exam 2 W09-1 - Name _______________________ Page 1 w09ex2p1...

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Unformatted text preview: Name _______________________ Page 1 w09ex2p1 I. (25 points) A. This connectivity represents: (a) (a) When dienes are treated with o n e e q u i v a l e n t of HBr, a variety of addition products form. Provide the most reasonable two-step curved arrow mechanism for the production of P1. 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 a pair of enantiomers one (unique) compound chiral compound(s) only at least one meso compound (b) (c) x x 3 3 B. Unique connectivity 13 C-NMR: 4 signals 1 H-NMR ratio of 6:2:1 I achiral compound(s) only This connectivity represents: 3 or more compounds a pair of diastereomers a pair of enantiomers one (unique) compound 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 a pair of enantiomers one (unique) compound chiral compound(s) only at least one meso compound x x achiral compound(s) only OH OH Cl O O Br H Br note: H is now on the end - may be drawn in Br 6 2 pts/ per step 2 pts for intermediate (b) Several different alkene products, regioisomers of P1 above, are produced in varying quantities from the starting materials shown above. Draw the product (connectivity only) that matches the data. Br Br Br + Racemic mixture 13 C-NMR: 5 signals 1 H-NMR ratio of 3:3:2:1 Unique connectivity 13 C-NMR: 5 signals 1 H-NMR ratio 3:2:2:2 2 2 2 + + Br Racemic mixture 13 C-NMR: 5 signals 1 H-NMR ratio 3:2:2:1:1 2 Product P1 Starting materials Product P2 Product P3 Product P4 Product P5 (c) P1 is the major product observed in this reaction. Explain this regioselection briefly. 2 tertiary C+ AND resonance stabilization BOTH explanations must be noted Name _______________________ Page 2 W09ex2p2 II. (21 points) The asthma medication Albuterol is sold as a stereoisomeric mixture, and one of its components is shown below. Conformational analysis can be done on many of the bonds in this compound, but we will only look at one....
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exam 2 W09-1 - Name _______________________ Page 1 w09ex2p1...

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