Ph Ph CH3 ČH3 Methsuximide Ethosuximide Phensuximide (racemic) (racemic) (racemic) Following is a synthesis of phensuximide. CN Ph CHO + Ph KCN Ph CN CN NaOEt 1. NaOH, H,O H NÓ 2. НС, Н,о COOE 3. heat COOEt COOEL Benzal- Ethyl dehyde cyanoacetate (A) (В) (гасеmie) Ph Ph Ph CH,NH HOOC СООН ELOOC COOEt 'N' (C) (racemic) (D) (racemic) ČH3 Phensuximide (racemic)

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter31: Immunochemistry
Section: Chapter Questions
Problem 31.75P
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The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures.

Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?

Ph
Ph
CH3
ČH3
Methsuximide
Ethosuximide
Phensuximide
(racemic)
(racemic)
(racemic)
Following is a synthesis of phensuximide.
CN
Ph CHO +
Ph
KCN
Ph
CN
CN
NaOEt
1. NaOH, H,O
H
NÓ
2. НС, Н,о
COOE 3. heat
COOEt
COOEL
Benzal-
Ethyl
dehyde cyanoacetate
(A)
(В)
(гасеmie)
Ph
Ph
Ph
CH,NH
HOOC
СООН
ELOOC
COOEt
'N'
(C)
(racemic)
(D)
(racemic)
ČH3
Phensuximide
(racemic)
Transcribed Image Text:Ph Ph CH3 ČH3 Methsuximide Ethosuximide Phensuximide (racemic) (racemic) (racemic) Following is a synthesis of phensuximide. CN Ph CHO + Ph KCN Ph CN CN NaOEt 1. NaOH, H,O H NÓ 2. НС, Н,о COOE 3. heat COOEt COOEL Benzal- Ethyl dehyde cyanoacetate (A) (В) (гасеmie) Ph Ph Ph CH,NH HOOC СООН ELOOC COOEt 'N' (C) (racemic) (D) (racemic) ČH3 Phensuximide (racemic)
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