Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 23, Problem 36P
Co2+ catalyzes the hydrolysis of the lactam shown here. Propose a mechanism for the metal-ion catalyzed reaction.
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Draw the mechanism for acid-catalyzed ester hydrolysis.
Co2+ catalyzes the hydrolysis of the lactam shown here. Propose a mechanism for the metal-ion catalyzed reaction.
The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures.
Ph
Ph
`N'
`N'
ČH3
ČH3
Methsuximide
Ethosuximide
Phensuximide
Following is a synthesis of phensuximide.
CN
Ph
CN
Ph
CN
1. NaOH, H2O
2. HC, Н20
NaOEt
KCN
Ph-CHO
cOOEt
H
cOOEt
NC
COOEt
3. Нeat
Ethyl
cyanoacetate
(A)
(B)
Benzaldehyde
Ph
Ph
Ph
CH;NH2
НООС
СООН
Et0oC
COOEt
`N'
(C)
(D)
ČH3
Phensuximide
Methsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis of
methsuximide.
Chapter 23 Solutions
Organic Chemistry
Ch. 23.2 - Compare each of the mechanisms listed here with...Ch. 23.2 - Prob. 3PCh. 23.2 - Prob. 4PCh. 23.3 - a. Draw the mechanism for the following reaction...Ch. 23.5 - Prob. 7PCh. 23.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 23.6 - Prob. 9PCh. 23.7 - Prob. 10PCh. 23.7 - Prob. 12PCh. 23.7 - Prob. 13P
Ch. 23.9 - Which of the following amino acid side chains can...Ch. 23.9 - Which of the following C-terminal peptide bonds is...Ch. 23.9 - Carboxypeptidase A has esterase activity as well...Ch. 23.9 - Arginine and lysine side chains fit into trypsins...Ch. 23.9 - Explain why serine proteases do not catalyze...Ch. 23.10 - If H2 18O is used in the hydrolysis reaction...Ch. 23.10 - When apples that have been cut are exposed to...Ch. 23.11 - Prob. 22PCh. 23.11 - The pHactivity profile for glucose-6-phosphate...Ch. 23.11 - Draw the pH-activity profile for an enzyme that...Ch. 23.12 - Prob. 25PCh. 23.12 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 23.12 - What advantage does the enzyme gain by forming an...Ch. 23.12 - Prob. 28PCh. 23.12 - Aldolase shows no activity if it is incubated with...Ch. 23 - Which of the following parameters would be...Ch. 23 - Prob. 30PCh. 23 - Prob. 31PCh. 23 - Prob. 32PCh. 23 - Indicate the type of catalysis that is occurring...Ch. 23 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 23 - Prob. 35PCh. 23 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 23 - there are two kinds of aldolases. Class I...Ch. 23 - Prob. 38PCh. 23 - The hydrolysis of the ester shown here is...Ch. 23 - Prob. 40PCh. 23 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 23 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 23 - Proof that an imine was formed between aldolase...Ch. 23 - Prob. 44PCh. 23 - a. Explain why the alkyl halide shown here reacts...Ch. 23 - Triosephosphate isomerase (TIM) catalyzes the...
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