7th Edition

ISBN: 9780321803221

Author: Paula Y. Bruice

Publisher: Prentice Hall

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Textbook Question

Chapter 18, Problem 77P

A carboxylic arid is formed when an α-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for the following Favorskii reaction. (Hint: In the first step, HO^- removes a proton from the α-carbon that is not bonded to Br; a three-membered ring is formed in the second step; and HO^- is a nucleophile in the thud step.)

Chapter 18, Problem 77P, A carboxylic arid is formed when an -haloketone reacts with hydroxide ion. This reaction is called a

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Chapter 18, Problem 76P

Chapter 18, Problem 78P

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Chapter 18 Solutions

Organic Chemistry

Ch. 18.1 - Prob. 1P Ch. 18.1 - Prob. 2P Ch. 18.1 - Prob. 3P Ch. 18.1 - Prob. 4P Ch. 18.1 - PROBLEM 5♦ List the compounds in each of the...Ch. 18.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 18.3 - Draw the enol tautomers for each of the following...Ch. 18.3 - Prob. 8P Ch. 18.4 - Prob. 9P Ch. 18.4 - Prob. 10P

Ch. 18.5 - Show how the following compounds can be prepared...Ch. 18.6 - What compound is formed when a dilute solution of...Ch. 18.7 - Prob. 13P Ch. 18.7 - Prob. 14P Ch. 18.7 - How many stereoisomers are obtained from each of...Ch. 18.7 - Prob. 16P Ch. 18.8 - Prob. 17P Ch. 18.9 - Prob. 18P Ch. 18.9 - Prob. 19P Ch. 18.10 - Prob. 20P Ch. 18.10 - What aldehyde or ketone would be obtained when...Ch. 18.11 - Prob. 22P Ch. 18.12 - Prob. 24P Ch. 18.12 - What two carbonyl compound are required for the...Ch. 18.12 - Propose a mechanism for the following reaction:Ch. 18.13 - Draw the products of the following reactions:Ch. 18.13 - Prob. 28P Ch. 18.13 - Prob. 29P Ch. 18.14 - Prob. 30P Ch. 18.15 - Write the mechanism for the reaction of a...Ch. 18.15 - Prob. 32P Ch. 18.15 - Prob. 33P Ch. 18.15 - Draw the product of the reaction of each of the...Ch. 18.16 - Draw the product obtained by heating each pair of...Ch. 18.16 - Prob. 36P Ch. 18.17 - Prob. 37P Ch. 18.18 - Prob. 38P Ch. 18.18 - Prob. 39P Ch. 18.19 - Prob. 40P Ch. 18.20 - Prob. 42P Ch. 18.21 - Propose a mechanism for the formation of...Ch. 18.21 - Prob. 44P Ch. 18.21 - a. If the biosynthesis of palmitic acid were...Ch. 18.21 - Prob. 46P Ch. 18 - Prob. 47P Ch. 18 - Prob. 48P Ch. 18 - Number the following compounds in order of...Ch. 18 - The 1H NMR chemical shifts of nitromethane,...Ch. 18 - Prob. 51P Ch. 18 - Draw the products of the following reactions: a....Ch. 18 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 18 - Prob. 54P Ch. 18 - Prob. 55P Ch. 18 - Prob. 56P Ch. 18 - Prob. 57P Ch. 18 - Identify A-L. (Hint: A shows three singles in its...Ch. 18 - Using cyclopentanone as the reactant, show the...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 61P Ch. 18 - Prob. 62P Ch. 18 - Prob. 63P Ch. 18 - The ketone whose 1H NMR spectrum is shown here was...Ch. 18 - Prob. 65P Ch. 18 - Compound A with molecular formula C6H10 has two...Ch. 18 - Indicate how each of the following compounds can...Ch. 18 - Draw the products of the following reactions:Ch. 18 - Prob. 69P Ch. 18 - a. Show how the amino acid alanine can be...Ch. 18 - Prob. 71P Ch. 18 - Show how the following compounds can be...Ch. 18 - Explain why the following bromoketone forms...Ch. 18 - Prob. 74P Ch. 18 - What carbonyl compounds are required to prepare a...Ch. 18 - Prob. 76P Ch. 18 - A carboxylic arid is formed when an -haloketone...Ch. 18 - An , -unsaturated carbonyl compound can be...Ch. 18 - Prob. 79P Ch. 18 - A Cannizzaro reaction is the reaction of an...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - The following reaction is known as the benzoni...Ch. 18 - Prob. 83P Ch. 18 - Prob. 84P Ch. 18 - Prob. 85P Ch. 18 - Prob. 86P Ch. 18 - Propose a mechanism for the following reaction:

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Solution Summary: The author explains the mechanism for the reaction of a -haloketone with hydroxide ion.

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Chapter 18 Solutions