HW18Key - alcohol Your mechanism should account for the...

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Graded Homework Problem #18 – Answer Key This problem is worth a total of 20 raw points. When ( S )-3-bromo-2,3-dimethylpentane (shown below) is dissolved in H 2 O/acetone, the resulting solution is optically active . When this solution is heated to 60°C, the alkyl bromide disappears, and a mixture of products is formed. This product mixture is optically inactive . One of the products isolated (as a racemic mixture) is an alcohol having the molecular formula C 7 H 16 O. Using curved arrows to show movement of electron pairs, propose a mechanism to account for formation of this
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Unformatted text preview: alcohol. Your mechanism should account for the fact that this product is formed as a racemic mixture!!! he racemic alcohol forms via an S N 1 reaction mechanism. Racemization occurs because H 2 O can react with equal likelihood from either side of the planar carbocation intermediate: H 3 C H 3 C H Br ( S )-3-Bromo-2,3-dimethylpentane H 2 O/acetone C 7 H 16 O (racemic) H 3 C H 3 C H Br H 3 C H CH 3 (planar carbocation) O H H from "bottom" from "top" H 3 C H 3 C H O H H O H H H 3 C H 3 C H OH O H H H H 3 C H CH 3 O H H O H H H 3 C H CH 3 HO O H H H Br...
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This note was uploaded on 07/16/2008 for the course CH 310M taught by Professor Iverson during the Spring '05 term at University of Texas.

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