Experiment 32: friedel crafts alkylation Introduction: The purpose of the lab was to understand the electrophilic aromatic

substitution reaction, friedel crafts alkylation. The reaction forms a new C-C bond between the aromatic ring and the alkyl group. In this lab, the 7 Procedure: 1.5g (.006 ml) triphenylmethanol was measured into a 250 mL Erlenmeyer flask. 4.5 mL anisole and 43 mL of glacial acetic acid was added. The flask was swirled and 4.3 mL of concentrated sulfuric acid was added and mixed. The flask was covered and stored for a week. 100 mL of distilled water was added, and it was buchner filtered. It was washed with a few mL of diethyl ether. The residue was collected and weighed, and the melting point was taken. FLOWCHART Table of chemicals: Chemical Triphenylmethanol Anisol Glacial acetic acid Conc. Sulfuric acid Water Diethyl ether Crude pmethoxytetraphenylmethane Mechanism:

Quantity 1.513 g 4.5 mL 43 mL 4.3 mL 100 mL 3.8 mL 1.794 g

Molecular weight 260.33 108.14 60.05 98.08 18.02 74.12 350.461

Melting point (actual) ------198-200

Melting point (experimental) ------195.2-196.7

Observations: Triphenylmethanol was a white, grainy powder. Anisole was clear and colorless, but not viscous. Glacial acetic acid was pungent, clear, colorless, and not viscous. Sulfuric acid was clear and colorless. When sulfuric acid and anisole combined, the solution was a urine color and cloudy. When H2SO4 was added to the flask, the solution turned a dark

orange-blood color. After storage, the solution was crystallized; it was red with tiny orange pineapples floating in it. After adding the wawter, the solution looked like pulpy orange juice. After buchner filtration, the filtrate was lemon yellow and slightly opaque; the residue resembled damp ramen noodle pieces. The diethyl ether wash whitened the residue. After drying, the residue had an orange tint. Percent yield: ( )( )( )

Results: Talk about percent yield and mass o Percent yield is 88.1%; mass is 1.794 g; actual mass 2.04 o Should be lower due to crudeness Talk about melting point; actual vs. experimental o Experimental: 198-200 for crude o Actual: 195.2-195.8 o Impurities: water, sulfuric acid o Lower melting point due to presence of impurities: a highly pure substance would be symmetrical, so it would have a higher melting point. However the impurity causes asymmetry in the molecules structure, so less energy is required for the molecule to reach its melting point. The large melting point range indicates impurities else it would be a sharp point. Talk about friedel crafts reaction o New C-C bond is formed between the aromatic ring and the alkyl group o Carbocation is what attaches to the benzene ring to form the product o Limitations: vinyl halides and aryl halides o Hydride and alkyl shifts cause more than one product; carbocation rearrangements