Chemistry 210 - Review Sheet for Exam #4

You should be familiar with key terms listed below. You should solve the assigned problems. Some of these problems, or problems very similar, will be on the exam.  If you can solve them, you should do well on the exam.

Chapter 11 Aromatic hydrocarbons (arenes) Aliphatic hydrocarbons Benzene Kelulé structures Benzene resonance Resonance energy Hydrogenation reactions Aromatic nomenclature ortho (o) meta (m) para (p) Aromatic compounds Toluene (methyl benzene) Xylene (dimethyl benzene) Aniline (benzenamine) Phenol (benzenol) Styrene (vinylbenzene) Anisole (methoxybenzene) Benzoic acid Benzaldehyde Naphthalene Anthracene Birch reduction (dienes) Phenyl group Benzyl group Free-radical halogenation of alkylbenzenes Oxidation of alkylbenzenes Nucleophilic substitution of benzylic halides. Preparation of alkenyl benzenes Polymerization of styrene Hückel's rule (4n + 2) Heterocyclic aromatic compounds Pyridine Furan

Chapter 12 Electrophilic aromatic subsitution (EAS) EAS reaction mechanism Resonance structures Nitration (uses NO2+) Sulfonation (uses SO3) Halogenation (uses Br+) Friedel-Crafts Alkylation Carbocation electrophiles Friedel-Crafts Acylation Acylium ion electrophile Lewis acids (e.g., FeBr3 & AlCl3) Acylation-reduction Regioselectivity in EAS Resonance contributors Activating groups (o- & p-directing) Deactivating groups (m-directing) Deactivating groups (o- & p-directing) Table 12.2 Multiple substituent effects Steric hindrance Naphthalene substitution

General Review Information: Reaction mechanisms Transition states Nucleophiles Electrophiles SN1 & SN2 substitution E1 & E2 elimination Electrophilic aromatic subsitution Resonance structures Oxidation - reduction Lewis acids & bases Carbocations Creation of nucleophiles Creation of electrophiles NMR 1H (proton) NMR IR