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. O O HO O H O H O H O OH O H OH HO O (b) (c) (a) (d) NaOH, H 2 O 5 0 C NaOH, H 2 O O 1. CH 3 CH 2 O Na , CH 3 CH 2 OH, -5 o C O 2. NaOH, H 2 O, ! O O O O O O O O 1. [(CH 3 ) 2 CH] 2 N Li , " 78 o C 2. CH 3 I O O O
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Name: ________________________ ID# _________________ 04-19-05 4 NH O HCl, H 2 O, ! O CN CO 2 H OH H 2 N H 3 N O O (f) (g) (e) HCl, H 2 O, ! (h) O O CO 2 H CO 2 H O CO 2 H O O CO 2 H CO 2 H CO 2 H O O O CH 3 OH HO O OCH 3 O OCH 3 O OCH 3 CH 3 O O O O Cl H 3 N O OH O O CH 3 OH, H + O O OCH 3 CH 3 O O OCH 3 HO O OCH 3 CH 3 O HO 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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