18) In one of your experiments, you used a Grignard reaction to make a carboxylic acid. Br 1) Mg 2) CO2 As part of this experiment, the following procedures were given: 1. When the Grignard reaction begins to slow down, place 10 g of crushed dry ice in a 150 mL beaker. Do not take time to weigh the dry ice. Use approximately the amount in the beaker indicated by your instructor. The CO2 is in large excess and will not affect your calculation of percent yield of benzoic acid product. Cover the beaker with a watch glass. 2. When most of the magnesium has reacted and the ether boiling subsides, quickly pour the contents of the tube into the beaker containing dry ice. 3. Add a few milliliters of ether to the test tube and swirl to rinse. Add the rinse liquid to the beaker. 4. Cover the beaker with the watch glass and allow it to stand until the next lab period. During the interim, the excess dry ice will have sublimed. 5. Hydrolyze the Grignard addition product by slowing adding 30 mL of 6M HCl to the beaker with the sublimed dry ice and reaction mixture. Stir the mixture with a glass stirring rod. If there is excess magnesium present, it will react with the HCl to evolve hydrogen gas. 6. Add 30 mL of tert-butyl methyl ether (TBME) to the beaker. Stir the mixture. There should now be two distinct liquid layers. a) What is the structure of the organic compound present in the beaker at the end of step 4? b) What happens when the 6M HCI is added in step 5? (give a mechanism) c) Use a flowchart to show what happens during step 6 above.

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18) In one of your experiments, you used a Grignard reaction to make a carboxylic acid.
„Br 1) Mg
2) CO2
As part of this experiment, the following procedures were given:
1. When the Grignard reaction begins to slow down, place 10 g of crushed dry ice in a 150 mL
beaker. Do not take time to weigh the dry ice. Use approximately the amount in the beaker indicated
by your instructor. The CO2 is in large excess and will not affect your calculation of percent yield of
benzoic acid product. Cover the beaker with a watch glass.
2. When most of the magnesium has reacted and the ether boiling subsides, quickly pour the
contents of the tube into the beaker containing dry ice.
3. Add a few milliliters of ether to the test tube and swirl to rinse. Add the rinse liquid to the
beaker.
4. Cover the beaker with the watch glass and allow it to stand until the next lab period. During the
interim, the excess dry ice will have sublimed.
5. Hydrolyze the Grignard addition product by slowing adding 30 mL of 6M HCI to the beaker with
the sublimed dry ice and reaction mixture. Stir the mixture with a glass stirring rod. If there is excess
magnesium present, it will react with the HCl to evolve hydrogen gas.
6. Add 30 mL of tert-butyl methyl ether (TBME) to the beaker. Stir the mixture. There should now
be two distinct liquid layers.
a) What is the structure of the organic compound present in the beaker at the end of
step 4?
b) What happens when the 6M HCI is added in step 5? (give a mechanism)
c) Use a flowchart to show what happens during step 6 above.
Transcribed Image Text:18) In one of your experiments, you used a Grignard reaction to make a carboxylic acid. „Br 1) Mg 2) CO2 As part of this experiment, the following procedures were given: 1. When the Grignard reaction begins to slow down, place 10 g of crushed dry ice in a 150 mL beaker. Do not take time to weigh the dry ice. Use approximately the amount in the beaker indicated by your instructor. The CO2 is in large excess and will not affect your calculation of percent yield of benzoic acid product. Cover the beaker with a watch glass. 2. When most of the magnesium has reacted and the ether boiling subsides, quickly pour the contents of the tube into the beaker containing dry ice. 3. Add a few milliliters of ether to the test tube and swirl to rinse. Add the rinse liquid to the beaker. 4. Cover the beaker with the watch glass and allow it to stand until the next lab period. During the interim, the excess dry ice will have sublimed. 5. Hydrolyze the Grignard addition product by slowing adding 30 mL of 6M HCI to the beaker with the sublimed dry ice and reaction mixture. Stir the mixture with a glass stirring rod. If there is excess magnesium present, it will react with the HCl to evolve hydrogen gas. 6. Add 30 mL of tert-butyl methyl ether (TBME) to the beaker. Stir the mixture. There should now be two distinct liquid layers. a) What is the structure of the organic compound present in the beaker at the end of step 4? b) What happens when the 6M HCI is added in step 5? (give a mechanism) c) Use a flowchart to show what happens during step 6 above.
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