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(7) In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the e label Compound A: CH Government

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(7) In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the e label "Compound A: CH" Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound Areacts with 1 mole equivalent of hydrogen; and, after treatment with acidic KMnO.. Compound Agives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mole equivalent of hydrogen, but yields cyclohexanone after treatment with acidic KMnO.. HO-C-CHCH,CH,CH-C-OH CH3 Compound C cydohet anone How many degrees of unsaturation does Compound A possess? What are the structures of A and B? What was the other product formed in the KMnO, oxidation of B? (5) Outline a straightforward synthetic route to prepare the following compound from acetylene and any other readily available reagents. 3. (4) When 3,6-dimethylcyclohexene is reacted with dry gaseous HBr, one of the products is 1-bromo-1,4- dimethylcyclohexane. Provide a detailed step-by-step mechanism showing electron flow to explain the formation of this product.

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