Question

1. Write the mechanism for the reaction between bromobenzene and magnesium (ether solvent). 2. Write the mechanism for the reaction between the product from the reaction in question 1 and benzophenone. If this reaction is treated with water, what will the final product be? 3. Write the mechanism for the reaction between the product from the reaction in question 1 and carbon dioxide (CO2) followed by the addition of acid. Again, show the product. 4. What side products are likely to form during the synthesis in question 3? Hint: There are two major ones. ? Impurity 1 exhibits one peak in the 1H-NMR at 7.2 ppm. Its 13C-NMR has one signal at 128.5 ppm. ? Impurity 2 contains a multiplet of peaks between 7.4 and 7.6 ppm in the 1H-NMR. The 13C-NMR and IR spectra of this compound are attached to the end of this document. 5. Outline a separation scheme for isolating the product in question 3 from the reaction mixture. 6. Write a balanced equation for the reaction between the product in question 3 and sodium hydroxide. Why is the ether layer extracted with sodium hydroxide rather than water?

          1. Write the mechanism for the reaction between bromobenzene and magnesium
(ether solvent).
2. Write the mechanism for the reaction between the product from the reaction in
question 1 and benzophenone. If this reaction is treated with water, what will the
final product be?
3. Write the mechanism for the reaction between the product from the reaction in
question 1 and carbon dioxide (CO2) followed by the addition of acid. Again,
show the product.
4. What side products are likely to form during the synthesis in question 3? Hint:
There are two major ones.
? Impurity 1 exhibits one peak in the 1H-NMR at 7.2 ppm. Its 13C-NMR has
one signal at 128.5 ppm.
? Impurity 2 contains a multiplet of peaks between 7.4 and 7.6 ppm in the
1H-NMR. The 13C-NMR and IR spectra of this compound are attached to
the end of this document.
5. Outline a separation scheme for isolating the product in question 3 from the
reaction mixture.
6. Write a balanced equation for the reaction between the product in question 3 and
sodium hydroxide. Why is the ether layer extracted with sodium hydroxide rather
than water?

1. Write the mechanism for the reaction between bromobenzene and magnesium
(ether solvent).
2. Write the mechanism for the reaction between the product from the reaction in
question 1 and benzophenone. If this reaction is treated with water, what will the
final product be?
3. Write the mechanism for the reaction between the product from the reaction in
question 1 and carbon dioxide (CO2) followed by the addition of acid. Again,
show the product.
4. What side products are likely to form during the synthesis in question 3? Hint:
There are two major ones.
? Impurity 1 exhibits one peak in the 1H-NMR at 7.2 ppm. Its 13C-NMR has
one signal at 128.5 ppm.
? Impurity 2 contains a multiplet of peaks between 7.4 and 7.6 ppm in the
1H-NMR. The 13C-NMR and IR spectra of this compound are attached to
the end of this document.
5. Outline a separation scheme for isolating the product in question 3 from the
reaction mixture.
6. Write a balanced equation for the reaction between the product in question 3 and
sodium hydroxide. Why is the ether layer extracted with sodium hydroxide rather
than water?

Added by Allison C.

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