Explain each observation: (a) When (R)-2-methylcyclohexanone is treated with NaOH in H2O, the optically active solution gradually loses optical activity. (b) When (R)-3-methylcyclohexanone is treated with NaOH in H2O, the solution remains optically active.

Explain each observation: (a) When (R)-2-methylcyclohexanone is treated with NaOH in H2O, the optically active solution gradually loses optical activity. (b) When (R)-3-methylcyclohexanone is treated with NaOH in H2O, the solution remains optically active.

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.

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