The specific angle of rotation of (R)-2-bromobutane is -23.1°. Treatment of (R)-2-bromobutane with potassium bromide produces a racemic mixture of (R)- and (S)-2-bromobutane, which is optically inactive. The rate at which the product's angle of rotation decreases is directly proportional to the concentration of KBr. Does this suggest that the reaction takes place by an SN1 or an SŅ2 mechanism? Explain.

The specific angle of rotation of (R)-2-bromobutane is -23.1°. Treatment of (R)-2-bromobutane with potassium bromide produces a racemic mixture of (R)- and (S)-2-bromobutane, which is optically inactive. The rate at which the product's angle of rotation decreases is directly proportional to the concentration of KBr. Does this suggest that the reaction takes place by an SN1 or an SŅ2 mechanism? 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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.50P

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