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.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.38P: A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted...
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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:
5-76
H3C OH
1. Nat-:C=CH
H3C
CH2CH3
2. Hзо+
CH2CH3
HC
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.
Transcribed Image Text: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: 5-76 H3C OH 1. Nat-:C=CH H3C CH2CH3 2. Hзо+ CH2CH3 HC 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.
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