2004spring-midterm01bsolns

2004spring-midterm01bsolns - S04 140C 1st Midterm Ver. 2...

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S04 140C 1st Midterm Ver. 2 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 . See ver. 1 for mechanism!
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S04 140C 1st Midterm Ver. 2 KEY 04-20-04 3 2. For each one of the following reactions, circle the product that is formed. O H O HO O O O O OH H O 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 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 O Vollhardt, p. 789 Vollhardt 18-7 Vollhardt page 796
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S04 140C 1st Midterm Ver. 2 KEY 04-20-04 4 OO OOO H NO O OC N CH 3 CH 2 OH, H + CH 3 OH HCl, H 2 O, OCH 2 CH 3 CH 3 CH 2 O HO CO 2 H CN H 2 N O OH OCH 3 CH 3 O O OCH 2 CH 3 HO O OCH 3 CH 3 O O O 2 H O OH Cl H 3 N O OCH 2 CH 3 CH 3 CH 2 O OCH 3 HO H 3 N O O HO CO 2 H CO 2 H (f) (g) (e) (h) HCl, H 2 O, Vollhardt, 883 Vollhardt, p. 873,4 Vollhardt, p. 876, 891-2 Vollhardt, p. 877
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S04 140C 1st Midterm Ver. 2 KEY 04-20-04 5 3. For each of the following pairs of compounds, decide which one is more acidic, and
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2004spring-midterm01bsolns - S04 140C 1st Midterm Ver. 2...

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