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Ch_322b_16.06 - Chapter 16.6 lecture note

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Alcohols, R-OH, add in a similar way as water to carbonyl compounds. One important difference is that, overall, two equivalents of ROH can react with aldehydes and ketones. Hemiacetals are formed from the addition of one equivalent of ROH . Additions of Alcohols: Hemiacetals and Acetals C :O: = R H + R'OH C HO R H OR' hemiacetal Acetals result from the addition of two equivalents of ROH . C :O: = R H + 2R'OH C R'O R H OR' acetal + H 2 O
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Typical Reaction Conditions for Acetal Formation The rate of the addition of alcohol is accelerated by acid and, like the hydration reaction, there is an equilibrium between the carbonyl compound and the tetrahedral product. To promote hemiacetal and acetal formation, the reaction is run by allowing the aldehyde to stand with a large excess of the alcohol with a small amount of anhydrous acid. The water produced can be removed as an azeotrope with benzene to drive the reaction to completion.
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