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Question 63

Identify A in the following reaction.

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Step 1: Catalytic Hydrogenation (H₂ / Pt)

  • Product formed is a fully saturated fused bicyclic compound (decalin)
  • This means all double bonds in A are reduced
  • Since 2H₂ are used, A must contain two double bonds
  • The fused ring structure indicates both double bonds are within the ring system
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Step 2: Oxidation with hot KMnO₄ (Δ)

  • Hot KMnO₄ cleaves double bonds
  • Products given:
    • One cyclohexane ring with two -COOH groups
    • One oxalic acid (HOOC-COOH)
  • Formation of oxalic acid indicates a double bond between two carbons each having H
  • This confirms both double bonds are present in the same ring, arranged such that cleavage gives oxalic acid

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