ps5 (1) - Massachusetts Institute of Technology 5.13:...

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Massachusetts Institute of Technology 5.13: Organic Chemistry II Fall 2003, S. Tabacco Problem Set 5 Due: Thursday, 11/6/03 at 4 PM 1. a) The Cope elimination generally provides the least substituted alkene product. Analyze the selectivity of the following reaction in the same way that we analyzed the selectivity of the Hofmann elimination in lecture. Provide an explanation for the observed selectivity. Me Me N H 2 O 2 Me Me H 2 C H 3 C Me Me Me Me Me major minor b) While the Cope elimination is a good way to convert an amine N -oxide to an alkene and a hydroxylamine, in some cases the reverse Cope elimination can be used to convert an alkene to an amine N -oxide. Using what you know about the mechanism for the Cope elimination, propose a mechanism for the following reverse Cope elimination. OH CHCl 3 O Me N Me H 2 C N Me 60 °C 2. Provide a synthesis that will selectively generate each of the following molecules from the given starting material. Show all of the key intermediates and reagents.
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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ps5 (1) - Massachusetts Institute of Technology 5.13:...

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