Barbiturates are prepared by treatment of diethyl malonate or 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 an urea. Barbital is prescribed under one of a dozen or more trade names. Propose a mechanism for This reactionThe pKa of barbital is 7.4. Which is the most acidic hydrogen in this molecule and how do you account for its acidity? H,NNHCOC,H;C.C,H5.1. C,H,O¯N *2. H,09.2)\4.C=0O + 2C,H;OHC,H,NHC,H;COC,H,H,N5,5-Diethylbarbituric acid(Barbital)Diethyl diethylmalonateUrea(a) Propose a mechanism for this reaction.(b) The pK, of barbital is 7.4. Which is the most acidic hydrogen in this molecule and how doyou account for its acidity?

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Answered: H,N NH COC,H; C. C,H5. 1. C,H,O¯N * 2.…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Barbiturates are prepared by treatment of diethyl malonate or 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 an urea. Barbital is prescribed under one of a dozen or more trade names.

Propose a mechanism for This reaction
The pKa of barbital is 7.4. Which is the most acidic hydrogen in this molecule and how do you account for its acidity?

H,N
NH
COC,H;
C.
C,H5.
1. C,H,O¯N *
2. H,0
9.
2)
\4.
C=0
O + 2C,H;OH
C,H,
NH
C,H;
COC,H,
H,N
5,5-Diethylbarbituric acid
(Barbital)
Diethyl diethylmalonate
Urea
(a) Propose a mechanism for this reaction.
(b) The pK, of barbital is 7.4. Which is the most acidic hydrogen in this molecule and how do
you account for its acidity?

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