1. Acetaldehyde (2 carbon aldehyde) is being reacted with hydroxide in ethanol. The hydrogen alpha to the carbonyl is abstracted by the electron pair on the oxygen of the hydroxide giving water. The product enolate has electron pair at the alpha carbon. The enolate can tautomerize which is described next. The electron pair on the alpha carbon can move toward the carbon attached to the oxygen resulting in a new pi-bond being formed. At the same time the pi-bond between the carbon and oxygen breaks with an electron pair flowing to the oxygen. The enolate with the electron pair at the alpha carbon can react with another molecule of acetaldehyde. The electron pair on the alpha carbon can form a sigma-bond with the carbon of the carbonyl simultaneously breaking the pi-bond between the carbonyl carbon and oxygen. The electron pair from the pi-bond moves to the oxygen giving it a negative charge. The electron pair on the oxygen abstracts a hydrogen from the water regenerating hydroxide. The product is an aldol product with the alcohol beta relative to the aldehyde.
1. Acetaldehyde (2 carbon aldehyde) is being reacted with hydroxide in ethanol. The hydrogen alpha to the carbonyl is abstracted by the electron pair on the oxygen of the hydroxide giving water. The product enolate has electron pair at the alpha carbon. The enolate can tautomerize which is described next. The electron pair on the alpha carbon can move toward the carbon attached to the oxygen resulting in a new pi-bond being formed. At the same time the pi-bond between the carbon and oxygen breaks with an electron pair flowing to the oxygen. The enolate with the electron pair at the alpha carbon can react with another molecule of acetaldehyde. The electron pair on the alpha carbon can form a sigma-bond with the carbon of the carbonyl simultaneously breaking the pi-bond between the carbonyl carbon and oxygen. The electron pair from the pi-bond moves to the oxygen giving it a negative charge. The electron pair on the oxygen abstracts a hydrogen from the water regenerating hydroxide. The product is an aldol product with the alcohol beta relative to the aldehyde.
Chapter3: Mechanisms
Section: Chapter Questions
Problem 29EQ
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Draw the reaction
Transcribed Image Text:1. Acetaldehyde (2 carbon aldehyde) is being reacted with hydroxide in ethanol. The hydrogen
alpha to the carbonyl is abstracted by the electron pair on the oxygen of the hydroxide giving
water. The product enolate has electron pair at the alpha carbon. The enolate can tautomerize
which is described next. The electron pair on the alpha carbon can move toward the carbon
attached to the oxygen resulting in a new pi-bond being formed. At the same time the pi-bond
between the carbon and oxygen breaks with an electron pair flowing to the oxygen.
The enolate with the electron pair at the alpha carbon can react with another molecule of
acetaldehyde. The electron pair on the alpha carbon can form a sigma-bond with the carbon of
the carbonyl simultaneously breaking the pi-bond between the carbonyl carbon and oxygen.
The electron pair from the pi-bond moves to the oxygen giving it a negative charge. The
electron pair on the oxygen abstracts a hydrogen from the water regenerating hydroxide. The
product is an aldol product with the alcohol beta relative to the aldehyde.
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