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Chemistry, 20.05.2021 20:10 cookies1164

Compound A (C 7H 11Br) is treated with magnesium in ether to give B (C 7H 11MgBr), which reacts violently with D 2O to give 1-methylcyclohexene with a deuterium atom on the methyl group C. Reaction of B with acetone (CH 3COCH 3) followed by hydrolysis gives D (C 10H 18O). Heating D with concentrated H 2SO 4 gives E (C 10H 16), which decolorizes two equivalents of Br 2 to give F (C 10H 16Br 2). E undergoes hydrogenation with excess H 2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.

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