3) a. Testosterone is one of the most important male steroid hormones. When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a mechanism to account for this reaction. CH3OH H H A H H H H HO H Testosterone b. Starting from testosterone, how would you prepare the following substance? CH3 O CH3OH H CH3 0 H H H H3O+ B H H H H H H CH3 HO H H D CH3OH H H

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
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3) a. Testosterone is one of the most important male steroid hormones. When testosterone is
dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a
mechanism to account for this reaction.
CH3OH
H
Testosterone
HO
H
H3O+
H
H
H
b. Starting from testosterone, how would you prepare the following substance?
CH3 O
CH3OH
CH3 O
H
H
CUP AP A
H
H H
H H
H
A
B
CH3
HO
H
H
D
CH3 OH
H
H
Transcribed Image Text:3) a. Testosterone is one of the most important male steroid hormones. When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a mechanism to account for this reaction. CH3OH H Testosterone HO H H3O+ H H H b. Starting from testosterone, how would you prepare the following substance? CH3 O CH3OH CH3 O H H CUP AP A H H H H H H A B CH3 HO H H D CH3 OH H H
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