HW14Key - for the reaction shown above. Be sure to show...

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Graded Homework Problem #14 – Answer Key This problem is worth a total of 20 raw points. When 1-methyl-1-vinylcyclopentane is treated with H 2 O in which a catalytic amount of sulfuric acid is dissolved, the major product isolated is 1,2-dimethylcyclohexanol (formed as a mixture of all possible stereoisomers). This overall transformation is shown below: H 2 O, H 2 SO 4 (cat.) OH Using curved arrows to show movement of electron pairs, propose a mechanism
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Unformatted text preview: for the reaction shown above. Be sure to show structures of all important reaction intermediates that form during the course of the reaction! You may assume that H 3 O + is the reactive acid present under these reaction conditions it is not necessary to write a mechanism to explain how H 3 O + is formed! H O H H H O H H (alkyl shift) O H H O H H O H H O H H O H H...
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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 at Austin.

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