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Question

Hem 2320 extra credit assignment points total. Suppose that you were asked to perform the following alkoxymercuration reaction with (S)-3-vinylcyclopentanone using the standard alkoxymercuration conditions (steps 1 and 2) shown below: Hg(OAc)2, CH3OH 2 NaBH4 Expected product: Actual product: Note: (S)-3-vinylcyclopentanone has two strong IR peaks at 1748 cm-1 and 1642 cm-1. NMR Peaks: Î´ 2.5-3 ppm (2H), 5-6 ppm (3H), and Î´ 20 ppm (PC NMR peak). (3 pts) In the first box provided above, draw the expected (stable) alkoxymercuration product if the complete alkoxymercuration reaction proceeds normally. The expected product would have a strong IR peak at 1748 cm-1 and a peak in the CNMR spectrum at Î´ 20 ppm. No IR peaks are observed in the 500-1700 cm range, nor are any peaks visible in the H NMR spectrum between 5-6 ppm. The expected product would also react with 2,4-dinitrophenylhydrazine to form a solid 2,4-dinitrophenylhydrazone derivative. If you are not 100% sure of your structure, explain what led you to choose your structure. b. (3 pts) Instead of the expected alkoxymercuration product (first box), you actually isolated a different molecule at the end of this two-step complete alkoxymercuration. The actual product shows a strong, broad IR peak at 3400 cm-1 but has no IR peak at 1749 cm-1. It lacks downfield C (>100 ppm) and H NMR ppm) peaks. The actual product does not react with 2,4-dinitrophenylhydrazine, but will react with NaH (sodium hydride) to form a gas. Draw the actual product of this reaction in the second box provided above. If you are not 100% sure of your structure, explain what led you to choose your structure. (2 pts) Explain why the actual product was formed instead of the expected product. d. (2 pts) On the basis of your explanation for part c, suggest different reagents (you may have to invent a new reagent) or reaction conditions you might use to make the alkoxymercuration give the expected product instead of the actual product formed above.

          Hem 2320 extra credit assignment points total. Suppose that you were asked to perform the following alkoxymercuration reaction with (S)-3-vinylcyclopentanone using the standard alkoxymercuration conditions (steps 1 and 2) shown below:
Hg(OAc)2, CH3OH
2 NaBH4
Expected product: Actual product: Note: (S)-3-vinylcyclopentanone has two strong IR peaks at 1748 cm-1 and 1642 cm-1. NMR Peaks: Î´ 2.5-3 ppm (2H), 5-6 ppm (3H), and Î´ 20 ppm (PC NMR peak).

(3 pts) In the first box provided above, draw the expected (stable) alkoxymercuration product if the complete alkoxymercuration reaction proceeds normally. The expected product would have a strong IR peak at 1748 cm-1 and a peak in the CNMR spectrum at Î´ 20 ppm. No IR peaks are observed in the 500-1700 cm range, nor are any peaks visible in the H NMR spectrum between 5-6 ppm. The expected product would also react with 2,4-dinitrophenylhydrazine to form a solid 2,4-dinitrophenylhydrazone derivative. If you are not 100% sure of your structure, explain what led you to choose your structure.

b. (3 pts) Instead of the expected alkoxymercuration product (first box), you actually isolated a different molecule at the end of this two-step complete alkoxymercuration. The actual product shows a strong, broad IR peak at 3400 cm-1 but has no IR peak at 1749 cm-1. It lacks downfield C (>100 ppm) and H NMR ppm) peaks. The actual product does not react with 2,4-dinitrophenylhydrazine, but will react with NaH (sodium hydride) to form a gas. Draw the actual product of this reaction in the second box provided above. If you are not 100% sure of your structure, explain what led you to choose your structure.

(2 pts) Explain why the actual product was formed instead of the expected product.

d. (2 pts) On the basis of your explanation for part c, suggest different reagents (you may have to invent a new reagent) or reaction conditions you might use to make the alkoxymercuration give the expected product instead of the actual product formed above.

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