experiment4 nitrationof aromatic compounds preparationof（experiment4 nitrationof各种芳香族化合物）.doc

EXPERIMENT 3 (Organic Chemistry II) Pahlavan/Cherif Nitration of Aromatic Compounds:? Preparation of methyl-m-nitrobenzoate Purpose Study electrophilic aromatic substitution reaction (EAS) Study regioselectivity for EAS reactions Chemicals Materials 150 – mL beaker Methyl benzoate 400-mL beaker Sulfuric acid (conc.) 125-mL flask Nitric acid (conc.) Stirring rod Ice Mel-temp Methanol Suction filtration funnel Introduction Unlike nucleophilic substitutions, which proceed via several different mechanisms, electrophilic aromatic substitutions (EAS) generally occur via the same process. Because of the high electron density of the aromatic ring, during EAS reactions electrophiles are attracted to the rings π system and protons serve as the leaving groups. Equation 1. During SN1 reactions, however, nucleophiles attack an aliphatic carbon and weak Lewis bases serve as leaving groups. Generally, EAS reactions occur in three steps, Scheme I. During Step I, the electrophile is produced, Scheme I Usually, by the interaction of a compound containing the potential electrophile and a catalyst. During Step II, the aromatic π system donates an electron pair to the electrophile, forming a σ bond ( an arenium cation) followed by deprotonation in step III in the present of a base ( HSO4-) affording the substituted arene. EAS reactions are generally second-order processes, i.e., first order in electrophile and first order in arene. Thus, Step II. is the rate-determining step (rds); rate = k2 [arene][electrophile]. Electrophilic Aromatic Substitution: Nitration of Methyl Benzoate Benzene rings are components of many important natural products and other useful organic compounds. Therefore, the ability to put substituents on a benzene ring, at specific positions relative to each other, is a very important factor in synthesizing many organic compound