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Ch_322b_15.16 - Chapter 15.16 lecture note

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Synthetic Applications and Strategies The influence of substituents on electrophilic aromatic substitution reactions requires special attention to the order in which they are introduced into a benzene ring in the syntheses of substituted benzenes. Example: The nitration and bromination of benzene. HNO 3 H 2 SO 4 NO 2 Br 2 Fe Br NO 2 Br Br 2 Fe HNO 3 H 2 SO 4 Br + NO 2 Br NO 2 m-bromonitrobenzene ortho para 38% 62%
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Example: The oxidation and nitration of toluene. CH 3 toluene (i) KMnO 4 , HO - , heat (ii) H 3 O + COOH HNO 3 H 2 SO 4 CH 3 CH 3 + NO 2 NO 2 HNO 3 H 2 SO 4 COOH NO 2 m-nitrobenzoic acid (i) KMnO 4 , HO - heat (ii) H 3 O + (i) KMnO 4 , HO - heat (ii) H 3 O + COOH COOH + NO 2 NO 2 ortho para All three possible positional isomers of nitrobenzoic acid may be synthesized by careful synthetic design.
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Modification of Amino and Hydroxyl Groups by Acetylation These groups are highly activating in electrophilic aromatic substitution reactions: NH 2 aniline Br 2 aqueous solution NH 2 Br Br Br 2,,4,6-tribromoaniline It is difficult to limit this reaction to monobromination.
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