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lecture 22.2 - Organic Chemistry William H Brown...

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22- 22-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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22- 22-2 Reactions of Reactions of Benzene and its Benzene and its Derivatives Derivatives Chapter 22 Chapter 22
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22- 22-3 Di- and Polysubstitution Di- and Polysubstitution Orientation on nitration of monosubstituted benzenes OCH 3 Cl Br COOH CN NO 2 ortho meta para ortho + para meta 44 - 55 99 trace 70 - 30 100 trace 37 1 62 99 1 18 80 2 20 80 19 80 1 20 80 6.4 93.2 0.3 6.7 93.2 Substituent CH 3 58 4 38 96 4
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22- 22-4 Di- and Polysubstitution Di- and Polysubstitution Orientation: certain substituents direct preferentially to ortho & para positions; others to meta positions substituents are classified as either ortho-para directing ortho-para directing or meta directing meta directing toward further substitution Rate certain substituents cause the rate of a second substitution to be greater than that for benzene itself; others cause the rate to be lower substituents are classified as activating activating or deactivating deactivating toward further substitution
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22- 22-5 Di- and Polysubstitution Di- and Polysubstitution -OCH 3 is ortho-para directing -NO 2 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%)
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22- 22-6 Di- and Polysubstitution Di- and Polysubstitution Weakly  activating 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 2 NO 2 NH 3 + CF 3 CCl 3 C N O O O O O O
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22- 22-7
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