Ketones react with sodium acetylide (the sodium salt of acetylene, Na*-:C=CH) to give alcohols. For example, the reaction of sodium acetylide with 2-butanone yields 3-methyl-1-pentyn-3-ol: H3C OH 1. Na+-:C=CH H3C CH2CH3 2. H30+ CH2CH3 HC=C 2-Butanone 3-Methyl-1-pentyn-3-ol (a) Is the product chiral? (b) Assuming that the reaction takes place with equal likelihood from both Re and Si faces of the carbonyl group, is the product optically active? Explain.
Ketones react with sodium acetylide (the sodium salt of acetylene, Na*-:C=CH) to give alcohols. For example, the reaction of sodium acetylide with 2-butanone yields 3-methyl-1-pentyn-3-ol: H3C OH 1. Na+-:C=CH H3C CH2CH3 2. H30+ CH2CH3 HC=C 2-Butanone 3-Methyl-1-pentyn-3-ol (a) Is the product chiral? (b) Assuming that the reaction takes place with equal likelihood from both Re and Si faces of the carbonyl group, is the product optically active? Explain.
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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