4. When buta-1,3-diene reacts with HBr, two different products form: 3-bromobut-1-ene (A) and 1-bromobut-2-ene (B). At low temperature (0 °C), product A is much more prevalent in the product mixture, even though it is the less thermodynamically favored of the two products. At higher temperature (80 °C), product B predominates instead. a. (i) Write a complete mechanism that explains how the formation of two different products from one starting material is possible. (ii) Show all arrows, charges, and lone electrons. b. (i) Draw a complete reaction coordinate diagram (RCD) corresponding to the reaction described above. (ii) Label the axes, all transition states, and all activation energies for both the forward and reverse reactions. (iii) Draw a structure for each reactant, product, intermediate, or transition state on your RCD. c. (i) Explain why product B is energetically favored. Then, using an appropriate molecular energy distribution diagram, (ii) explain why the less favored product (A) forms at low temperature instead.

4. When buta-1,3-diene reacts with HBr, two different products form: 3-bromobut-1-ene (A) and 1-bromobut-2-ene (B). At low temperature (0 °C), product A is much more prevalent in the product mixture, even though it is the less thermodynamically favored of the two products. At higher temperature (80 °C), product B predominates instead. a. (i) Write a complete mechanism that explains how the formation of two different products from one starting material is possible. (ii) Show all arrows, charges, and lone electrons. b. (i) Draw a complete reaction coordinate diagram (RCD) corresponding to the reaction described above. (ii) Label the axes, all transition states, and all activation energies for both the forward and reverse reactions. (iii) Draw a structure for each reactant, product, intermediate, or transition state on your RCD. c. (i) Explain why product B is energetically favored. Then, using an appropriate molecular energy distribution diagram, (ii) explain why the less favored product (A) forms at low temperature instead.

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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4. When buta-1,3-diene reacts with HBr, two different products form: 3-bromobut-1-ene (A) and 1-bromobut-2-ene (B). At
low temperature (0 °C), product A is much more prevalent in the product mixture, even though it is the less
thermodynamically favored of the two products. At higher temperature (80 °C), product B predominates instead.
a. (i) Write a complete mechanism that explains how the formation of two different products from one starting
material is possible. (ii) Show all arrows, charges, and lone electrons.
b. (i) Draw a complete reaction coordinate diagram (RCD) corresponding to the reaction described above. (ii) Label
the axes, all transition states, and all activation energies for both the forward and reverse reactions. (iii) Draw a
structure for each reactant, product, intermediate, or transition state on your RCD.
c. (i) Explain why product B is energetically favored. Then, using an appropriate molecular energy distribution
diagram, (ii) explain why the less favored product (A) forms at low temperature instead.
d. When the
pove reaction occurs at higher temperature, the more thermodynamically favorable compound (B) is
formed in higher proportion. Using your RCD diagram from above, explain this behavior.

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