The reaction between isocyanide 1 and ketone 2 occurs only after a base (t-BuOK) is added to a solution of the reactants in ethanol and CH2Cl2. The final product is nitrile 4, which is believed to arise from ethanolysis of intermediate 3 under the reaction conditions. Draw a plausible reaction mechanism to describe the formation of 4 from 1 and 2. Draw all intermediates and show all electron-pushing. You are not expected to know if your proposed mechanism is the actual mechanism supported by experimental evidence, but it must be reasonable, and the electron pushing should be correct. Hint: start by deprotonating 1 and forming the first bond, then label and map the atoms onto the intermediate. Ts N=C= t-BuO K NEC H NE EtOH, CH2Cl2 3 2

The reaction between isocyanide 1 and ketone 2 occurs only after a base (t-BuOK) is added to a solution of the reactants in ethanol and CH2Cl2. The final product is nitrile 4, which is believed to arise from ethanolysis of intermediate 3 under the reaction conditions. Draw a plausible reaction mechanism to describe the formation of 4 from 1 and 2. Draw all intermediates and show all electron-pushing. You are not expected to know if your proposed mechanism is the actual mechanism supported by experimental evidence, but it must be reasonable, and the electron pushing should be correct. Hint: start by deprotonating 1 and forming the first bond, then label and map the atoms onto the intermediate. Ts N=C= t-BuO K NEC H NE EtOH, CH2Cl2 3 2

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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