0243Pb36an-09

0243Pb36an-09 - 8 H 16 O In this case addition of water to...

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Answers to Problem 36, Chemistry 0243, 2009 (a) Write a perfect arrow formalism mechanism for the reaction of cyclohexene ( 1 ) with H 2 O/H 3 O + to give cyclohexanol, 3. H H H 2 O/H 3 O + 1 3 C 6 H 12 O H H 1 H O H H + H H H + H O H H H H O H H + H O H H H H O H 3 C 6 H 12 O
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(b) 1,2-Dimethylcyclohexene ( 2 ) under the same conditions leads to two isomeric products. Use your mechanism from part (a) to draw structures for the two products, 4 and 5 , and explain why there are two. CH 3 CH 3 H 2 O/H 3 O + 2 4 + 5 each C
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Unformatted text preview: 8 H 16 O In this case, addition of water to the carbocation intermediate can occur in two ways: from the same side as the methyl group or from the opposite side. Deprotonation gives the cis/trans pair, 4 and 5 . CH 3 CH 3 2 H O H H + CH 3 CH 3 H + CH 3 H CH 3 + = 1. add from top 2. deprotonate 1. add from bottom 2. deprotonate CH 3 H CH 3 CH 3 H CH 3 OH OH 4 and 5...
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Fall '10 term at NYU.

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0243Pb36an-09 - 8 H 16 O In this case addition of water to...

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