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.
2. Draw (E)-1,3-hexadiene in its s-cis conformation.
3. Draw the LUMO of 1,3-butadiene.
4. Which of the following represents the highest occupied molecular orbital for the
conjugated pi system in Vitamin D3? Circle the right answer
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.
6. Provide a detailed, stepwise mechanism for the reaction shown below.
7. Provide the two major organic products of the following reaction.
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.
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?
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.
11. Provide the major resonance structures of the ion which results when the most acidic
hydrogen of cyclopentadiene is lost.
12. Is the molecule below aromatic, antiaromatic, or nonaromatic?
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.
14.Provide the structure of the major organic product(s) in the following reaction.
15.Draw a mechanism for the following reaction.

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