Exam2Key - I. (25 points) Name _ Page 1 S09ex2p1 A....

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Name _______________________ 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) x x 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 x x 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 x x achiral compound(s) only H Br note: H is now on the end - may be drawn in Br 7 2 pts/ per step 3 pts for intermediate (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 Br Br Br Br Br Br Br Br Br Br Br two - only stereoisomers there are no regioisomeric products 3
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Name _______________________ Page 2 S09ex2p2 II. (25 points) Cyclopropyl groups are extremely useful in organic syntheses, but much of their reactivity and conformational stability depends on how they are connected to other
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Exam2Key - I. (25 points) Name _ Page 1 S09ex2p1 A....

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