Chapter 22-2

Chapter 22-2 - 6/13/10 11 CHEM 262 Wei You Chapter 22....

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Unformatted text preview: 6/13/10 11 CHEM 262 Wei You Chapter 22. Reaction of Benzene and its Derivatives (2) 6/13/10 Di- and Polysubstitution • Orientation: – substituents are classified as either ortho-para directing (direct incoming groups preferentially to ortho & para positions) or meta directing (direct to meta position) toward further substitution • Rate – substituents are classified as activating (cause the rate of a second substitution to be greater than that for benzene) or deactivating (cause rate to be lower) toward further substitution 22 6/13/10 Di- and Polysubstitution –-OCH3 is ortho-para directing –-NO2 is meta directing OCH 3 HNO 3 CH 3 COOH OCH 3 NO 2 OCH 3 NO 2 H 2 O p-Nitroanisole (55%) o-Nitroanisole (44%) Anisole + + + COOH HNO 3 H 2 SO 4 NO 2 COOH COOH NO 2 NO 2 COOH 100°C m- Nitro- benzoic acid (80%) Benzoic acid + + + o- Nitro- benzoic acid (18%) p- Nitro- benzoic acid (2%) 33 6/13/10 Di- and Polysubstitution Weakly activating Ortho-para Directing Weakly deactivating Moderately activating Strongly activating N H 2 N HR N R 2 OH N HCR N HCAr OR OCAr OCR R F Cl Br I : : : : : : : : : : : : : :: : : :: :: : : : : Strongly deactivating...
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This note was uploaded on 06/12/2010 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

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Chapter 22-2 - 6/13/10 11 CHEM 262 Wei You Chapter 22....

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