(a) When toluene (methyl benzene) is sulfonated through reaction with concentrated H2SO4 at room temperature, predominantly (~ 95% of total) ortho- and para-substitution occurs. If elevated reaction temperatures (150 – 200°C) and longer reaction times are employed, meta- (chiefly) and para-substitution account for 95% of the products. Provide a rationale for this finding using words and reaction schemes.

(a) When toluene (methyl benzene) is sulfonated through reaction with concentrated H2SO4 at room temperature, predominantly (~ 95% of total) ortho- and para-substitution occurs. If elevated reaction temperatures (150 – 200°C) and longer reaction times are employed, meta- (chiefly) and para-substitution account for 95% of the products. Provide a rationale for this finding using words and reaction schemes.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.8: Oxidation Of Aromatic Compounds

Problem 20P

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