Problems Set - Meeting #7

1. A student dissolves 1.0 g of tetraphenylcyclopentadienone and 0.5 g of anthranilic acid in 10 mL of tetrahydrofuran and then adds 1.0 mL of isopentyl nitrite.

a. How much carbon monoxide (in units of mL) is given off (assume reaction goes to completion) (Hint: CO might be treated as an ideal gas here!)?

b. Which size of flask would be appropriate for the reaction?

c. What do you observe during this reaction?

2. Benzyne is formed in "in-situ" in this reaction. What does this term mean? Why is this strategy used in this experiment?

3. The reaction of butadiene with cyclohexene is relatively slow and requires high temperatures, while the reaction of acrylonitrile with 1,2,3,4-Tetramethylcyclopentadiene can be carried out at much lower temperatures. Explain these observations.

4. The reaction of cyclopentadiene with maleic anhydride affords the endo-product at low temperatures.

a. Draw the structure of the product of this reaction.

b. Why is the endo-product observed as major product under these conditions?

5. Why is 1,2-dimethoxyethane used in this reaction?

6. A UV-Vis spectrum is also obtained for the compound obtained in this week's experiment.

a. Why does the procedure ask to use a quartz cuvette and not a plastic cuvette like before?

b. What do you expect to change in comparison with last week's product?

c. Which concentration is needed for the UV-Vis characterization of the TPN?