1a: Write the overall reaction for our esterification reaction, and its mechanism. 1b: Using the “rule of six”, predict the solubilities in water of benzoic acid, methanol, and methyl benzoate. 1c: If the 4.0 g of benzoic acid used in this reaction is limiting, what mass of methyl benzoate is predicted to be formed if you achieve 100% yield? Show your calculation

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
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1a: Write the overall reaction for our esterification reaction, and its mechanism.
1b: Using the “rule of six”, predict the solubilities in water of benzoic acid, methanol, and
methyl benzoate.
1c: If the 4.0 g of benzoic acid used in this reaction is limiting, what mass of methyl benzoate
is predicted to be formed if you achieve 100% yield? Show your calculation

Procedure
Set up a ring stand near a water faucet with two clamps (the two prong type works best) and a
heating mantle. The heating mantle should be screwed onto the ring stand at the base. Next,
clamp a reflux condenser into the clamps and attach it to the ring stand above the heating mantle.
Attach reflux tubing to the water inlet and outlet nozzles with water flowing in through the
1 of 2
bottom and out through the top. Begin the water flow through the condenser slowly. Add a small
amount of Vaseline to the bottom of the reflux condenser's ground glass joint to prevent seizing.
Add 4 g of benzoic acid to a 50 mL round bottom flask with 19/22 joints from your Chem Kit.
To the flask, add 4 mL of methanol along with a boiling chip. Next, slowly add 1 mL of
concentrated sulfuric acid to the 50 mL round bottom flask containing the benzoic acid and the
methanol. Place the penny head stopper in the neck of the flask and return to your bench.
Remove the stopper from the 50 mL round bottom flask and attach it to the bottom of the reflux
condenser. Lower the reflux apparatus into the heating mantle and set the heating mantle to 6.
Heat the mixture for half an hour, watching carefully to prevent the mixture from boiling too
vigorously as this will cause the loss of the alcohol through the top of the condenser.
Transcribed Image Text:Procedure Set up a ring stand near a water faucet with two clamps (the two prong type works best) and a heating mantle. The heating mantle should be screwed onto the ring stand at the base. Next, clamp a reflux condenser into the clamps and attach it to the ring stand above the heating mantle. Attach reflux tubing to the water inlet and outlet nozzles with water flowing in through the 1 of 2 bottom and out through the top. Begin the water flow through the condenser slowly. Add a small amount of Vaseline to the bottom of the reflux condenser's ground glass joint to prevent seizing. Add 4 g of benzoic acid to a 50 mL round bottom flask with 19/22 joints from your Chem Kit. To the flask, add 4 mL of methanol along with a boiling chip. Next, slowly add 1 mL of concentrated sulfuric acid to the 50 mL round bottom flask containing the benzoic acid and the methanol. Place the penny head stopper in the neck of the flask and return to your bench. Remove the stopper from the 50 mL round bottom flask and attach it to the bottom of the reflux condenser. Lower the reflux apparatus into the heating mantle and set the heating mantle to 6. Heat the mixture for half an hour, watching carefully to prevent the mixture from boiling too vigorously as this will cause the loss of the alcohol through the top of the condenser.
Remove the stopper from the 50 mL round bottom flask and attach it to the bottom of the reflux
condenser. Lower the reflux apparatus into the heating mantle and set the heating mantle to 6.
Heat the mixture for half an hour, watching carefully to prevent the mixture from boiling too
vigorously as this will cause the loss of the alcohol through the top of the condenser.
After the reaction has refluxed for one hour, turn off the heating mantle and allow the reaction
mixture to cool. Retrieve the 125 mL separatory funnel from your Chem Kit. Obtain a ring for
your ring stand and screw it into place allowing enough room to accommodate the separatory
funnel with a 150 mL beaker beneath it. Add the cooled contents of the 50 mL round bottom
flask to the separatory funnel using a Pasteur pipet. Obtain 20 mL of 10% sodium bicarbonate
solution. Slowly add the 10% sodium bicarbonate solution to the separatory funnel using a
Pasteur pipet. Gently swirl the separatory funnel without the stopper until the bubbling begins to
slow. Stopper the funnel and invert several times with frequent venting to prevent pressure build
up. Allow the layers to separate and then add 20 mL of saturated sodium chloride solution to the
separatory funnel. Repeat the inverting and venting procedure. Slowly drain the bottom layer
into a waste beaker and set it aside. Add another 20mL of the saturated sodium chloride solution
to the separatory funnel stopper and invert several times. Allow the layers to separate and slowly
drain the bottom layer into the waste beaker. Let the top layer stand in the separatory funnel.
Set up a distillation apparatus as demonstrated at the front of the lab using the 50 mL round
bottom flask as the boiling flask and a 25 mL round bottom flask as the collection flask. Use
caution when inserting the thermometer into the thermometer adapter. Add the remaining liquid
in the separatory funnel to the distillation flask, turn on the water to the condenser and set the
heating mantle to 9. Small quantities of water may still be present but this will not affect the
outcome of your experiment. Boil the contents until product (methyl benzoate) begins to drip
into the collection flask. When half of the contents have distilled into the collection flask, read
the temperature on the thermometer this is the boiling point of methyl benzoate. Distill as much
of the liquid from the distillation flask as possible without scorching the contents. Place your
ester into a labeled vial and wait for further instruction.
Allow your distillation apparatus to cool before disassembling. Rinse the contents of the
distillation flask out with water and acetone and then wash with hot soapy water rinsing with
DI water when finished.
We will analyze by IR spectroscopy. Using the web resource, retrieve the IR spectrum for
methyl benzoate, and have it ready to compare with your experimental spectrum.
Transcribed Image Text:Remove the stopper from the 50 mL round bottom flask and attach it to the bottom of the reflux condenser. Lower the reflux apparatus into the heating mantle and set the heating mantle to 6. Heat the mixture for half an hour, watching carefully to prevent the mixture from boiling too vigorously as this will cause the loss of the alcohol through the top of the condenser. After the reaction has refluxed for one hour, turn off the heating mantle and allow the reaction mixture to cool. Retrieve the 125 mL separatory funnel from your Chem Kit. Obtain a ring for your ring stand and screw it into place allowing enough room to accommodate the separatory funnel with a 150 mL beaker beneath it. Add the cooled contents of the 50 mL round bottom flask to the separatory funnel using a Pasteur pipet. Obtain 20 mL of 10% sodium bicarbonate solution. Slowly add the 10% sodium bicarbonate solution to the separatory funnel using a Pasteur pipet. Gently swirl the separatory funnel without the stopper until the bubbling begins to slow. Stopper the funnel and invert several times with frequent venting to prevent pressure build up. Allow the layers to separate and then add 20 mL of saturated sodium chloride solution to the separatory funnel. Repeat the inverting and venting procedure. Slowly drain the bottom layer into a waste beaker and set it aside. Add another 20mL of the saturated sodium chloride solution to the separatory funnel stopper and invert several times. Allow the layers to separate and slowly drain the bottom layer into the waste beaker. Let the top layer stand in the separatory funnel. Set up a distillation apparatus as demonstrated at the front of the lab using the 50 mL round bottom flask as the boiling flask and a 25 mL round bottom flask as the collection flask. Use caution when inserting the thermometer into the thermometer adapter. Add the remaining liquid in the separatory funnel to the distillation flask, turn on the water to the condenser and set the heating mantle to 9. Small quantities of water may still be present but this will not affect the outcome of your experiment. Boil the contents until product (methyl benzoate) begins to drip into the collection flask. When half of the contents have distilled into the collection flask, read the temperature on the thermometer this is the boiling point of methyl benzoate. Distill as much of the liquid from the distillation flask as possible without scorching the contents. Place your ester into a labeled vial and wait for further instruction. Allow your distillation apparatus to cool before disassembling. Rinse the contents of the distillation flask out with water and acetone and then wash with hot soapy water rinsing with DI water when finished. We will analyze by IR spectroscopy. Using the web resource, retrieve the IR spectrum for methyl benzoate, and have it ready to compare with your experimental spectrum.
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