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Oxidative Cleavage
10. Addition Reactions / Oxidative Cleavage / Problem 1

An unknown compound is placed in Br2/CCl­4 solution, and the brownish-red color of the solution disappears. It also undergoes catalytic hydrogenation to form dodecahydroheptalene. The compound forms cis- cycloheptane-1,2-dicarboxylic acid and malonic acid when treated with warm, concentrated potassium permanganate. Determine the structure of the unknown compound.

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