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1. Name the following compounds: a. b. c. OH 2. Draw the structures of the following compounds: a. 1,5-hexadiene b. m-nitrobenzoic acid c. 2,4,6-trinitrotoluene ____________________________ ____________________________ _____________________________ 3. Give the major products of the following reactions: a. b. c. d. 1. O3 2. Me2S Br Br 1. 3 NaNH2 2. H3O+ 1. nBuLi O 2. + H 3. H3O+ Cl FeCl3 O 4. Pick appropriate reagents to synthesize the following products. a. b. Br c. 5. You found a bottle in the lab labeled “nitrophenol”. How can you determine whether it is o-, m-, or p-nitrophenol? 6. Draw the major organic product(s) and show the mechanism of the following reactions. If multiple products are formed in significant amounts, draw all of them. a. HBr SO3H b. MgBr 2. H3O+ O 1. 7. Circle the aromatic compounds: N 8. Add the reagents and draw the structure of the major mononitration product(s) for this compound. O Show the formation of the strong electrophile. 9. Sort the following molecules by a. Reactivity towards Electrophilic Aromatic Substitution (1 = very reactive, 4 = not very reactive, deactivated) _____ _____ NH2 _____ ______ NO2 Cl b. Acidity (1 = most acidic, 4 = least acidic) _____ ______ _____ _____ O OH 10. The figure below shows the orbitals involved in the concerted movement of the 6 pi electrons in the formation of the Diels-Alder adduct. This process is allowed (=possible) due to the matching symmetry of the terminal diene HOMO orbitals with those of the dienophile LUMO orbitals (on the left). Determine based on this requirement for an allowed process, whether the reaction shown on the right is possible. Draw the orbitals into the structures on the right to support your answer. Reaction on the right allowed or not: ____________ OH

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