Identify A in the following reaction. [figure]
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Answer
(1) [figure]
Solution
A 2H2/Pt decalin, so A has the decalin skeleton with two C=C bonds.
Hot KMnO4 cleaves each C=C, and every =CH– carbon is oxidised to –COOH; the products are cyclohexane-1,2-dicarboxylic acid and oxalic acid (HOOC-COOH).
Since the cyclohexane ring of the product is not broken, one ring is saturated, so both C=C must be in the other ring as a diene C1=C2-C3=C4, with C1 and C4 bonded to the two ring-fusion carbons.
Cleavage of C1=C2 and C3=C4 turns C1 and C4 into two –COOH on adjacent ring carbons, while C2-C3 becomes HOOC-COOH. This is structure (1).
(2): one double bond is at the ring fusion, so its cleavage opens both rings (no cyclohexane-1,2-dicarboxylic acid).
(3), (4): there is one double bond in each ring, so both rings are cleaved and no oxalic acid is formed.
Answer: (1)