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1) Predict the major product of each of the following Diels-Alder Reactions: HO O O O O CN 2) What compound could be used to make the product below in an intramolecular Diels-Alder Reaction? 3) Circle the 3 most electrophilic carbons on the compound below: 4) Circle the 3 most nucleophilic atoms on the compound below: 5) Name the compounds below: 6) Circle any aromatic compounds below: 7) Rank the following in order of acidity. 1=least acidic, 5=most acidic. 8) Show the kinetic and thermodynamic products of the hydrohalogenation reactions below. Indicate the conditions which would lead to each product. 9) Rank the following in order of stability. 1=least stable, 4=most stable. 10) Draw the most stable resonance structure of the following molecule. Include the arrow pushing mechanism which leads to it. Use structures I-V for questions 11-16. 11) Compound I has a heat of hydrogenation of approximately a. 29 kJ/mol b. -29 kJ/mol c. 50 kJ/mol d. 55 kJ/mol e. -55 kJ/mol 12) Hydrogenation of compound II releases approximately 2x as much heat as compound I. True/False? 13) Compound II has 2 double bonds, compound III has 4 double bonds. Which of the following is true? a. Compound III has twice the heat of hydrogenation as compound II. b. Compound III has 50% the heat of hydrogenation as compound II. c. Compound III releases more than twice the heat as compound II upon hydrogenation. d. Compound III releases less than twice the heat as compound II upon hydrogenation. 14) Which compound above can undergo a 1,4-thermodynamic addition of HBr under elevated temperatures? 15) Multiple equivalents of Br2 can be added to compound III without the use of a catalyst. True/False? 16) Which compound releases the most heat upon hydrogenation? Explain your reasoning. 17) Design an optimal synthetic route to prepare the product below starting with benzene: 18) Predict the product of the following reactions: S CH3CH2Cl, AlCl3 O 2) Br2, FeBr3 1) CH3CO2Cl HN SO3, H2SO4 H2 Pt 19) Design a synthetic scheme to complete the following conversion: 20) Predict the products of the following reactions. If there are competing reactions, show both products and circle the major one. OH D I OH Br I H3O+ OC NaOCH3 Br H2SO4 heat NaSCH3 HBr OK O Br OH 21) Design a synthetic scheme to complete the conversion below:

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