CAREY: ORGANIC CHEMISTRY
CAREY: ORGANIC CHEMISTRY
10th Edition
ISBN: 9781260364002
Author: VALUE EDITION
Publisher: MCG CUSTOM
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Chapter 18.12, Problem 20P
Interpretation Introduction

Interpretation:

The equations that outline two different syntheses of 3-methyl-3-heptene from 1-butanol and 2-butanol are to be discussed.

Concept introduction:

The reaction of an aldehyde or a ketone with triphenyl phosphonium ylide results in the formation of an alkene as the final product. This reaction is commonly known as Wittig reaction.

In the first step of the reaction, the nucleophilic attack of the ylide on the carbonyl carbon takes place to form betaine.

In the second step, the formation of the four-membered ring, oxaphosphetane occurs and in the final step, the alkene is formed as a product.

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AG/F-2° V 3. Before proceeding with this problem you may want to glance at p. 466 of your textbook where various oxo-phosphorus derivatives and their oxidation states are summarized. Shown below are Latimer diagrams for phosphorus at pH values at 0 and 14: -0.93 +0.38 -0.50 -0.51 -0.06 H3PO4 →H4P206 →H3PO3 →→H3PO₂ → P → PH3 Acidic solution Basic solution -0.28 -0.50 3--1.12 -1.57 -2.05 -0.89 PO HPO H₂PO₂ →P → PH3 -1.73 a) Under acidic conditions, H3PO4 can be reduced into H3PO3 directly (-0.28V), or via the formation and reduction of H4P206 (-0.93/+0.38V). Calculate the values of AG's for both processes; comment. (3 points) 0.5 PH P 0.0 -0.5 -1.0- -1.5- -2.0 H.PO, -2.3+ -3 -2 -1 1 2 3 2 H,PO, b) Frost diagram for phosphorus under acidic conditions is shown. Identify possible disproportionation and comproportionation processes; write out chemical equations describing them. (2 points) H,PO 4 S Oxidation stale, N
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2. Calculate the overall formation constant for [Fe(CN)6]³, given that the overall formation constant for [Fe(CN)6] 4 is ~1032, and that: Fe3+ (aq) + e = Fe²+ (aq) E° = +0.77 V [Fe(CN)6]³ (aq) + e¯ = [Fe(CN)6] (aq) E° = +0.36 V (4 points)

Chapter 18 Solutions

CAREY: ORGANIC CHEMISTRY

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