9. By employing our understanding of nucleophiles and electrophiles, as well as kinetics and thermodynamics, we should be able to predict the electron-pushing arrow mechanisms, and the corresponding products, for reactions that we have not explicitly discussed in class. An example of this is the two-step addition of a hydrohalic acid (HX) across a pi bond, wherein the pi bond behaves as a the electron donor. However, as shown in the example below, there often exists the possibility of obtaining more than one product: H-Br Br A Br Br a. Using the pi bond between carbons 1 & 2 as the donor electrons, draw complete electron-pushing arrow mechanisms that account for the formation of each product (a-c) above. It is advisable for you to count your atoms in both the stating material and products. b. The formation of which product(s) above is kinetically favored? How do you know? c. The formation of which product(s) above is thermodynamically favored? How do you know? d. Sketch a Gibbs Free Energy Diagram that reflects your answers from parts (b) & (c).

9. By employing our understanding of nucleophiles and electrophiles, as well as kinetics and thermodynamics, we should be able to predict the electron-pushing arrow mechanisms, and the corresponding products, for reactions that we have not explicitly discussed in class. An example of this is the two-step addition of a hydrohalic acid (HX) across a pi bond, wherein the pi bond behaves as a the electron donor. However, as shown in the example below, there often exists the possibility of obtaining more than one product: H-Br Br A Br Br a. Using the pi bond between carbons 1 & 2 as the donor electrons, draw complete electron-pushing arrow mechanisms that account for the formation of each product (a-c) above. It is advisable for you to count your atoms in both the stating material and products. b. The formation of which product(s) above is kinetically favored? How do you know? c. The formation of which product(s) above is thermodynamically favored? How do you know? d. Sketch a Gibbs Free Energy Diagram that reflects your answers from parts (b) & (c).

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

Chapter8: Haloalkanes, Halogenation, And Radical Reactions

Section: Chapter Questions

Problem 8.34P

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