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ChemistryOrganic ChemistryThe reaction of an α -diketone with concentrated sodium or potassium hydroxide to give the salt of an α-hydroxyacid is given the general name benzil-benzilic acid rearrangement. It is illustrated by the conversion of benzil to sodium benzilate and then to benzilic acid. Propose a mechanism for this rearrangement.The reaction of an α -diketone with concentrated sodium or potassium hydroxide to give the salt of an α-hydroxyacid is given the general name benzil-benzilic acid rearrangement. It is illustrated by the conversion of benzil to sodium benzilate and then to benzilic acid. Propose a mechanism for this rearrangement.
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Organic Chemistry
8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
BuyFindlaunch
Organic Chemistry
8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Solutions
Chapter
Section
Chapter 17, Problem 17.24P
Textbook Problem
The reaction of an α-diketone with concentrated sodium or potassium hydroxide to give the salt of an α-hydroxyacid is given the general name benzil-benzilic acid rearrangement. It is illustrated by the conversion of benzil to sodium benzilate and then to benzilic acid. Propose a mechanism for this rearrangement.
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Organic Chemistry
Ch. 17.2 - Each of these carboxylic acids has a...Ch. 17.4 - Which is the stronger acid in each pair?Ch. 17.4 - Write equations for the reaction of each acid in...Ch. 17.7 - Complete the equation for each Fischer...Ch. 17.8 - Complete the equation for each reaction.Ch. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.9 - Account for the observation that the following...
Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Draw a structural formula for each compound. (a)...Ch. 17 - Megatomoic acid, the sex attractant of the female...Ch. 17 - Draw a structural formula for each salt. (a)...Ch. 17 - The monopotassium salt of oxalic acid is present...Ch. 17 - Potassium sorbate is added as a preservative to...Ch. 17 - Zinc 10-undecenoate, the zinc salt of...Ch. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Arrange the compounds in each set in the order of...Ch. 17 - Acetic acid has a boiling point of 118C, whereas...Ch. 17 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 17 - Complete each reaction.Ch. 17 - Show how to bring about each conversion in good...Ch. 17 - Show how to prepare pentanoic acid from each...Ch. 17 - Draw the structural formula of a compound with the...Ch. 17 - Show the reagents and experimental conditions...Ch. 17 - Succinic acid can be synthesized by the following...Ch. 17 - The reaction of an -diketone with concentrated...Ch. 17 - Select the stronger acid in each set. (a) Phenol...Ch. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - The normal pH range for blood plasma is 7.357.45....Ch. 17 - The Ka1 of ascorbic acid is 7.94 105. Would you...Ch. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Complete these examples of Fischer esterification....Ch. 17 - Benzocaine, a topical anesthetic, is prepared by...Ch. 17 - Name the carboxylic acid and alcohol from which...Ch. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - When heated, carboxylic salts in which there is a...Ch. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - In Section 17.7B, we suggested that the mechanism...Ch. 17 - We have studied Fischer esterification, in which a...Ch. 17 - Use the reaction roadmap you made for Problems...Ch. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Diazomethane, CH2N2, is used in the organic...Ch. 17 - Complete the following Fischer esterification...Ch. 17 - So far, you have seen a number of reducing agents...
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