lecture 22.2

lecture 22.2 - 22-22-1Organic Organic...

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Unformatted text preview: 22-22-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson22-22-2Reactions of Reactions of Benzene and itsBenzene and itsDerivativesDerivativesChapter 22Chapter 2222-22-3Di- and PolysubstitutionDi- and PolysubstitutionOrientation on nitration of monosubstituted benzenesOCH3ClBrCOOHCNNO2orthometaparaortho +parameta44-5599trace70-30100trace371629911880220801980120806.493.20.36.793.2SubstituentCH35843896422-22-4Di- and PolysubstitutionDi- and PolysubstitutionOrientation:certain substituents direct preferentially to ortho & para positions; others to meta positionssubstituents are classified as either ortho-para directingortho-para directingor meta directing meta directing toward further substitutionRatecertain substituents cause the rate of a second substitution to be greater than that for benzene itself; others cause the rate to be lowersubstituents are classified as activatingactivatingor deactivatingdeactivatingtoward further substitution22-22-5Di- and PolysubstitutionDi- and Polysubstitution-OCH3is ortho-para directing-NO2is meta directingOCH3HNO3CH3COOHOCH3NO2OCH3NO2H2Op-Nitroanisole (55%)o-Nitroanisole (44%)Anisole+++COOHHNO3H2SO4NO2COOHCOOHNO2NO2COOH100 Cm-Nitro-benzoicacid(80%)Benzoicacid+++o-Nitro-benzoic acid(18%)p-Nitro-benzoicacid(2%)22-22-6Di- and PolysubstitutionDi- and PolysubstitutionWeakly activatingWeakly deactivatingModerately activatingStrongly activatingNH2NHRNR2OHNHCRNHCArOROCArOCRRFClBrI::::Strongly deactivatingModerately deactivatingCHOOCRCOHSO3HCOROCNH2NO2NH3+CF3CCl3CNOOOOOO22-22-7Di- and PolysubstitutionDi- and PolysubstitutionFrom the information in Table 21.1, we can make these generalizationsalkyl, phenyl, and all other substituents in which the...
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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 22.2 - 22-22-1Organic Organic...

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