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Winthrop CHEM 304 - The Friedel-Crafts Acylation

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Winthrop University Organic Chemistry Lab IIDepartment of Chemistry CHEM 304The Friedel-Crafts AcylationThe Friedel-Crafts acylation is an example of an electrophilic aromatic substitution(EAS) reaction. It is an excellent way to introduce a carbon chain to an aromatic ring,and is thus of great synthetic value.In this experiment, you will perform a Friedel-Crafts acylation of an unknown substitutedbenzene (C8H10) using acetyl chloride. You will then determine the identity of yourproduct, and (by reasoning) your starting unknown, using IR and 1H-NMRspectroscopies.+1) AlCl32) H2OOClOR RSafety:- Acetyl chloride and aluminum chloride are very corrosive.Procedure:Place 800 mg of AlCl3 into a 10 mL round bottom flask with a spin vane. Add 2 mL ofdichloromethane and add a Claisen adapter, rubber septum and drying tube as shownbelow. Place the assembly under the hood and add 0.5 mL of acetyl chloride dropwisevia syringe with stirring. In a 3 mL conical vial, weigh out 425 mg of your unknown.Add the unknown to your reaction flask dropwise via syringe, and stir for 30 minutes.Add 4 mL of ice water dropwise (add slowly!) via syringe and remove the septum. Add 4mL of concentrated HCl using a pipet, and stir until the solids dissolve. Transfer themixture to a separatory funnel, rinsing with 1 mL of dichloromethane. Drain the lowerorganic layer into a small Erlenmeyer flask and remove the aqueous layer. Return theorganic layer to the separatory funnel and wash with 1 mL of 5% sodium bicarbonate(vent frequently!). Drain the organic layer into a 5 mL conical vial , and dry the solutionover Na2SO4. Transfer the solution to a small pre-weighed beaker and evaporate thesolvent by warming gently under the hood. Determine the weight of your product, andobtain IR and 1H-NMR spectra.Revised 8-08Winthrop University Organic Chemistry Lab IIDepartment of Chemistry CHEM 304Write-Up:Interpret your IR specrtrum. Use the 1H-NMR to determine the structure of your product.Determine the identity of your starting material from the structure of your product.Calculate the percent yield (show the calculation) of your product.Revised 8-08Winthrop University Organic Chemistry Lab IIDepartment of Chemistry CHEM 304Questions:1. The Friedel-Crafts acylation of benzene gives only the monosubstituted product,even when an excess of catayst and acyl chloride are used. Explain why.2. The Friedel-Crafts acylation of benzene with phosgene and aluminum chloridegives a product with the formula C13H10O. What is the structure of the product?Explain how this product is formed.3. Using Student Spartan, construct a model of o-nitrotoluene. Minimize the energy.Setup the calculation for Equilibrium Geometry using the Semi-Empirical model.Also request a HOMO surface using an isovalue of 0.11. Submit the calculation.When completed, display the calculated HOMO (Highest Occupied MolecularOrbital) surface. Knowing that an electrophile will prefer to attack the atomwhere the HOMO has its largest lobe, where is the most likely site of attack? Isthis consistent with what you know about substituent directing effects in EAS?Be sure to include a printout of the model in your report.Revised


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Winthrop CHEM 304 - The Friedel-Crafts Acylation

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