The GATE Grind

GATE 2025 CY – Question 25

Organic Chemistry · Oxidation: Oxidation of alcohols involving metal and non-metal-based (chromium, manganese, DMSO, and hypervalent iodine) reagents. Peracid oxidation of alkenes and carbonyls. Alkenes to diols (manganese and osmium-based reagents), alkenes to carbonyls with bond cleavage (ozonolysis), and alkenes to alcohols/carbonyls without bond cleavage (hydroboration-oxidation). Asymmetric epoxidations (Sharpless and Jacobsen) and Sharpless asymmetric hydroxylation. · 1 mark · Multiple select

The correct option(s) of reagents and reaction sequences suitable for carrying out the following transformation is/are

Cyclohexene to cyclohexanone conversion and four reagent sequences.
  1. Option A in the figure
  2. Option B in the figure
  3. Option C in the figure
  4. Option D in the figure

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Show answer and explanation

Correct answer: (A) Option A in the figure; (B) Option B in the figure; (C) Option C in the figure

Explanation

Allylic oxidation followed by conjugate reduction in A or C gives cyclohexanone. Epoxidation and Lewis acid rearrangement in B also gives cyclohexanone. Oxidative diol cleavage in D opens the ring.