Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 15.SE, Problem 54AP

After the reaction below, the chemical shift of Ha moves downfield from 6.98 ppm to 7.30 ppm. Explain.

Chapter 15.SE, Problem 54AP, After the reaction below, the chemical shift of Ha moves downfield from 6.98 ppm to 7.30 ppm.

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The following mechanism is proposed: C6H5COOH ⇌ C6H5CO2H2+   (fast) C6H5CO2H2+ ⇌ C6H5CO+ + H2O   (fast) C6H5CO+ + HX + H2O ⟶ C6H6NH2 + N2 + CO2  (slow) The overall enthalpy change is -237.6 kJ. Sketch a reaction-energy diagram consistent with the above mechanism and the enthalpy change. Label the enthalpy change and each transition state. Explain the appearance of your graph.

Chapter 15 Solutions

Organic Chemistry

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