Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 22, Problem 38P
The hydrolysis of the ester shown here is catalyzed by morpholine. Propose a mechanism for the reaction, (Hint: The pKa of the conjugate acid of morpholine is 9.3. so morpholine is too weak a base to function as a base catalyst.)
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When 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.
Draw a mechanism for the following acid catalysed hydrolysis reaction. Explain verbally within your group
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MeO
Me
OMe
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Me
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Propose a mechanism for the reaction of glucosamine with acetylacetone to form product containing the pyrrole ring.
Hint: The likely first step involves attack of the nucleophilic amino group of glucosamine on one of the carbonyl carbons of acetylacetone and leads to formation of an aminoalcohol. This can dehydrate to form a α,β unsaturated carbonyl compound. The alkene can then react with the aldehyde to form a ring structure.
Chapter 22 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 22.2 - Compare each of the mechanisms listed here with...Ch. 22.2 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.3 - a. Draw the mechanism for the following reaction...Ch. 22.5 - Prob. 7PCh. 22.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 22.6 - Prob. 9PCh. 22.7 - Prob. 10PCh. 22.7 - Prob. 12PCh. 22.7 - Prob. 13P
Ch. 22.9 - Which of the following amino acid side chains can...Ch. 22.9 - Which of the following C-terminal peptide bonds is...Ch. 22.9 - Carboxypeptidase A has esterase activity as well...Ch. 22.10 - Arginine and lysine side chains fit into trypsins...Ch. 22.10 - Explain why serine proteases do not catalyze...Ch. 22.11 - If H2 18O is used in the hydrolysis reaction...Ch. 22.11 - Draw the pH-activity profile for an enzyme that...Ch. 22.12 - The pHactivity profile for glucose-6-phosphate...Ch. 22.12 - Prob. 23PCh. 22.13 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 22.13 - What advantage does the enzyme gain by forming an...Ch. 22.13 - Prob. 26PCh. 22.13 - Prob. 27PCh. 22.13 - Aldolase shows no activity if it is incubated with...Ch. 22 - Which of the following parameters would be...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Indicate the type of catalysis that is occurring...Ch. 22 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 22 - Prob. 34PCh. 22 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 22 - there are two kinds of aldolases. Class I...Ch. 22 - Prob. 37PCh. 22 - The hydrolysis of the ester shown here is...Ch. 22 - Prob. 39PCh. 22 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 22 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 22 - Proof that an imine was formed between aldolase...Ch. 22 - Prob. 43PCh. 22 - a. Explain why the alkyl halide shown here reacts...Ch. 22 - Triosephosphate isomerase (TIM) catalyzes the...
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