Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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12. When (S)-1-bromo-1-fluoroethane reacts with sodium methoxide, an SN2 reaction takes place in which the atom is replaced by a methoxy group (OMe). The product of this reaction is (S)-1-fluoro-1-methoxyethane. How can it be that the starting material and the product both have the S configuration? Shouldn't SN2 involve the change in configuration? Draw the starting material and the product of inversion, and then explain the anomaly.
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Transcribed Image Text:12. When (S)-1-bromo-1-fluoroethane reacts with sodium methoxide, an SN2 reaction takes place in which the atom is replaced by a methoxy group (OMe). The product of this reaction is (S)-1-fluoro-1-methoxyethane. How can it be that the starting material and the product both have the S configuration? Shouldn't SN2 involve the change in configuration? Draw the starting material and the product of inversion, and then explain the anomaly.
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