2005spring-midterm01bsolns

2005spring-midterm01 - Name ID 1 Treatment of the chiral ketone 1 with 18O labeled water under acidic conditions gives a racemic mixture of the

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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 3 H 2 18 O H . Write a detailed stepwise mechanism that accounts for the formation of 2 and 3 . Two unrealetd events take place: 1. Oxygen exchange via the hydrate 2. Racemization of the a position via the enol. O 1 H . H O H H OH H . H O H OH H . H O H H O H OH H . O H OH 2 H H O H O H H O H H . H O H O H . Planar enol H O H H H O H H O H H . O H 3 H 2 O H . O H O H H O H H 18 O H H O H H =
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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 O O O 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 OH O OH O 1. [(CH 3 ) 2 CH] 2 N Li , ² 78 o C 2. CH 3 I O O O
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Name: ________________________ ID# _________________ 04-19-05 4 O CN CO 2 H (f) (g) (e) HCl, H 2 O, ± (h) O O CO 2 H HO 2 C O CO 2 H O O CO 2 H CO 2 H HO 2 C OO CH 3 OH, H + H 3 CO O OCH 3 H 3 CO O OCH 3 OCH 3 HO O O CH 3 OH OCH 3 CH 3 O O OCH
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This note was uploaded on 04/14/2009 for the course CHEM140C 234234 taught by Professor Nefzi during the Spring '09 term at UCSD.

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2005spring-midterm01 - Name ID 1 Treatment of the chiral ketone 1 with 18O labeled water under acidic conditions gives a racemic mixture of the

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