2004winter-midterm02bsolns

2004winter-midterm02bsolns - 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: 12 H 3 O + , H 2 O OO Write a detailed stepwise mechanism that accounts for the formation of product 2 . (Show all intermediates! Transfer H’s intermolecularly!). 1 H 3 O + , H 2 O Steps 1,2: protonate the carbonyl, deprotonate the α position and generate the conjugated enol form O H H H O H H Steps 3,4: protonate the γ position to form the protonated product, deprotonate the O to give the final product O OH H H OH OH 2 O O H
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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. OCH 3 CH 3 O H 3 CO O CH 3 O OCH 3 OH O O OH O OCH 3 CH 3 O H 3 CO O CH 3 OO H OCH 3 OH HO O OH OH O OH HO HO O OH OH OH O 5% HCl, H 2 O (c) (b) (a) H 2 O, H O O HO O OH H O O HO 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 EtO O OEt O N Li + HO HO O O OH O O OEt O O OEt O HO O O OH HO O O OH O OEt O O (f) (e) (d) LDA = 2. CH 3 CH 2 Br 2.
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2004winter-midterm02bsolns - Name: _KEY_ ID# _ 03-02-04 1....

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