CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 – Aromatics1. AromaticityDetermine if the following species are aromatic or non-aromatic.NNNHSN2. Nomenclaturea. Give the common names for the following compounds. OH N(CH3)2CH3CO2HCHOb. Give the proper systematic IUPAC names for the following compounds. OCH3NCH3CH3OHNH21CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 – AromaticsOCH3CO2HCH3CH2ClHOOCH2CH3BrFFIBrNO2OCH2CH2CH3A B CDEFc. Using the structures (A-F) above, answer the following questions.What is the positional relationship between the two substituents in compound A? ___________What is the positional relationship between the two substituents in compound D? ___________What is the positional relationship between the bromine and iodine in compound F? _________3. Reactions of Benzene2CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 – AromaticsDraw the major product or products of each reaction. Br2, FeBr3H2SO4CH3CHBrCH2CH3HNO3, H2SO4CH3CH2ClAlCl3AlCl33CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 – Aromatics1) AlCl31) CH3COCl, AlCl32) H2OH2SO4CH3CH2CH=CH2H2SO43-hexanolCH3CH2COCCH2CH3O O1) benzene, heat2) H2O2) H2OCl4. MechanismsProvide complete arrow-pushing mechanisms for the following reactions.a.4CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 – AromaticsCl2, FeCl3Clb.HNO3, H2SO4NO25. Substituent Effects on EAS Reactionsa. Determine if the following substituents would activate or deactivate benzene in an EAS reaction. Then determine if the substituent would be an ortho/para or meta director.5CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 – AromaticsCH2CH3CCH3OCH2CF3CF3OHOCCH3OOCH3N(CH3)2CO2CH3NHCCH3OCN Clb. For each set, rank the substituents in order of their effect on the rate of an EAS reaction of benzene (1 strongest activating to 4 strongest deactivating.CH2CH2CH3OCCH3OOCH3N(CH3)2CO2CH3CNClCH2CH3SET1SET26. EAS Reactions of Substituted BenzenesDraw the major product or products of each reaction. 6CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 – AromaticsBr2, FeBr3H2SO4CH3CH2ClHNO3, H2SO42) H2OAlCl3Cl2, FeCl3H2SO4HNO3, H2SO4CH3CH2CH2ClAlCl3CH3NO2ClOCH3NHCCH3O1) CH3COCl, AlCl3CCH3OOHCH3CH3NO2CO2CH3BrCH2CH3CF3H2SO47. Tandem ReactionsShow the sequence of reactions that would be used to form the target compound from benzene.a.7CHEM 310 - Dr. HartelWinthrop UniversityProblem Set 12 –
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