HW18 - CH 310M/318M Spring 2008 Dr Bocknack Last Name First...

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CH 310M/318M Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Please circle the section in which you are registered ! POINTS MAY BE DEDUCTED IF YOU DON’T ! MWF 9:00 TTh 8:00 Graded Homework Problem #18 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
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