Orgo workshop 3-29 - Practice problems and course slides w/ notes PDF

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Practice problems and course slides w/ notes...

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CHEMISTRY 242, Spring 2020, Percec

ORGANIC CHEMISTRY WORKSHOP Problem Set VII 1. Provide the structures for the major product(s) of the following reactions.

2. Propose a plausible mechanism for the following reaction. Provide the structures of all intermediates and make sure you show every step in the mechanism using the arrow-pushing formalism.

3. Whenever the Hofmann elimination is attempted on an amine containing a hydroxyl group on the β  -carbon,  an epoxide is produced instead of an alkene (see example below).

A. Propose a reasonable mechanism to explain this observation. B. Pseudoephedrine, structure A, is a decongestant used in over-the-counter cold remedies. When pseudoephedrine is subjected to the conditions of the Hofmann elimination, the product is stereoisomer B. From this result deduce the precise stereochemistry of pseudoephedrine and present your answer as a drawing of the structure using wedges and dashes to show stereochemistry....