1. Show how the carbon p orbitals overlap to form the lowest energy π molecular orbital of 1,3-butadiene. Answer: 2. Draw (E)-1,3-hexadiene in its s-cis conformation. Answer: 3. Draw the LUMO of 1,3-butadiene. Answer: 4. Which of the following represents the highest occupied molecular orbital for the conjugated pi system in Vitamin D3? Circle the right answer A) B) C) D) 5. When 3-bromobut-1-ene is heated in a good ionizing solvent, reactions occur through a carbocation intermediate. Draw all reasonable resonance contributors of this cation and indicate which is the major contributor. Answer: 6. Provide a detailed, stepwise mechanism for the reaction shown below. Answer: 7. Provide the two major organic products of the following reaction. Answer: 8. In the diene shown below, there are two possible double bonds that could react when 1 eq. of HBr is added. However, the double bond labeled "A" reacts preferentially to give the major product. Using resonance structures, justify this observation. Answer: 9. When toluene is treated with bromine (shown below), the bromine doesn't react with the double bond to form a viscinal dihalide, but instead a substitution of one of the benzylic hydrogens takes place. Why? Answer: 10. Provide a diagram which depicts the relative energies of the π molecular orbitals of benzene. Show which molecular orbitals are filled in benzene's ground state. Answer: 11. Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost. Answer: 12. Is the molecule below aromatic, antiaromatic, or nonaromatic? Answer: 13.Provide a detailed, stepwise mechanism for the reaction of benzene with Br2 and FeBr3. Make sure to include the activating reaction between Br2 and FeBr3 in your mechanism. Answer: 14.Provide the structure of the major organic product(s) in the following reaction. Answer: 15.Draw a mechanism for the following reaction. Answer:
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