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CHEM 316 - problem%20set%209%20solutions

CHEM 316 - problem%20set%209%20solutions - Chem 316 Problem...

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Br D D OH Br Br H H O O O O Problem Set 9 Solutions Chem 316 1. Complete the following reactions. Be sure to show any relevant stereochemistry. a. b. + HBr 1. BH 3 •THF 2. H 2 O 2 / - OH c. H + /H 2 SO 4 d. e. 1. Hg(OAc) 2 2. NaBH 4 f. g. h. + i. OsO 4 /H 2 O 2 j. Br OH OH OH HBr/H 2 O 2 D 2 /Pd(C) Br 2 /H 2 O OH OH 1. mCPBA 2. HBr 1. O 3 2. (CH 3 ) 2 S OH
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Br Br Br Br Br Br HO OH HO OH Br 2 p. q. q. (2 ways) + OsO 4 /H 2 O 2 (2 ways) 1. mCPBA 2. H + /H 2 O + OsO 4 /H 2 O 2 OH OH KMnO 4 / - OH (cold, dilute) k. OH OH l. KMnO 4 / - OH (warm, conc) O O 1. mCPBA 2. CH 3 CH 2 OH/H + m. OCH 2 CH 3 HO 1. mCPBA 2. H + /H 2 O k. Br 2 Br 2 n. o. 1. mCPBA 2. H + /H 2 O
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OH Br 2. Show the alkenes produced in this elimination. Indicate which is produced in greatest amount and which in least amount. H 2 SO 4 3. Draw the 5 mono-chloro isomers that are produced upon chlorination of methylcyclohexane. Show the dehydrochlorination products of each. Indicate major and monor products in each reaction. Which alkyl chloride reacts fastest? Which slowest?
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