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Organic chemistry

Unit 1
carbon bonds
Introduction to Carbon BondsTypes of Carbon BondsDrawing Lewis Structures
Unit 2 • Chapter 3

Synthesis of Alcohols

Video Summary

Alcohols, containing the hydroxyl (-OH) group, are synthesized through various methods depending on the desired alcohol structure. Hydration of alkenes, adding water across the double bond, is a common approach, often catalyzed by acids. Hydroboration-oxidation provides anti-Markovnikov addition, placing the hydroxyl group on the less substituted carbon. Grignard reagents, organomagnesium halides, react with carbonyl compounds (aldehydes and ketones) to form alcohols after an acid workup. The carbonyl carbon becomes the new chiral center if the starting carbonyl is not symmetrical, allowing for the synthesis of chiral alcohols. Reduction of carbonyl compounds using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) is another important method. These reagents deliver a hydride ion (H-) to the carbonyl carbon, converting it to an alcohol. Each method offers unique regio- and stereochemical control, allowing for the synthesis of a wide array of alcohols.

Knowledge Check

Which of the following methods will yield an anti-Markovnikov alcohol?

What reagent is commonly used to reduce ketones to secondary alcohols?

Grignard reagents react with which functional group to produce alcohols?