2004spring-midterm01asolns

2004spring-midterm01asolns - S04 140C 1st Midterm Ver. 1...

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S04 140C 1st Midterm Ver. 1 KEY 04-20-04 2 1. Treatment of the chiral ketone 1 with NaOD in D 2 O gives a racemic mixture of the deuterated ketones 2 and 3 : O 1 H NaOD, D 2 O O 2 D 3 O D . Write a detailed stepwise mechanism that accounts for the formation of 2 and 3 . O H O D D O D OD O O D D O D 2 3 1 Planar enolate anion Protonation above the plane Protonation below the plane
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S04 140C 1st Midterm Ver. 1 KEY 04-20-04 3 2. For each one of the following reactions, circle the product that is formed. O H O HO O H O H O H O OH H O H OH HO O (b) (c) (a) (d) NaOH, H 2 O 5 0 C H 3 O + , H 2 O O 1. (CH 3 ) 3 CO K , (CH 3 ) 3 COH, 2. CH 3 I O O OH 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 Vollhardt, page 789 Vollhardt, page 796 Vollhardt, 18-7
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S04 140C 1st Midterm Ver. 1 KEY 04-20-04 4 H NO OO HCl, H 2 O, CH 3 OH, H + OOO CH 3 CH 2 OH O O CN CN HO CO 2 H OCH 3 CH 3 O O OH H 2 N OCH 2 CH 3 HO O OCH 2 CH 3 CH 3 CH 2 O O OCH 3 HO O O H 3 N CO 2 H O O OCH 2 CH 3 CH 3 CH 2 O O OH Cl H 3 N O OCH 3 CH 3 O HO CO 2 H CO 2 H (f) (g) (e) HCl, H 2 O,
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This note was uploaded on 10/25/2008 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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2004spring-midterm01asolns - S04 140C 1st Midterm Ver. 1...

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