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.

For the following reaction, draw the structure of the major product:

Draw the structures of intermediates, if there are any. If applicable, include the stereochemistry of the final product.

Predict the major products of the reaction of 1,2-diethylcyclohex-1-ene with warm, concentrated KMnO₄. Problem-Solving Hint: warm, concentrated KMnO₄ oxidizes the pi bond of an alkene and breaks the double bond entirely, giving carbonyl groups.