From each pair of compounds, choose the one with the indicated property and explain your choice. a) is racemized when placed in basic solution: (R)-4-methyl-2-hexanone or (R)-3-methyl-2-hexanone b) forms an enamine when treated with a ketone: diethylmethylamine or diethylamine

From each pair of compounds, choose the one with the indicated property and explain your choice. a) is racemized when placed in basic solution: (R)-4-methyl-2-hexanone or (R)-3-methyl-2-hexanone b) forms an enamine when treated with a ketone: diethylmethylamine or diethylamine

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter26: Aldol And Claisen Reactions

Section: Chapter Questions

Problem 20E

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

From each pair of compounds, choose the one with the indicated
property and explain your choice.
a) is racemized when placed in basic solution: (R)-4-methyl-2-hexanone or
(R)-3-methyl-2-hexanone
b)
forms an enamine when treated with a ketone: diethylmethylamine or
diethylamine

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