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problem_set_x_answers

problem_set_x_answers - CHEM 302 Organic Chemistry I...

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CHEM 302 Organic Chemistry I Problem Set X Chapter 10 Answers 1) Draw the expected hydrocarbons when the alkenes below are treated with H 2 /PtO 2 and identify the major product in each case. Briefly explain your reasoning. a) b) H H c) a) H CH 3 H H The top face is blocked, so the bottom face is the only one which is accessible for the reduction. The other isomer can form but in very minor amounts. b) H H H H major minor The top face is blocked by the cyclopropyl group, so the bottom face is the more accessible.
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c) major minor Here we have the same reasons as above; the top face is hindered by the isopropyl group. Are you getting the idea that hindrance is important? 2) Give the expected major product from each of the following reactions. Pay attention to stereochemistry where appropriate. a) Br 2 CH 3 Br Br (remember, it said major ) b) Br 2 CH 3 OH Br OCH 3
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3) Compound A (C 10 H 16 ) yields 1-isopropyl-4-methylcyclohexane on hydrogenation over PtO 2 . Treatment of A with ozone followed by oxidative work-up using hydrogen peroxide gives the compound shown below and formic acid (HCOOH).
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