Identify A in the following reaction. [figure]
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Answer
(1) [figure]
Solution
A 2H2/Pt decalin A has the decalin skeleton with two C=C bonds.
Hot KMnO4 cleaves each C=C; every =CH– carbon is oxidised to –COOH.
Products: cyclohexane-1,2-dicarboxylic acid + oxalic acid (HOOC-COOH).
One ring (the cyclohexane ring of the product) is saturated and is not broken.
Both C=C are 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: C1, C4 → two –COOH on adjacent ring carbons; C2-C3 → HOOC-COOH.
This is structure (1).
(2): one double bond is at the ring fusion – its cleavage opens both rings (no cyclohexane-1,2-dicarboxylic acid).
(3), (4): one double bond in each ring – both rings are cleaved and no oxalic acid is formed.
Answer: (1)