9/23/2015
(Laura Williams)
(Jasmine Threadcraft)
Alice Chon

Friedel-Crafts Alkylation

Friedel-Crafts Alkylation Reaction:

Abstract

This experiment demonstrates a synthesis of a 1,4-di-t-buytl-2,5-dimethoxybenzene by reacting 1,4-dimethoxybenzene with a tertiary-butyl alcohol with the presence of a Lewis acid, sulfuric acid (H2SO4), called a Friedel-Crafts mechanism. This reaction yield a product of 67.96% yield and a melting point starting at 103˚C and a complete melting point around 106˚C. Am HNMR spectrum revealed that the end product of 1,4-di-t-buytl-2,5-dimethoxybenzene was synthesized successfully. The small range of the melting point indicated the good purity which also indicated the formation of a Friedel-Crafts reaction.

Introduction

Charles Friedel and James Crafts were the first to develop a method that alkylates and acylates aromatic rings in an easy synthesis. This is one of the oldest methods of forming C-C bonds by functioning unbiased arenas with unactivated C-H bonds. In their research, they isolated a pentylbenzene after a reaction of 1-chloropentane and benzene using a stoichiometric amount of a Lewis Acid promoter, AlCl3. With this success, many Lewis acids have been tested throughout the years in the Friedel-Crafts alkylation to develop more synthetic use. Research is still ongoing and being done today of finding more efficient and easily executed Lewis acids to produce non-toxic, metal free by-products.

Table of Reagents and Product Quantity

|Name |Molar Mass (g/mL) |
|acetic acid |Highly flammable. irritating vapor generated when heated. breathing |
|