7th Edition

ISBN: 9780321803221

Author: Paula Y. Bruice

Publisher: Prentice Hall

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Textbook Question

Chapter 16, Problem 94P

Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the direction of the transition state. The synthesis of the antibody is carried out in the presence of a transition state analog—a stable molecule that structurally resembles the transition state. This causes an antibody to be generated that recognizes and binds to the transition state, thereby stabilizing it. For example, the following transition state analog has been used to generate a catalytic antibody that catalyzes the hydrolysis of the structurally similar ester:

Chapter 16, Problem 94P, Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the , example 1

a. Draw a possible transition state for the hydrolysis reaction.

b. The following transition state analog is used to generate a catalytic antibody for the catalysis of ester hydrolysis. Draw the structure of an ester whose rate of hydrolysis would he increased by this catalytic antibody.

Chapter 16, Problem 94P, Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the , example 2

c. Design a transition state analog that catalyzes amide hydrolysis at the amide group indicated.

Chapter 16, Problem 94P, Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the , example 3

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Chapter 16, Problem 93P

Chapter 16, Problem 95P

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Chapter 16 Solutions

Organic Chemistry

Ch. 16.1 - The aromas of many flowers and fruits are due to...Ch. 16.1 - Prob. 2P Ch. 16.1 - Name the following:Ch. 16.1 - Prob. 4P Ch. 16.2 - Prob. 5P Ch. 16.2 - Which is longer, the carbon-oxygen single bond in...Ch. 16.2 - There are three carbon-oxygen bonds in methyl...Ch. 16.2 - Prob. 8P Ch. 16.4 - Prob. 9P Ch. 16.4 - Prob. 10P

Ch. 16.5 - a. What is the product of the reaction of acetyl...Ch. 16.6 - a. Which compound has the stretching vibration for...Ch. 16.6 - Using the pKa values listed in Table 15.1, predict...Ch. 16.6 - Is the following statement true or false? If the...Ch. 16.7 - What is the product of an acyl substitution...Ch. 16.8 - PROBLEM 16 Starting with acetyl chloride, what...Ch. 16.8 - Prob. 18P Ch. 16.9 - We saw that it is necessary to use excess amine in...Ch. 16.9 - Prob. 20P Ch. 16.9 - a. state three factors that cause the uncatalyzed...Ch. 16.10 - Prob. 23P Ch. 16.10 - Using the mechanism for the acid-catalyzed...Ch. 16.10 - Prob. 25P Ch. 16.10 - Prob. 27P Ch. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.11 - Prob. 30P Ch. 16.12 - Prob. 31P Ch. 16.12 - Prob. 32P Ch. 16.13 - Prob. 34P Ch. 16.13 - Which has a higher melting point, glyceryl...Ch. 16.13 - Draw the structure of an optically inactive fat...Ch. 16.13 - Draw the structure of an optically active fat...Ch. 16.14 - Show how each of the following esters could he...Ch. 16.14 - Prob. 39P Ch. 16.15 - Prob. 40P Ch. 16.15 - Which of the following reactions leads to the...Ch. 16.16 - Prob. 42P Ch. 16.16 - Prob. 43P Ch. 16.18 - Prob. 44P Ch. 16.18 - Prob. 45P Ch. 16.19 - Prob. 46P Ch. 16.19 - Which alkyl halides from the carboxylic acids...Ch. 16.20 - Prob. 49P Ch. 16.20 - Prob. 50P Ch. 16.20 - Prob. 51P Ch. 16.21 - Prob. 52P Ch. 16.21 - Prob. 53P Ch. 16.22 - How could you synthesize the following compounds...Ch. 16 - Prob. 55P Ch. 16 - Name the following:Ch. 16 - Prob. 57P Ch. 16 - What compound are obtained from the fallowing...Ch. 16 - a. Rank the following esters in order of...Ch. 16 - Because bromocyclohexane is a secondary alkyl...Ch. 16 - a. Which compound would you expect to have a...Ch. 16 - How could you use 1H NMR spectroscopy to...Ch. 16 - Prob. 63P Ch. 16 - a. When a carboxylic acid is dissolved in...Ch. 16 - Rank the following compounds in order of...Ch. 16 - Prob. 66P Ch. 16 - Prob. 67P Ch. 16 - Prob. 68P Ch. 16 - A compound with molecular formula C5H10O2 gives...Ch. 16 - Prob. 70P Ch. 16 - Prob. 71P Ch. 16 - Prob. 72P Ch. 16 - Two products, A and B, are obtained from the...Ch. 16 - Prob. 74P Ch. 16 - Prob. 75P Ch. 16 - Prob. 76P Ch. 16 - Prob. 77P Ch. 16 - When treated with an equivalent of methanol,...Ch. 16 - a. Identify the two products obtained from the...Ch. 16 - Prob. 80P Ch. 16 - Identity the major and minor products of the...Ch. 16 - Prob. 82P Ch. 16 - When a compound with molecular formula C11H14O2...Ch. 16 - Prob. 84P Ch. 16 - Prob. 85P Ch. 16 - The 1H NMR spectra for two esters with molecular...Ch. 16 - Show how the following compounds could be prepared...Ch. 16 - Prob. 88P Ch. 16 - Prob. 89P Ch. 16 - Prob. 90P Ch. 16 - The intermediate shown here is formed during the...Ch. 16 - Prob. 92P Ch. 16 - Propose a mechanism that accounts for the...Ch. 16 - Catalytic antibodies catalyze a reaction by...Ch. 16 - Prob. 95P

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Solution Summary: The author explains the structure of ester formed by catalytic antibody which increases rate of hydrolysis.

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Chapter 16 Solutions