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Compound A (C7H11Br) is treated with magnesium in ether to

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 47SP Chapter 10

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 47SP

Compound A (C7H11Br) is treated with magnesium in ether to give B( C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D ( C10H18O). Heating D with concentrated H2SO4 gives E( C10H16), which decolorizes two equivalents of Br2 to give F( C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.

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Solution 47SP

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Chapter 10, Problem 47SP is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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