2004spring-midterm02bsolns

2004spring-midterm02bsolns - Name: _ ID# _ 05-18-04 1. Upon...

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Name: ________________________ ID# _________________ 05-18-04 2 1. Upon treatment of the ketoester 1 with sodium ethoxide in ethanol, followed by a mild acidic workup, the isomeric product 2 is obtained: O OCH 2 CH 3 O O OCH 2 CH 3 O 1 . 1. CH 3 CH 2 O Na + , CH 3 CH 2 OH 2. H + , H 2 O 2 . Write a detailed , arrow-pushing, stepwise mechanism that accounts for this transformation. 4 4 4 Note : Show all intermediates! Transfer H’s intermolecularly! CH 3 O O OCH 3 O OCH 3 O H 3 CO O H H H 3 CO OO H H 3 CO O O H O H H CH 3 O CH 3 O O OCH 3 O H 3 CO H 3 CO H 3 CO OCH 3 O H 3 CO O O OCH 3 O CH 3 O H OCH 3 O H 3 CO O OCH 3 O H 3 CO O O H 3 CO O OCH 3 1 2 Product of step 1 2. H + , H 2 O
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Name: ________________________ ID# _________________ 05-18-04 3 2. For each one of the following reactions, circle the product that is formed. OCH 2 CH 3 O O H O H O N 3 HO H NH 2 O OEt O O EtO O OEt HO O O OH O O N O O HO O O OH HO O O OH O O OCH 3 O OH N 3 (a) 1. CH 3 CH 2 O Na + , CH 3 CH 2 OH 2. H 3 O + , H 2 O (c) H 2 , Pd/C (b) 2. 3. HCl, H 2 O, 1. EtO Na +
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Name: ________________________ ID# _________________ 05-18-04 4 H 3 CH 2 CO O OCH 2 CH 3 O N MeO O O OMe O O 1. MeO Na + , MeOH 2. CH 3 CH 2 Br 3. HCl , H 2 O, Cl Cl O OMe H 3 N O OH H 3 N Cl O OH H 3 N O O OCH 2 CH 3 O O OCH 2
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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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2004spring-midterm02bsolns - Name: _ ID# _ 05-18-04 1. Upon...

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