sep 2020 · Shift 1 · General Organic Chemistry

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Which of the following compounds produces an optically inactive compound on hydrogenation?
  1. (A)(see structure)
  2. (B)(see structure)
    ✓ Correct
  3. (C)(see structure)
  4. (D)(see structure)

Answer: (B)

Solution

Hydrogenation gives an optically inactive product when the saturated molecule ends up with a plane of symmetry, either achiral or meso. The structure in which adding hydrogen across the double bond produces such a symmetric compound, superimposable on its mirror image, is the one that becomes optically inactive, while the others remain chiral after hydrogenation.

JEE Main · 2020 · 03 Sep 2020 · Shift 1 · Single correct option

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