Blinn College Draw Hexadiene in Its S Cis Conformation Chemistry Questions

1. Show how the carbon p orbitals overlap to form the lowest energy π molecular orbital of1,3-butadiene.
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2. Draw (E)-1,3-hexadiene in its s-cis conformation.
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3. Draw the LUMO of 1,3-butadiene.
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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.
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6. Provide a detailed, stepwise mechanism for the reaction shown below.
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7. Provide the two major organic products of the following reaction.
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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.
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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?
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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.
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11. Provide the major resonance structures of the ion which results when the most acidic
hydrogen of cyclopentadiene is lost.
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12. Is the molecule below aromatic, antiaromatic, or nonaromatic?
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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.
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14.Provide the structure of the major organic product(s) in the following reaction.
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15.Draw a mechanism for the following reaction.
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