Question

For the nitration of methyl benzoate:

a. Which product did you get? What evidence do you have for this?

b. Was your product pure? What evidence do you have for this? Explain your evidence.

c. Draw the mechanism for the product you got.

For the bromination of acetanilide:

a. Which product did you get? What evidence do you have for this?

b. Was your product pure? What evidence do you have for this? Explain your evidence.

c. Draw the mechanism for the product you got.
Nitration of Methyl Benzoate Add approximately 0.3 ml concentrated sulfuric acid to approximately 0.3 ml concentrated nitric acid in a small dry conical vial. (Dry your glass ware in a drying oven if you must wash it before use. A trace amount of "dirt" will do less damage than any water!) Cap the vial and chill it in an ice bath. While the nitrating mixture cools, add approximately 0.42 mL methyl benzoate to a dry 10-mL round-bottom flask. Make sure to record the exact mass of methyl benzoate used, as you will need that value for theoretical yield determination. Place the flask with the methyl benzoate in an ice water bath and allow it to cool to -0°C. Add a small stir bar to this flask and slowly add approximately 0.9 ml concentrated sulfuric acid. Be sure not to allow the temperature of this mixture to exceed 5°C. With the two starting materials ready to go, use a pipette to slowly add about half of the nitrating mixture to the flask containing the methyl benzoate. Try to keep the temperature as close to 0°C as possible. Any water present in this reaction (from your ice bath or wet glass ware) and a too high reaction temperature will reduce your yield significantly. After a couple minutes, slowly add the remainder of the nitrating mixture. After complete addition of the nitrating mixture, allow the reaction to stir in the ice bath for 10- 15 minutes. After this time, remove the reaction flask from the ice water bath and allow it to warm to room temperature. Transfer the reaction mixture into a 25-ml Erlenmeyer flask that contains a handful of crushed ice. Swirl the mixture occasionally and allow it to warm to room temperature. Collect the solid product by using vacuum filtration with the Hirsch funnel. Wash the solid product with two 1-ml portions of cold water. Transfer all of the waste generated in this experiment so far, to the waste bottle reserved for strong acid waste (sulfuric acid and nitric acid). Do NOT add methanol to the waste bottle reserved for strong acid waste.

Answer 1

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Date Page BTOmination 4 acetanilide ИN H N Ace tic acid P-bromaacea Brominatim acetanilide takes place at Position be cause para activating group is presen Pure high yield is auso electron donating saupHCOC to ring Incoming electophile is para &ortho Product obtainad is oPpaineld be cause is atached para positon becawe elecpon aich come at pasiHans Mechanism:l сha 8T2 и BT Depratoration NK- Chз BO It is bromination reac Hon brominaitn in caf. acetanillde occure maferly au be cause atho pas1kim has hindered p0 sIrion due to -N-COC gooup para position