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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter9: Alkynes: An Introduction To Organic Synthesis

Section9.SE: Something Extra

Problem 21MP

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