ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 16, Problem 30P
Interpretation Introduction

Interpretation:

An efficient synthesis of pheromone (4-methyl-3-heptanol) from alcohols of five carbon atoms or fewer is to be suggested.

Concept Introduction:

Alochol on oxidation yields a carbonyl compound. The resulting carbonyl compound is an aldehyde, ketone, or a carboxylic acid depending upon the type of alcohol that is been used.

A primary alcohol is oxidized to a carbonyl compound containing an aldehyde group.

A secondary alcohol is oxidized to a carbonyl compound containing a keto group.

Pyridinium chlorochromate (PCC) in dichloromethane, pyridinium dichromate (PDC) in dichloromethane are used in oxidizing primary and secondary alcohol to carbonyl compounds.

Phosphorous tribromide converts alcohols to alkyl bromides.

Aldehydes on reactions of Grignard reagents yield secondary alcohols.

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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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Chapter 16 Solutions

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