EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Chapter 22, Problem 22.27P
Interpretation Introduction

(a)

Interpretation:

In the given reaction, the aromatic ring has just one chemically distinct, aromatic H, so a single electrophilic aromatic substitution will lead to a just a single product. The missing reagent to carry out the transformation is to be determined.

Concept introduction:

In Friedel Craft’s acylation reaction, the aromatic species is treated with acyl chloride. The product of Friedel Craft’s acylation reaction is ketone. In electrophilic aromatic substitution reactions, electrophiles typically must be generated in situ from more stable precursors that can be added as starting materials. Aluminum chloride acts as Lewis acid and forms a complex with chlorine. After heterolysis, electrophilic aromatic substitution reaction takes place. The arenium ion intermediate is a carbocation intermediate consisting of five sp2 hybridized C atoms and one sp3 hybridized C atom.

Interpretation Introduction

(b)

Interpretation:

In the given reaction, the aromatic ring has just one chemically distinct, aromatic H, so a single electrophilic aromatic substitution will lead to a just a single product. The product of the given reaction is to be determined.

Concept introduction:

Electrophiles in electrophilic aromatic substitution reactions typically must be generated in situ from more stable precursors that can be added as starting materials. The aluminum chloride acts as Lewis acid and forms a complex with chlorine. After heterolysis, electrophilic aromatic substitution reaction takes place. The arenium ion intermediate is a carbocation intermediate consisting of five sp2 hybridized C atoms and one sp3 hybridized C atom.

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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

Chapter 22 Solutions

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

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