A student was studying terpene synthesis, and she wanted to make the compound shown here. First she converted 3-bromo-6-methylcyclohexene to alcohol A. She heated alcohol A with sulfuric acid and purified one of the components (compound B) from the resulting mixture. Compound B has the correct molecular formula for the desired product.
(a) Suggest how 3-bromo-6-methylcyclohexene might be converted to alcohol A.
(b) The UV spectrum of compound B shows λmax at 269 nm. Is compound B the correct product? If not, suggest a structure for compound B consistent with these UV data.
(c) Propose a mechanism for the dehydration of alcohol A to compound B.

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CH3 CH3 H,SO heat Compound B Br CH-C OH CH3 alcohol A desired product