Barbiturates are prepared by treating a derivative of diethyl malonate with urea in the presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate and urea. -OEt H,N -NH 1. EtO-Na+ + 2 ELOH 2. Н,О -OEt H,N -NH Diethyl diethylmalonate Urea 5,5-Diethylbarbituric acid (Barbital) Barbital is prescribed under one of a dozen or more trade names.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
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The pKa of barbital is 7.4. Which is the most acidic hydrogen in this molecule? How do you account for its acidity?

Barbiturates are prepared by treating a derivative of diethyl malonate with urea in the
presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of
barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate and urea.
-OEt
H,N
-NH
1. EtO-Na+
+ 2 ELOH
2. Н,О
-OEt
H,N
-NH
Diethyl
diethylmalonate
Urea
5,5-Diethylbarbituric acid
(Barbital)
Barbital is prescribed under one of a dozen or more trade names.
Transcribed Image Text:Barbiturates are prepared by treating a derivative of diethyl malonate with urea in the presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate and urea. -OEt H,N -NH 1. EtO-Na+ + 2 ELOH 2. Н,О -OEt H,N -NH Diethyl diethylmalonate Urea 5,5-Diethylbarbituric acid (Barbital) Barbital is prescribed under one of a dozen or more trade names.
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