Exam 2 -- Spring 2009 -- Blank

Exam 2 -- Spring 2009 -- Blank - I. (25 points) Name _ Page...

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Page 1 S09ex2p1 I. (25 points) A. This connectivity represents: (a) (a) Provide the most reasonable curved arrow mechanism expected to occur when 1,4- cyclohexadiene is treated with o n e e q u i v a l e n t of HBr, leading to the product shown. Consider the molecule(s) represented by the following connectivities and check all the statements that are true. 3 or more compounds a pair of diastereomers only a pair of enantiomers only one (unique) compound only chiral compound(s) only at least one meso compound (b) (c) 3 3 B. Achiral product(s) 13 C-NMR: 2 signals achiral compound(s) only This connectivity represents: 3 or more compounds a pair of diastereomers only a pair of enantiomers only one (unique) compound only chiral compound(s) only at least one meso compound achiral compound(s) only 3 This connectivity represents: 3 or more compounds a pair of diastereomers only a pair of enantiomers only one (unique) compound only chiral compound(s) only at least one meso compound achiral compound(s) only H Br 7 (b) Taking into account a l l possible regioisomers and stereoisomers, how many total products will be formed in the reaction detailed above? + Achiral product(s) 13 C-NMR: 4 signals 2 2 + Chiral product(s) 13 C-NMR: 4 signals 2 Starting materials (c) When a second equivalent of HBr is added, a variety of products results, each sharing a molecular formula of C 6 H 10 Br 2 . Draw e a c h and every product that matches the following information, showing stereochemistry clearly when it is present. OH
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Exam 2 -- Spring 2009 -- Blank - I. (25 points) Name _ Page...

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