Concept explainers
Interpretation:
The oxidizing or reducing agents that would be used to carry out each of the given transformation is to be determined.
Concept introduction:
Swern oxidation reaction converts primary and secondary alcohols into
Reduction of carbonyl compounds to hydrocarbons is achieved by treating carbonyl compounds with lithium aluminum hydride
Sodium borohydride
Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to
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: It is a strong oxidation agent that 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 oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols or form carboxylic acids from aldehydes. Compounds with no hydrogen atom attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning