310-33 - CH 310 N LECTURE 33 Textbook Assignment: Chap 22...

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1 CH 310 N LECTURE 33 Textbook Assignment: Chap 22 Rxns of Benzene & Derivatives Homework (for credit): POW 11 posted (Due Apr 18) Today’s Topics: EAS continued-Disubstitution; directing effects Notice & Announcements: 2
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3 -OCH 3 is ortho-para directing: –- CO 2 H is meta directing OCH 3 HNO 3 CH 3 COOH 3 NO 2 3 2 H 2 O p -Nitroanisole (55%) o (44%) Anisole + + + 3 H 2 SO 4 2 2 2 100°C m- Nitro- benzoic acid (80%) Benzoic acid ++ + o- benzoic acid (18%) p- acid (2%) Di Di - and and Polysubstitution Polysubstitution 4 Di Di - and and Polysubstitution Polysubstitution Weakly activating Ortho-para Directing Weakly deactivating Moderately activating Strongly activating NH 2 NHR NR 2 OH NHCR NHCAr OR OCAr OCR R F Cl Br I : :: : : : : Strongly deactivating Moderately deactivating OO CR COH 3 H COR O CNH 2 2 3 + CF 3 CCl 3 Meta Directing CN O O O O
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5 the order of steps is important: CH 3 K 2 Cr 2 O 7 H 2 SO 4 HNO 3 H 2 4 3 NO 2 COOH H 2 SO 4 HNO 3 K 2 2 O 7 H 2 SO 4 2 2 m -Nitrobenzoic acid p -Nitrobenzoic Di Di - and and Polysubstitution Polysubstitution 6 Theory of Directing Effects Theory of Directing Effects • The rate of EAS is limited by the slowest step in the reaction • For almost every EAS, the rate- determining step is attack of E + on the aromatic ring to give a resonance- stabilized cation intermediate •The more stable this cation intermediate, the faster the rate- determining step
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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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310-33 - CH 310 N LECTURE 33 Textbook Assignment: Chap 22...

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