2004winter-midterm02asolns

2004winter-midterm02asolns - Name: _KEY_ ID# _ 03-02-04 1....

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Name: ______ KEY _______________ ID# _________________ 03-02-04 2 1. Treatment of ketone 1 with dilute acid leads to its isomerization to ketone 2 as shown: OO 12 H 3 O + , H 2 O Write a detailed stepwise mechanism that accounts for the formation of product 2 . (Show all intermediates! Transfer H’s intermolecularly!). O 2 O 1 H 3 O + , H 2 O OH H H OH Steps 1,2: protonate the carbonyl, deprotonate the α position and generate the conjugated enol form OH O H H H O O H H H Steps 3,4: protonate the γ position to form the protonated product, deprotonate the O to give the final product
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Name: ______ KEY _______________ ID# _________________ 03-02-04 3 2. For each one of the following reactions, circle the product that is formed. H O O OCH 3 CH 3 O H 3 CO O CH 3 O OCH 3 OH O O OH O HO O OCH 3 CH 3 O H 3 CO O CH 3 OO H OCH 3 OH HO O OH OH O OH H O OH HO HO O OH OH OH O O HO 5% HCl, H 2 O (c) (b) (a) H 2 O, NaOH, H 2 O 5 0 C
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Name: ______ KEY _______________ ID# _________________ 03-02-04 4 O OCH 3 O O H 3 CO O OCH 3 H 3 CO O OCH 3 O N Li + O HO O O OH O O OCH 3 O O OCH 3 O HO O O OH HO O O OH HO O OCH 3 O (f) (e) (d) LDA = 2. CH 3 Br 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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2004winter-midterm02asolns - Name: _KEY_ ID# _ 03-02-04 1....

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