Pre-Lab_ Diels-Alder

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Pre-Lab: Diels-Alder Reaction: 9,10- α,β-succinic acid anhydride Reference Handout: Schoffstall, A.; Gaddis B.; Drueling, M.; Melting Point; Microscale and Miniscale Organic Chemistry Laboratory Experiments , McGraw-Hill, (2011), 271-275; 278-280. Reading assignment: Mohrig, J.R.; Hammond, C.N.; Schatz, P.F.; Techniques in Organic Chemistry; Freeman, New York, 2011, 59-61 (3 rd Edition) Review Filtration technique: Mohrig, J.R.; Hammond, C.N.; Schatz, P.F.; Techniques in Organic Chemistry; Freeman, New York, 2011, 114-112 (3 rd Edition) Review Thin Layer Chromatography : Mohrig, J.R.; Hammond, C.N.; Schatz, P.F.; Techniques in Organic Chemistry; Freeman, New York, 2011, 221-233 (3 rd Edition) Experiment Notes: Work on fume hood. Characterization will be done by MP and TLC; If no melting is observed at 215 o C, then your product shall be considered pure. Melting Point and TLC shall be recorded in the week after the experiment is done; leave your solids to dry until next lab period. Record the IR spectra for your final product.
Copy and paste structures from ChemDraw; (0.1 points/box) Use Pictograms from each chemicals SDS for the Hazard / Toxicity. Please refer to the information inside the “Laboratory Safety Materials” folder on your course Blackboard page. (0.1 points/box) For Chemical Disposal, identify the chemical physical state (solid, liquid, gas) and use the Chemical Disposal Information inside the “Laboratory Safety Materials” folder on your course Blackboard page. (0.1 points/box) Table of Reagents: Compound Structure MP ( o C) MW (g/mol) Mass (g) Volume (mL) mols Hazard /Toxicity Disposal Anthracene CAS # 120-12-7 217 178.2 0.89 Not required 0.004994 Environment Hazard, Health Hazard solid maleic anhydride CAS # 108-31-6 53 98.06 0.49 Not required 0.004691 Corrosive, health hazard, harmful Solid xylene CAS# 1330-20-7 Not required 106.18 Not required 12 Not required Harmful, flammable Organic Hexanes CAS # 73513-42-5 Not required 86.17 Not required 1-2 Not required Harmful, flammable Organic 9,10- dihydroanthracene- 9,10-α,β-succinic acid anhydride CAS# 5443-16-3 261-262 276.26 1.30 1.30 0.004705 Harmful solid Calculations 1. Show your mols calculations work Anthracene: 0.89g * (1mol/178.2g) = 0.004994 mol Maleic Anhydride: 0.46g * (1mol/98.06g)= 0.004691 mol 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride:
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Diels-Alder reaction mol amount of anthracene used O.035g 0.2529 0.2145 amount of maleic anhydride used amount of crude product obtained amount of purified product obtained recrystallization recovery, % product theoretical yield crude product yield, % purified product yield, % Write the equation for the overall reaction: Product Characterization crude product purified product melting range, °C The product will be characterized by IR. Please label the pertinent absorbances on the spectrum of your product, as well as the provided spectrum of the starting materials, anthracene and maleic anhydride.
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