Experiment: Diels-Alder (D-A) Title: Diels-Alder Reaction (Otto and Kurt). Cycloaddition of Maleic Anhydride with Anthracene Ref: Hill, R. K.; Barbaro, J. Experiments in Organic Chemistry (2000, 2nd Ed) pp E7-1-3. Purpose: Synthesize 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride Reagent table: revised 03/09/2010ssh lease write the answers to the following questions directly in your notebook. 1. Answer the following questions pertaining to the reaction of maleic anhydride and 1,3butadiene: a) Specify the conformation required to enable a 1,3-diene to undergo the Diels-Alder reaction. (3 pts) b) Which conformation of 1,3-butadiene, s-cis or s-trans, is thermodynamically preferred and why? (3pts) c) Why does 1,3-butadiene react more rapidly with maleic anhydride than with another molecule of itself? (3 pts) 2. In the Diels-Alder experiment, the solution containing the desired cycloadduct product is to be cooled slowly. a) Briefly explain the reason for cooling the solution slowly. (3 pts) b) What technique is to be used to effect slow cooling of the solution of product? ( 3 pts) 3. What action should you take if maleic anhydride gets in your eyes? (3 pts) Experiment: Diels-Alder (D-A) Title: Diels-Alder Reaction (Otto and Kurt). Cycloaddition of Maleic Anhydride with Anthracene Ref: Hill, R. K.; Barbaro, J. Experiments in Organic Chemistry (2000, 2nd Ed) pp E7-1-3. Purpose: Synthesize 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride Reagent table: revised 03/09/2010ssh lease write the answers to the following questions directly in your notebook. 1. Answer the following questions pertaining to the reaction of maleic anhydride and 1,3butadiene: a) Specify the conformation required to enable a 1,3-diene to undergo the Diels-Alder reaction. (3 pts) b) Which conformation of 1,3-butadiene, s-cis or s-trans, is thermodynamically preferred and why? (3pts) c) Why does 1,3-butadiene react more rapidly with maleic anhydride than with another molecule of itself? (3 pts) 2. In the Diels-Alder experiment, the solution containing the desired cycloadduct product is to be cooled slowly. a) Briefly explain the reason for cooling the solution slowly. (3 pts) b) What technique is to be used to effect slow cooling of the solution of product? ( 3 pts) 3. What action should you take if maleic anhydride gets in your eyes? (3 pts)