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Chemistry: The Central Science | 14th Edition | ISBN: 9780134414232 | Authors: Theodore E. Brown; H. Eugene LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward; Matthew E. Stoltzfus ISBN: 9780134414232 1274

Solution for problem 20.6 Chapter 20

Chemistry: The Central Science | 14th Edition

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Chemistry: The Central Science | 14th Edition | ISBN: 9780134414232 | Authors: Theodore E. Brown; H. Eugene LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward; Matthew E. Stoltzfus

Chemistry: The Central Science | 14th Edition

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Problem 20.6

Consider the following table of standard electrode potentials for a series of hypothetical reactions in aqueous solution:

(a) Which substance is the strongest oxidizing agent? Which is weakest?

(b) Which substance is the strongest reducing agent? Which is weakest?

(c) Which substance(s) can oxidize \(\mathrm{C}^{2+}\)? [Sections 20.4 and 20.5]

Text Transcription:

{C}^{2+}

Step-by-Step Solution:
Step 1 of 3

Chapter 23 and 24 General Ketone with Base reaction Malonic ester synthesis ● Decarboxylation = loss of CO2 ● Carboxylic acid with 1 or 2 carbon chains attached to the α carbon Acetoacetic ester synthesis ● Methyl ketone with 1 or 2 R groups attached to the other α carbon Mechanism Acetoacetic ester synthesis How to Make Chapter 24 ● Enolate reacts with carbonyl compound Aldol Reaction ● 2 aldehydes or ketones react product is a β- hydroxy carbonyl Mechanism of aldol ● 2 Aldehydes = Aldol products favored ● 2 Ketones = Aldol starting materials favored ● β – hydroxyl carbonyl compounds can undergo base-catalyzed dehydration ● All alcohols undergo acid- catalyzed dehydration Mechanism ● This is likely to happen with conjugated molecules Aldol reaction ● Enolate (nucleophile) + aldehyde or ketone in base ● Product is β- hydroxyl carbonyl Crossed Aldol reaction ● Two different carbonyl compounds reacting ● ● Better results if only one compound has α-H’s or it's much more acidic ● Better if one is much more electrophilic Directed Aldol ● Selectively deprotonate 1​ compound at low temperature with LDA ● Then add second compound 1:1 of Ketone: LDA ~100% of enolate formed Dicarbonyl compounds can do intramolecular aldol

Step 2 of 3

Chapter 20, Problem 20.6 is Solved
Step 3 of 3

Textbook: Chemistry: The Central Science
Edition: 14
Author: Theodore E. Brown; H. Eugene LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward; Matthew E. Stoltzfus
ISBN: 9780134414232

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