1. Chapter 29 Friedel-Crafts Alkylation of Bezene

2. Purpose In this experiment a mixture of benzene and alkyl chloride is treated with AlCl 3 (Lewis acid). The dialkyl product is isolated by adding water and extracting.In this experiment a mixture of benzene and alkyl chloride is treated with AlCl 3 (Lewis acid). The dialkyl product is isolated by adding water and extracting. The organic phase is then washed, dried and evaporated to give oily product which should solidify upon cooling.The organic phase is then washed, dried and evaporated to give oily product which should solidify upon cooling.

3. Reaction Mechanism The Friedel-Crafts alkylation is a typical electrophilic substitution reaction. The electrophile is t-butyl cation generated by the reaction of alkyl halide and Lewis acid. The dialkyl product is formed stepwise.The Friedel-Crafts alkylation is a typical electrophilic substitution reaction. The electrophile is t-butyl cation generated by the reaction of alkyl halide and Lewis acid. The dialkyl product is formed stepwise.

4. Comments Follow pp. 438-440(microscale).Follow pp. 438-440 (microscale). Follow the lab handout for all experimental procedures. Wearing rubber gloves is absolutely necessary during this lab! You will work with toxic, carcinogenic and corrosive compounds.Follow the lab handout for all experimental procedures. Wearing rubber gloves is absolutely necessary during this lab! You will work with toxic, carcinogenic and corrosive compounds. Perform IR analysis of the product.Perform IR analysis of the product. Calculate yield. Moderate yields should be achieved.Calculate yield. Moderate yields should be achieved. (Moles Product / Moles Starting Material) x 100 = % Yield

5. Safety Benzene is highly flammable, irritating to eyes and skin and may cause lung damage if swallowed. Also, as shown on animal models, may cause cancer and heritable genetic damages by prolonged exposure. Do not swallow, do not inhale and avoid contact with eyes and skin. Wear gloves and handle with extreme caution.Benzene is highly flammable, irritating to eyes and skin and may cause lung damage if swallowed. Also, as shown on animal models, may cause cancer and heritable genetic damages by prolonged exposure. Do not swallow, do not inhale and avoid contact with eyes and skin. Wear gloves and handle with extreme caution. Aluminum chloride is corrosive, wear gloves and handle with care.Aluminum chloride is corrosive, wear gloves and handle with care.