Organic Chemistry , 5 th Edition L. G. Wade, Jr. Chapter 17 Reactions of Aromatic Compounds. Jo Blackburn Richland College, Dallas, TX Dallas County Community College District ã 2003, Prentice Hall. =>. Electrophilic Aromatic Substitution.
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Organic Chemistry, 5th EditionL. G. Wade, Jr.
Chapter 17Reactions of Aromatic Compounds
Jo Blackburn
Richland College, Dallas, TX
Dallas County Community College District
ã 2003,Prentice Hall
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Electrophile substitutes for a hydrogen on the benzene ring.
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Use sulfuric acid with nitric acid to form the nitronium ion electrophile.
NO2+ then forms a
sigma complex with
benzene, loses H+ to
form nitrobenzene. =>
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Sulfur trioxide, SO3, in fuming sulfuric acid is the electrophile.
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Benzened6
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Intermediate is more stable if nitration occurs at the orthoor para position.
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Ortho attack
Meta attack
Para attack
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Aniline reacts with bromine water (without a catalyst) to yield the tribromide. Sodium bicarbonate is added to neutralize the HBr that’s also formed.
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Ortho and para attacks produce a bromonium ionand other resonance structures.
No bromonium ion possible with meta attack.
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The most strongly activating substituent will determine the position of the next substitution. May have mixtures.
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Acylbenzenes can be converted to alkylbenzenes by treatment with aqueous HCl and amalgamated zinc.
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Alkylbenzenes are oxidized to benzoic acid by hot KMnO4 or Na2Cr2O7/H2SO4.
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