2004spring-midterm02asolns

2004spring-midterm02asolns - 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 methoxide in methanol, followed by a mild acidic workup, the isomeric product 2 is obtained: O 1 1. CH 3 O Na + , CH 3 OH . OCH 3 O 2. H + , H 2 O O 2 . OCH 3 O Write a detailed , arrow-pushing, stepwise mechanism that accounts for this transformation. 4 4 4 Note : Show all intermediates! Transfer H’s intermolecularly! O OCH 3 O O OCH 3 O H 3 CO OCH 3 O H 3 CO O OCH 3 O H 3 CO O O OCH 3 O CH 3 O H OCH 3 O H 3 CO O H H OCH 3 O H 3 CO O O H 3 CO O OCH 3 H 3 CO OO H H 3 CO H 3 CO O O H O H H H 3 CO 1 2 Product of step 1 2. H + , H 2 O CH 3 O CH 3 O CH 3 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 3 O O H 3 CO H O H O N 3 OCH 3 O O O OCH 3 O OH N 3 O O HO O O OH HO H NH 2 O HO O O OH O O OCH 3 HO O O OH N O O (c) 1. CH 3 O Na + , CH 3 OH 2. H 3 O + , H 2 O (b) H 2 , Pd/C (a) 2. 3. HCl, H 2 O, 1. CH 3 O Na +
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Name: ________________________ ID# _________________ 05-18-04 4 Br N EtO O O OEt O O 1. EtO Na + , EtOH 2. CH 3 CH 2 Br 3. HCl , H 2 O, Cl Cl Cl O OMe H 3 N O OH H 3 N Cl Cl O OH H 3 N Cl (e) (d) 1. KCN, DMSO 2. LiAlH 4 , Et 2 O 3. HCl, H 2 O
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This note was uploaded on 04/07/2009 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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2004spring-midterm02asolns - Name: _ ID# _ 05-18-04 1. Upon...

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