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Organic Chemistry Fourth Edition - PageOut_20620：有机化学第四版- pageout_20620
12.15 Multiple Substituent Effects The Simplest Case all possible EAS sites may be equivalent Another Straightforward Case directing effects of substituents reinforce each other; substitution takes place ortho to the methyl group and meta to the nitro group Generalization regioselectivity is controlled by the most activating substituent The Simplest Case all possible EAS sites may be equivalent When activating effects are similar... substitution occurs ortho to the smaller group Steric effects control regioselectivity when electronic effects are similar position between two substituents is last position to be substituted 12.16 Regioselective Synthesis of Disubstituted Aromatic Compounds Factors to Consider order of introduction of substituents to ensure correct orientation Synthesis of m-Bromoacetophenone Which substituent should be introduced first? Synthesis of m-Bromoacetophenone If bromine is introduced first, p-bromoacetophenone is major product. Synthesis of m-Bromoacetophenone Factors to Consider order of introduction of substituents to ensure correct orientation Friedel-Crafts reactions (alkylation, acylation) cannot be carried out on strongly deactivated aromatics Synthesis of m-Nitroacetophenone Which substituent should be introduced first? Synthesis of m-Nitroacetophenone If NO2 is introduced first, the next step (Friedel-Crafts acylation) fails. Synthesis of m-Nitroacetophenone Factors to Consider order of introduction of substituents to ensure correct orientation Friedel-Crafts reactions (alkylation, acylation) cannot be carried out on strongly deactivated aromatics sometimes electrophilic aromatic substitution must be combined with a functional group transformation Synthesis of p-Nitrobenzoic Acid from Toluene Which first? (oxidation of methyl group or nitration of ring) Synthesis of p-Nitrobenzoic Acid from Toluene Synthesis of p-Nitrobenzoic Acid from Toluene 8 6 8 AlCl3 O CH3COCCH3 O + CH3 CH3 CH3 CH3 CCH3 O 99% CH3 NO2 CH3 NO2 Br 86-9
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