According to the rules for reasonable mechanisms, the E1 reaction shown here should undergo a 1,2-hydride shift. However, the same product is produced regardless of whether the rearrangement occurs. Br H20, heat (a) Draw the mechanism that includes that carbocation rearrangement. (b) Draw the mechanism that does not include the rearrangement. (c) Experimentally, how can we use 13C isotope labeling to determine whether the rearrangement occurs? In other words, can a 1ºc atom in the substrate be replaced by a 1°C atom so that the E1 products would depend on whether the rearrangement takes place? (d) How can we use deuterium isotope labeling to determine whether the rearrangement occurs?

According to the rules for reasonable mechanisms, the E1 reaction shown here should undergo a 1,2-hydride shift. However, the same product is produced regardless of whether the rearrangement occurs. Br H20, heat (a) Draw the mechanism that includes that carbocation rearrangement. (b) Draw the mechanism that does not include the rearrangement. (c) Experimentally, how can we use 13C isotope labeling to determine whether the rearrangement occurs? In other words, can a 1ºc atom in the substrate be replaced by a 1°C atom so that the E1 products would depend on whether the rearrangement takes place? (d) How can we use deuterium isotope labeling to determine whether the rearrangement occurs?

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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