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Chapter 22-2 - CHEM 262 Wei You Chapter 22 Reaction of...

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6/13/10 11 CHEM 262 Wei You Chapter 22. Reaction of Benzene and its Derivatives (2)
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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
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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
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6/13/10 Di- and 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 CH O O CR COH SO 3 H COR O CNH
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