There are two isomeric cyclohexa-1,4-diene products when toluene undergoes the Birch reduction (see Problem 25.24). (a) Draw the mechanism that leads to the formation of the major product. (b) Will the Birchreduction of toluene occur faster or slower than the Birch reduction of benzene itself? Hint: Is –CH3 an electron-donating or an electron-withdrawing group? CH3Li(s), ROH?NH3(() PROBLEM 25.24 The Birch reduction of a monosubstitutedSubSubSubbenzene can produce two isomeric products, as shown. Whichone is the major product depends on whether the substituent iselectron donating or electron withdrawing (see Problems 25.60and 25.61 at the end of the chapter). Draw the mechanism thatleads to each product.Li(s), ROHNH3(4)

Birch reduction is the reduction reaction in which one of the double bond of the benzene or its…

Answered: CH3 Li(s), ROH ? NH3(() PROBLEM 25.24…

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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There are two isomeric cyclohexa-1,4-diene products when toluene undergoes the Birch reduction (see Problem 25.24). (a) Draw the mechanism that leads to the formation of the major product. (b) Will the Birch
reduction of toluene occur faster or slower than the Birch reduction of benzene itself? Hint: Is –CH₃ an electron-donating or an electron-withdrawing group?

PROBLEM 25.24 The Birch reduction of a monosubstituted
Sub
Sub
Sub
benzene can produce two isomeric products, as shown. Which
one is the major product depends on whether the substituent is
electron donating or electron withdrawing (see Problems 25.60
and 25.61 at the end of the chapter). Draw the mechanism that
leads to each product.
Li(s), ROH
NH3(4)

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