Week 7 worksheet

Week 7 worksheet - justify why aniline brominates at the...

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1 of 2 Organic Chemistry II Week 7 worksheet Not for credit Draw an example of the key electrophile for each of the following types of electrophilic aromatic substitutions: Bromination Nitration Friedel-Crafts alkylation Friedel-crafts acylation Draw the mechanism of the Friedel-Crafts acylation of the the reaction shown below. Show the formation of the acylium ion, followed by electrophilic aromatic substitution. AlCl 3 + O Cl O Aniline and nitrobenzene both contain a nitrogen substituted benzene ring; however, bromination of each of these compounds results in dramatically different products. Use resonance structures of the cation intermediate of each to
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Unformatted text preview: justify why aniline brominates at the ortho/para positions and nitrobenzene brominates in the meta position. Given that bromination of aniline results in 2-bromoaniline and 4-bromoaniline, how could you prepare 3-bromoaniline? NH 2 Br 2 FeBr 3 NH 2 Br NO 2 Br 2 FeBr 3 NO 2 Br HNO 3 H 2 SO 4 N AlCl 3 O Cl 2 of 2 O SO 3 H 2 SO 4 O CF 3 AlCl 3 Cl Br 2 FeBr 3 NH O Cl HNO 3 H 2 SO 4 Place the following reagents in the correct order to best prepare the following compound in the reaction shown: Cl 2 /FeCl 3 , HNO 3 /H 2 SO 4 , CH 3 C(O)Cl, Ni/H 2 , Cl NH O HNO 3 /H 2 SO 4 , HNO 3 /H 2 SO 4 , NaOCH 3 /CH 3 OH, Br 2 /FeBr 3 , O NO 2 NO 2...
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Week 7 worksheet - justify why aniline brominates at the...

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