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 tothe formation of the major product.(b) Will the Birchreduction of benzoic acid occur faster or slower than theBirch reduction of benzene itself?Hint: Is –CO2H anelectron-donating or an electron-withdrawing group? CO,HLi(s), ROHNH3(4) 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- Reduction of aromatic rings by reaction with Na / K / Li in liquid ammonia in…

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: The Molecular Science

5th Edition

ISBN:9781285199047

Author:John W. Moore, Conrad L. Stanitski

Publisher:John W. Moore, Conrad L. Stanitski

Chapter20: Chemistry Of Selected Transition Elements And Coordination Compounds

Section: Chapter Questions

Problem 84QRT

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