HWKey (19) - all important reaction intermediates If a...

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Problem of the Day #18 – Answer Key Deadline : 3:00 p.m., Tuesday, 7/8/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When enantiomerically pure ( S )-3-bromo-2- methylpentane is heated to 60°C in a mixture of H 2 O/acetone, 2-methyl-2-pentanol (achiral) is eventually isolated as the major organic product. This overall transformation is shown below: Br ( S )-3-Bromo-2-methylpentane H 2 O/acetone 60°C OH + H 3 O + Br 2-Methyl-2-pentanol (a) (15 points) Propose a reaction mechanism to account for the overall transformation shown above. As usual, use curved arrows to show movement of electron pairs, and be sure to show structures of
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Unformatted text preview: all important reaction intermediates. If a reaction intermediate is a resonance hybrid, it is only necessary to draw the most important contributing resonance structure. [ Note : The acetone is necessary to dissolve the alkyl bromide starting material. Acetone DOES NOT play any role whatsoever in the reaction mechanism!!!] (b) (5 points) Is the mechanism you proposed above best described as an example of an S N 1 reaction, or is it an example of an S N 2 reaction? Circle your choice below. No additional explanation is required. S N 1 S N 2 Br H Br (hydride shift) H O H H O H H Br O H H OH O H H H Br Br...
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