Problems 031
- Both OH groups of one of the following steroid diols react with excess ethyl chloroformate, but only one OH group of the other
steroid diol reacts under the same conditions:
Explain the difference in reactivity.
- The acid-catalyzed dehydration of an alcohol to a rearranged alkene is known as a Wagner–Meerwein rearrangement. Propose a
mechanism for the following Wagner–Meerwein rearrangement:
- Diethylstilbestrol (DES) was given to pregnant women to prevent miscarriage, until it was found that the drug caused cancer in
both the mothers and their female children. DES has estradiol activity even though it is not a steroid. Draw DES in a way that
shows that it is structurally similar to estradiol.
HO
OH
CH 3 CH 2
CH 2 CH 3
diethylstilbestrol
DES
+ H 3 O+
OH
isoborneol camphene
H+
CH 3 CH 2 OCCl CH 3 CH 2 OCO
O
O
OH
H 3 C
HO
H 3 C
5 -cholestane-3 ,7
H H
OH
-diol
CH 3 CH 2 OCO
CH 3 CH 2 OCCl
O
O O
H
OCOCH 2 CH 3
H 3 C
HO OH
H 3 C
H
5 -cholestane-3 ,7 -diol
