310-32 - CH 310 N LECTURE 32 Textbook Assignment: Chap 22...

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1 CH 310 N LECTURE 32 Textbook Assignment: Chap 22 Rxns of Benzene & Derivatives Homework (for credit): POW 10 posted (Due Apr 11) Today’s Topics: EAS continued-Disubstitution; directing effects Notice & Announcements: “Plastic Surgery” William C. Pederson, MD - Hand Surgeon 2 EAS: General Mechanism EAS: General Mechanism • A general mechanism • Key question: What is the electrophile and how is it generated? + E + H E H + slow, rate determining Step 1: Step 2: E H + fast + H + E Electro - phile Resonance-stabilized cation intermediate
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3 2. F-C alkylation fails on benzene rings bearing one or more of these strongly electron- withdrawing groups Y RX AlCl 3 SO 3 HN O 2 NR 3 + CF 3 CCl 3 CN CH O CR O COH O COR O CNH 2 O + No reaction When Y Equals Any of These Groups, the Benzene Ring Does Not Undergo Friedel-Crafts Alkylation Friedel Friedel -Crafts Alkylation Crafts Alkylation 4
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5 The The “De De -activation activation ” of of Aromatic Systems Aromatic Systems Note: deactivation refers to the rate of EAS 6 • Friedel-Crafts acylation acylation forms a new C-C bond between a benzene ring and an acyl group: O Cl CH 3 CCl O AlCl 3 3 O O HCl + Benzene Acetophenone Acetyl chloride 4-Phenylbutanoyl α -Tetralone + + Friedel Friedel -Crafts Acylation Crafts Acylation
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This note was uploaded on 04/24/2011 for the course CH 56255 taught by Professor Colapret during the Spring '11 term at University of Texas at Austin.

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310-32 - CH 310 N LECTURE 32 Textbook Assignment: Chap 22...

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