1. (15 points) Write finish names for each the the following, including stereochemistry if it is especially shown.

You are watching: Indicate the product formed on nitration of each of the following compounds

a)

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m-nitrostyrene or 3-nitrostyrene

b)

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2-phenylpyrrole

c)

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3-chloro-5-ethylphenol

d)

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1,8-dibromonaphthalene

e)

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3-fluoro-4-phenylbenzoic acid

2. (15 points) create all the resonance creates for the intermediate that would certainly be created in the shown reactions. A final product or mechanism is not required - just the resonance forms.

a)

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b)

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c)

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3. (15 points) complete each of the adhering to reactions by adding the lacking part: either the starting compound, the vital reagents and also conditions, or the final major product. Show stereochemistry if the is specific.

a)

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b)

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c)

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d)

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e)

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4. (20 points) Write man-made sequences that might be supplied to prepare the complying with compounds.

a) (start with benzene, acetylene, and also methane)

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b) (start with benzene plus whatever other organic materials you need)

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5. (15 points) compose a finish mechanism because that the nitration that chlorobenzene. Present all steps and also all resonance forms for the intermediary involved. Just present the pathway come the significant product. Decide which will be the major product based upon the partial rate factors for ortho (0.029), meta (0.0009), and also para (0.137).

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6. (10 points) The orbitals shown listed below represent the HOMO and also LUMO that a delocalized π system. (HOMO = greatest occupied molecular orbital, LUMO = lowest unoccupied molecule orbital)


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LUMO
(top) / HOMO (bottom)


a) (2 pts) label which is the HOMO and also which is the LUMO.

b) (3 pts) draw the framework of the compound for i m sorry these space the HOMO and also LUMO. Is the a cation, neutral, or one anion?

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(Note - over there are 5 p orbitals and also only 4 electrons - based on the HOMO)

c) (3 pts) show the pattern of π power levels because that this compound, consisting of the number of electrons in each MO. Designate i m sorry MOs are the HOMO and also LUMO in this diagram.

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d) (2 pts) draw the orbit symmetry because that the lowest energy π molecular orbital.

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7. (10 points) The pattern of molecule orbital power levels shown below represents a delocalized π system.

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LUMO
(top) / HOMO (middle)

a) (2 pts) label the HOMO and the LUMO on the diagram above.

b) (3 pts) draw the structure of the compound described by this pattern of MOs. Is that a cation, neutral, or one anion?

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(Note - there are five p orbitals in a ring - based upon the paired energy levels)

c) (3 pts) Is this compound aromatic? Explain, indicating every of the criteria of Huckel’s Rule.

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Yes. It has 6 electrons (a 4n+2 number) in a planar, constant cyclic range of p orbitals.