Pb87, 0243-09

Pb87, 0243-09 - a. The -1,3-dibromocyclopentane formed is...

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Problem 87, Chemistry 0243 - 2009 When ( R )-3-bromocyclopentene ( 1 ) is treated with HBr, trans -1,2- dibromocyclopentane ( 2 ) and cis - and -1,3-dibromocyclopentane ( 3 ) are formed. Br 1 Br Br Br Br -2 racemic -3 HBr Br Br -3 optically active Develop a mechanism and use it to account for the following observations:
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Unformatted text preview: a. The -1,3-dibromocyclopentane formed is optically inactive. b. The -1,3-dibromocyclopentane formed is optically active. c. The -1,2-dibromocyclopentane is formed as a racemic mixture. d. There is no -1,2-dibromocyclopentane formed....
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Fall '10 term at NYU.

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