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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Co2+ catalyzes the hydrolysis of the lactam shown here. Propose a mechanism for the metal-ion catalyzed reaction.
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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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- 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.arrow_forwardRank the attached compounds in order of increasing basicity andexplain the order you chose.arrow_forwardIf a lactam (cyclic amide) contains an alkyl group with an amino group, treatment with lithium diisopropyl amide (LDA) results in a ring-expanded lactam, as shown here. Provide a detailed mechanism for this reaction.arrow_forward
- Identify one substrate and one reagent that could be combined to make the completed product.arrow_forwardNaturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.arrow_forwardWhen cyclohexanone is heated in the presence of a large amount of acetone cyanohydrin and a small amount of base, cyclohexanone cyanohydrin and acetone are formed. Propose a mechanism.arrow_forward
- See image belowarrow_forwardWhen an α-hydroxy amide is treated with Br2 in aqueous NaOH under Hofmann rearrangement conditions, loss of CO2 occurs and a chain-shortened aldehyde is formed. The mechanism involves the following steps: Base abstracts an acidic amide proton, yielding amide anion 1; The amide anion reacts with bromine in an α-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion 3; Rearrangement occurs to yield isocyanate 4; Water adds to the isocyanate to yield carbamic acid 5; Elimination of CO2 yields carbinolamine 6; Following proton transfer, expulsion of ammonia yields the final product aldehyde. Write out the mechanism and then draw the structures of bromoamide anion 3 and amide anion 1.arrow_forwardEthanolamine ammonia lyase, a coenzyme B12–requiring enzyme, catalyzes the following reaction. Propose a mechanism for this reaction.arrow_forward
- a OH CH2CNHCH3 T CH3 d OH CHCHNHCH3 CH3 Ephedrine can be synthesized via reductive amination plus other necessary reactions. Predict the necessary reactants and reagents that will give the intermediate and final products shown.arrow_forwardThe mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.arrow_forwardPlease answer this question correctly please.arrow_forward
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