Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
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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Which of the following bases is strong enough to deprotonate N,Ndimethylacetamide [CH3CON(CH3)2, pKa = 30], so that equilibrium favors the products:
(a) NaNH2; (b) NaOH?
What is the conjugate acid of acetamide and its pka value?
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.
Chapter 22 Solutions
Organic Chemistry (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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