When toluene is sulfonated (concentrated H₂SO4) at room temperature, predominantly (about 95% of the total) ortho and para substitution occurs. If elevated temperatures (150-200°C) and longer reaction times are employed, meta (chiefly) and para substitution account for some 95% of the products. Account for these differences in terms of kinetic and thermodynamic pathways. At the lower temperature, the reaction is observed. At higher temperatures, the reaction is be reached, the most stable isomer, controlled, and the usual o/p directive effects of the -CH3 group are controlled. At reaction times long enough for equilibrium to , is the principal product.

When toluene is sulfonated (concentrated H₂SO4) at room temperature, predominantly (about 95% of the total) ortho and para substitution occurs. If elevated temperatures (150-200°C) and longer reaction times are employed, meta (chiefly) and para substitution account for some 95% of the products. Account for these differences in terms of kinetic and thermodynamic pathways. At the lower temperature, the reaction is observed. At higher temperatures, the reaction is be reached, the most stable isomer, controlled, and the usual o/p directive effects of the -CH3 group are controlled. At reaction times long enough for equilibrium to , is the principal product.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.43P

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