Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 23.7, Problem 12P
Interpretation Introduction

Interpretation: The reason why nitro group changes the relative leaving tendencies of carboxy and 2,4dinitrophenoxy group in the tetrahedral intermediate has to be explained.

Concept introduction:

  • Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.
  • Base Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the removal of a proton. There are two types of catalysis:
  1. 1. Specific-base catalysis: Proton is completely removed before the slow step in a reaction
  2. 2. General- base catalysis: Proton is completely removed during the slow step in a reaction
  • Nucleophilic catalysis: A catalysis which takes place due to the formation of a covalent bond by a nucleophile with one of the reactants.

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Based on the reaction mechanism of the following reaction, provide an explanation for the role of concentrated HCl in the work-up process(it plays more than one role)
Why do the nitro groups change the relative leaving tendencies of the carboxy and 2,4-dinitrophenoxy groups in the tetrahedral intermediate?
7. The rate constant for the hydrolysis of a m-chloro substituted and p-methoxy substituted organic substance are 0.50 and 0.015 at 25 °C, respectively. The o values of m-Cl and p-OMe are +0.37 and -0.27, respectively. Calculate the reaction constantp and rate constant for hydrolysis of unsubsituted substance and p-nitro (6 = + 0.75) substituted substance.

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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