Transcription of The Friedel-Crafts Reaction - Open Computing Facility
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The Friedel-Crafts Reaction - Open Computing Facility
UC Berkeley College of ChemistryChemistry 112 BOrganic ChemistryThe Friedel-Crafts ReactionAuthor:JonathanMelvilleGraduate Student Instructor:RebeccaTrianoFebruary 27, 201411 IntroductionFriedel-Crafts alkylation is an important method for adding alkyl chains to aromatic ringsthrough the use of a strong Lewis acid, generally AlCl3or FeCl3, as a catalyst. Thoughthe Reaction has some limitations (namely the potential forcarbocation rearrangementlimiting the types of alkyl chains that can be substituted),its relative simplicity makesit an important tool when dealing with aromatic the Friedel-Crafts mechanism has been known for overa century[1], the sheersimplicity of the process means it is frequently the best alkylation Reaction is thus through sheer ubiquity that research on the parameters of the Reaction isstill ongoing (mostly revolving around the specific substituents and catalysts that canparticipate in the Reaction , according to a 2011 review[1]).
3 Experimental 4,4’-Di-tert-butylbiphenyl (4): A flame-dried reaction tube connected to an HCl gas trap was charged with biphenyl (0.166 g, 1.08 mmol), t-butyl chloride (0.50 mL, 4.5 mmol), dichloromethane (0.50 mL), and a 4 mm2 square of aluminum foil with the aluminum oxide coating scratched. Once
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