Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321918765
Author: Bruice
Publisher: PEARSON EDUCATION (COLLEGE)
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Chapter 23.7, Problem 13P
Interpretation Introduction

Interpretation: The result of 18O labelled water hydrolysis of aspirin when the ortho-carboxy substituent acts as an intramolecular general-base catalyst and as an intramolecular nucleophilic catalyst has to be given.

Concept introduction:

Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.

Intramolecular catalysis: A catalysis where catalyst is a part of the molecule that undergoes the reaction promotes the reaction in a species.

Intramolecular nucleophilic catalysis: A catalysis where catalyst is a part of the molecule that undergoes the reaction promotes the reaction in a species by acting as a nucleophile.

Intramolecular general-base catalysis: A catalysis where catalyst is a part of the molecule that undergoes the reaction promotes the reaction in a species by completely removing a proton during the slow step in a reaction.

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Whether the ortho-carboxy substituent acts as an intramolecular general-base catalyst or as an intramolecular nucleophilic catalyst can be determined by carrying out the hydrolysis of aspirin with 18O-labeled water and determining whether 18O is incorporated into ortho-carboxy-substituted phenol. Explain the results that would be obtained with the two types of catalysis.
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Chapter 23 Solutions

Organic Chemistry

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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