{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

2004winter-midterm02bsolns

2004winter-midterm02bsolns - Name_KEY ID 1 Treatment of...

Info icon This preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Name: ______ KEY _______________ ID# _________________ 03-02-04 2 1. Treatment of ketone 1 with dilute acid leads to its isomerization to ketone 2 as shown: 1 2 H 3 O + , H 2 O O O 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
Image of page 1

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
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 O OH 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
Image of page 2
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.
Image of page 3

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}