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CH3 Li(s), ROH ? NH3(() 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)

CH3 Li(s), ROH ? NH3(() 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: The Molecular Science
Chemistry: The Molecular Science
5th Edition
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:John W. Moore, Conrad L. Stanitski
Chapter7: Molecular Structures
Section: Chapter Questions
Problem 31QRT
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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?

CH3 Li(s), ROH ? NH3(()
Transcribed Image Text:CH3 Li(s), ROH ? NH3(()
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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