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CO,H Li(s), ROH NH3(4) 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)

CO,H Li(s), ROH NH3(4) 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)

Chemistry
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 benzoic acid 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 benzoic acid occur faster or slower than the
Birch reduction of benzene itself?

Hint: Is –CO2H an
electron-donating or an electron-withdrawing group?

CO,H Li(s), ROH NH3(4)
Transcribed Image Text:CO,H Li(s), ROH NH3(4)
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)
Transcribed Image Text: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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