Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 12, Problem 3PP
Interpretation Introduction

Interpretation:

Accomplishment of each of the given transformations is to be shown.

Concept introduction:

Swern Oxidation converts primary and secondary alcohols into aldehydes and ketones, respectively. The catalyst used is DMSO (dimethyl sulfoxide), oxalyl chloride in triethylamine (organic base).

Reduction of alkyl halides to hydrocarbons is achieved by treating alkyl halides with lithium aluminum hydride (LiAlH4).

Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to carboxylic acids is achieved by chromic acid and water. Secondary alcohols are oxidized into ketones and no further reaction is involved, since there are no hydrogens attached to the oxygen to be removed.

Pyridinium Chlorochromate (PPC): PPC is formed from pyridine, hydrochloric acid and chromium oxide. This allows for controlled oxidation since this reaction takes place in anhydrous conditions.

Potassium Permanganate: Potassium permanganate is a strong oxidizing agent. It converts the primary alcohols and aldehydes to their corresponding carboxylic acids. It converts secondary alcohols to ketones. This is not a controlled reaction since the reaction occurs in aqueous medium.

When an oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols, or to form carboxylic acids from aldehydes. Compounds with no hydrogen attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.

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