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Electrophilic Aromatic Substitution Reaction Lab Report

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Lewis-Acid Catalyzed electrophilic aromatic substitution reactions of thionyl chloride, and benzene. Introduction: Organic sulfoxides, especially diphenyl sulfoxide (Ph2SO), are useful synthetic reagents (Kaczorowska et al., p. 8315). Diphenyl sulfoxide has been used in catalytic oxidation of alkyl sulfides to sulfoxides (Arterburn & Nelson, p.2260). They also play an important role as therapeutic agents. Examples include anti-ulcer, antibacterial, antifungal, anti-therosclerotic, anthelmintic, antihypertensive, and cardiotonic agents, as well as, psychotonics and vasodilators (Kaczorowska et al., p. 8315). Diphenyl sulfoxide is also used as a reagent in the formation of glycosidic bonds (Garcia, Pool, & Gin, p.1). This involves an in situ …show more content…

This difference can lead to differing yields in the products of interest. In this case, what is to be determined is which Lewis-acid catalyst produces higher yields of diphenyl sulfoxides. Previously, aluminum-chloride-catalyzed Friedel-Crafts (EAS) reactions of thionyl chloride (SOCl2) with benzene (PhH) were conducted. Thionyl chloride readily combines with AlCl3 to produce diphenyl sulfoxide, mainly when mixed in 2:1:1 molar ratio (Sun, Haas, McWilliams, Smith, & Leaptrot, p.1). Thionyl chloride and aluminum chloride combine via a OAl coordination bond forming 1:1 zwitterionic adduct Cl2SO+--AlCl3 (Sun, Haas, Sayre, & Weller, p.1). What has not been performed yet is a similar reaction involving iron(III) chloride (FeCl3). The FeCl3-catalysed Friedel-Crafts (EAS) reactions with thionyl chloride and benzene will optimistically produce different yield percentages of diphenyl sulfoxides and diphenyl sulfides than that of the AlCl3-catalysed reactions. Hopefully, the study of these reactions will lead to better knowledge of how Lewis-acid catalysts play a role in electrophilic aromatic substitution reactions. The reactions will be performed at various temperatures (-10°C, 0°C, 25°C,45°C, 70°C) and have differing mole ratios (2:1:1, 3:1:1), which will produce dissimilar product yields. The reagents will also be mixed in various ways, and the purpose of this is to see which order of mixing …show more content…

8315). Furthermore, the organic sulfoxides have an important function as therapeutic agents and these include: anti-ulcer, antibacterial, antifungal, and cardiotonic agents, as well as, psychotonics and vasodilators (Kaczorowska et al., p.8315). Examining these various reactions, which produce sulfoxides, will be important for educational purposes: providing alternate ways to obtain sulfoxides, and to distribute more knowledge on Lewis-Acid catalysts and their interaction in EAS reactions. Lewis-acids are an important class of acids and are imperative for adolescents and even adults, who are in schooling, to learn

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