2005spring-midterm01-KEY

2005spring-midterm01-KEY - Name: _ ID# _ 04-19-05 1....

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Name: ________________________ ID# _________________ 04-19-05 2 1. Treatment of the chiral ketone 1 with 18 O labeled water under acidic conditions gives a racemic mixture of the labeled ketones 2 and 3 : O 1 H H 2 18 O , H 3 18 O + 18 O 2 H 3 18 O H . Write a detailed stepwise mechanism that accounts for the formation of 2 and 3 .
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Name: ________________________ ID# _________________ 04-19-05 3 2. For each one of the following reactions, circle the product that is formed. ! ! "! ! " ! " ! " ! !" ! " !" "! ! #$% #’% #(% )’!"* " , ! - . / )’!"* " , ! ! 01 /" 2 /" , ! )’ * /" 2 /" , !"* 3- 4 / ! ,1 )’!"* " , !* ! ! ! ! ! ! ! ! ! 01 5#/" 2 % , /"6 , ) 78 * " 9: 4 / ,1 /" 2 ; ! ! !
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ID# _________________ 04-19-05 4 !H O ( ! O C! CO ( H OH H ( ! H 3 ! O O *+, *-, *., ( ! */, O O CO ( H CO ( H O CO ( H O O CO ( H CO ( H CO ( H O O O CH 3 OH HO O OCH 3 O OCH 3 O OCH 3 CH 3 O O O O C% H 3 ! O
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This note was uploaded on 06/07/2008 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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2005spring-midterm01-KEY - Name: _ ID# _ 04-19-05 1....

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