310-31 - CH 310 N LECTURE 31 Textbook Assignment: Chap 22...

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1 CH 310 N LECTURE 31 Textbook Assignment: Chap 22 Rxns of Benzene & Derivatives Homework (for credit): POW 10 posted (Due Apr 11) Today’s Topics: EAS intro; rxn energetics; mechanisms Notice & Announcements: 2 Reactions of Reactions of Benzene & Benzene & Its Derivatives Its Derivatives Chapter 21
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3 Reactions of Benzene Reactions of Benzene The most characteristic reaction of aromatic compounds is substitution at a ring carbon: + + Chlorobenzene Halogenation: H Cl 2 FeCl 3 HCl + + Nitrobenzene Nitration: HN O 2 HNO 3 H 2 SO 4 H 2 O 4 + Benzenesulfonic acid Sulfonation: HS O 3 H SO 3 H 2 4 + + An alkylbenzene Alkylation: R RX AlX 3 HX + + Acylation: An acylbenzene H RCX 3 O CR O H Reactions of Benzene Reactions of Benzene
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R Arenes Alkylbenzenes AlCl 3 RC l Carbon-Carbon Bond Formations: 6 Electrophilic Electrophilic Aromatic Substitution Aromatic Substitution • Electrophilic Electrophilic aromatic substitution: aromatic substitution: a reaction in which a hydrogen atom of an aromatic ring is replaced by an electrophile • In this section: – several common types of electrophiles – how each is generated – the mechanism by which each replaces hydrogen + + H E E + H +
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7 EAS: General Mechanism EAS: General Mechanism • A general mechanism
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310-31 - CH 310 N LECTURE 31 Textbook Assignment: Chap 22...

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