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? greatest
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This homework help was uploaded on 04/09/2008 for the course CHEM 316 taught by Professor Kantorowski during the Fall '08 term at Cal Poly.

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

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