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Lecture 31 - Periodate Cleavage, Retrosynthesis, and Green Chemistry

Lecture 31 - Periodate Cleavage, Retrosynthesis, and Green Chemistry

This video was recorded at CHEM 125b: Freshman Organic Chemistry II. The ability of periodic acid (HIO4) to cleave the C-C bond of vicinal diols and α-hydroxycarbonyl compounds allowed structure determination of sugars and their ketals before spectroscopy was available. Reduction of carbonyl compounds by organometallic or hydride reagents provides a range of schemes for synthesizing various alcohols, where preference may be dictated by the desire to avoid competing processes. Wittig olefination allows conversion of C=O to C=C with good control over constitutional isomerism. Pharmaceutical manufacturers have taken great interest in developing new solvents and reagents that minimize hazards, waste, and environmental impact of traditional reactions.

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