Problem_Set_5A_solutions - Chem 3580 - Spring 2009 Problem...

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Chem 3580 - Spring 2009 Problem Set #5A - Solutions 1. The mechanism below explains the incorporation of the label in the first case. O O H OH 2 O O H O O H H O H 18 H H 18 H O H 18 O H 18 18 In the second case, the loss of some of the optical activity suggests some racemization. This can be explained by the formation of a planar carbocation (path (a) below. The change in configuration to R suggests inversion. This can be explained by S N 2 type reaction at the asymmetric carbon (path (b). It seems both processes are occurring simultaneously. O H OH 2 O H O O H H O H O O O H H H HO HO Racemic O O H R)-3,7-dimethyl-3-octanol H O H Backside attack S N 2 S N 1 (a) (b) path (a) path (b) H O H water attack followed by proton transfer to water 2. Supply the missing reagents and reaction conditions (a) — (d) for each transformation and write down the structure of A. OH CO 2 CH 3 O O OH OH O OH O COOH O CO 2 CH 3 (a) LiAlH 4 (reducing agent) (c) (d) (b) A (a) Catalytic HCl, heat (intramolecular transesterification).
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Problem_Set_5A_solutions - Chem 3580 - Spring 2009 Problem...

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