Graded Homework Problem #18 – Answer Key Deadline : 3:00 p.m., Thursday, 4/24/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! When enantiomerically pure (R)-3-methyl-3-hexanol is exposed to HBr, a racemic mixture of 3-bromo-3-methylhexane can eventually be isolated. Water forms as a byproduct of this reaction. This overall transformation is shown below: HO CH 3 ( R )-3-Methyl-3-hexanol H Br Br CH 3 + H 3 C Br + H 2 O ( R )-3-Bromo-3-methylhexane (50%) ( S )-3-Bromo-3-methylhexane (50%) (a) Propose a reaction mechanism to account for formation of both enantiomers of the alkyl halide product. As usual, use curved arrows to show movement of electron pairs, and be sure to show structures of all important reaction intermediates. If a reaction intermediate is a resonance hybrid, it
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