benzenesg - Benzenes 1 Copyright, Arizona State University...

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Unformatted text preview: Benzenes 1 Copyright, Arizona State University Copyright, Arizona State University Reactions of Benzenes Electrophilic Aromatic Substitution (more...) 1 Notation Structures and Nomenclature disubstituted notation... 1,2 = ortho- xylene 1,3 = meta- xylene 1,4 = para- xylene IUPAC: uses numbering system • number round the ring to give substituents get the lowest numbers possible as usual • all other things equal (and ONLY when all other things are equal), then do it alphabetically NO 2 Br NO 2 4-Bromo-1,2-dinitrobenzene 1 2 3 4 Some aromatic compounds have their own IUPAC names: CH 3 CO 2 H OCH 3 OH NH 2 CHO anisole styrene benzoic acid toluene phenol benzaldehyde aniline naphthalene * * * * * * you need to be able to name substituted versions of these for test purposes 2-bromo-6-nitrobenzoic acid carbon #1 by definition 2 6 named as substituted benzoic acid 5-ethyl-2-nitrophenol 2 5 named as substituted phenol C O OH O 2 N Br OH O 2 N CH 2 CH 3 carbon #1 by definition • drawing structures of benzenes Need to use this to keep track of electrons in mechanisms Accurate, good shorthand Benzenes 2 Copyright, Arizona State University Copyright, Arizona State University Benzene PROBLEMS Benzene Nomanclature Provide a IUPAC name for each of the following 1 (standard) CO 2 H Br Cl Answer Correct Y / N 2 (standard) CH 2 CH 2 CH 3 Br Answer Correct Y / N 3 (standard) CH 3 Br I F Answer Correct Y / N 4 (standard) CH 2 CH 3 H 3 C Br Answer Correct Y / N 5 (standard) CH 3 O 2 N NO 2 NO 2 Answer Correct Y / N 6 (standard) CH 3 F CH 3 Answer Correct Y / N 7 (standard) CH 2 CH 3 O 2 N Br Answer Correct Y / N 8 (standard) Cl F Br Answer Correct Y / N 9 (standard) OH F NO 2 Answer Correct Y / N 10 (standard) Et Me Pr Pr Answer Correct Y / N Remember, UNDERSTANDING is different from DOING!!! Benzenes 2 Copyright, Arizona State University Copyright, Arizona State University Benzene PROBLEMS Benzene Nomanclature Provide a IUPAC name for each of the following 1 (standard) CO 2 H Br Cl Answer Correct Y / N 2 (standard) CH 2 CH 2 CH 3 Br Answer Correct Y / N 3 (standard) CH 3 Br I F Answer Correct Y / N 4 (standard) CH 2 CH 3 H 3 C Br Answer Correct Y / N 5 (standard) CH 3 O 2 N NO 2 NO 2 Answer Correct Y / N 6 (standard) CH 3 F CH 3 Answer Correct Y / N 7 (standard) CH 2 CH 3 O 2 N Br Answer Correct Y / N 8 (standard) Cl F Br Answer Correct Y / N 9 (standard) OH F NO 2 Answer Correct Y / N 10 (standard) Et Me Pr Pr Answer Correct Y / N Remember, UNDERSTANDING is different from DOING!!! Benzenes 3 Copyright, Arizona State University 2 Miscellaneous Reactions of Benzenes 2.1 Reduction : Addition of Hydrogen (more…) Catalytic addition of H 2 : forcing conditions required to add H 2 to the benzene ring (breaks aromaticity) Harder to reduce benzene ring - aromatic H 2 Pt/1000 psi H 2 Pd/C 50 psi Side Chain Reduction O Zn(Hg) HCl, H 2 O reduced to alkane H H HO NaBH 4 /EtOH reduced to alcohol (Clemmenson reduction) π-withdrawing π-donating • the first reaction we have already seen...
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This note was uploaded on 01/07/2012 for the course CHM 234 taught by Professor Iangould during the Spring '12 term at Appalachian State.

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benzenesg - Benzenes 1 Copyright, Arizona State University...

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