Calculate the molarity of the solution of sodium hydroxide that is used. a. M = b. If the original procedure is the base scale (100%), how far are we scaling down the reaction when using 0.75 mL of methyl salicylate? (Example: the original uses 2.0 mL, if we were to use 1.0 mL, we would be scaling the reaction down to 50% compared to the original) c. If we use 0.75 mL of methyl salicylate instead, how much of the water would we need instead? d. About how much water might we expect to use for the recrystallization of the salicylic acid formed from the hydrolysis of 0.75 mL of methyl salicylate? (use p36 and your answer to #d). e. About how much 3M sulfuric acid will you need to neutralize the salt that forms?

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Here is an example of a formal procedure based off of the experiment presented in Mohrig:
Sodium hydroxide (4.6 g) was dissolved in water (25 mL). This solution was added to a 100
mL round bottom flask along with methyl salicylate (2.0 mL) and a stir bar. The mixture was
heated at reflux for 15 min and then progressively cooled to 5 °C. The solution was acidified
with 3M sulfuric acid (15-20 mL), and the resulting solid was collected by vacuum filtration.
The crude salicylic acid was recrystallized from water to yield ???? g of final solid. The melting
point and IR were taken to assess purity.

Calculate the molarity of the solution of sodium hydroxide that is used.
a. M =
b. If the original procedure is the base scale (100%), how far are we scaling down the
reaction when using 0.75 mL of methyl salicylate? (Example: the original uses 2.0 mL, if
we were to use 1.0 mL, we would be scaling the reaction down to 50% compared to the
original)
c. If we use 0.75 mL of methyl salicylate instead, how much of the water would we need
instead?
d. About how much water might we expect to use for the recrystallization of the salicylic acid
formed from the hydrolysis of 0.75 mL of methyl salicylate? (use p36 and your answer to
#d).
e. About how much 3M sulfuric acid will you need to neutralize the salt that forms?
36
Part 1 Exp eriments
2.0 mL (2.3 g, 0.015 mol) of methyl salicylate. A white solid will
ALWAYS grease ground glass quickly form (see Question 3). Attach a water-cooled reflux con-
joints [see Technique 2.1].
denser to the round-bottomed flask [see Technique 3.3].
Add one or two boiling stones to the reaction mixture to pre-
vent bumping of the solution when it is heated and place a heat-
ing mantle under the flask [see Technique 3.2]. Heat the reaction
mixture at boiling for 15 min. The solid that forms initially will
dissolve as the mixture is warmed.
After the reflux period, remove the heating mantle and let the
mixture cool to room temperature. Placing a beaker of tap water
under the flask speeds the cooling process.
Carefully add 3 M sulfuric acid solution in approximately
3-mL increments until a heavy white precipitate of salicylic acid
forms and remains when the mixture is well stirred. You will need
approximately 15-20 mL of the sulfuric acid solution.
After you have added just enough 3 M sulfuric acid to give a
heavy white precipitate, add 2 mL more acid to ensure complete
precipitation of the salicylic acid. Cool the mixture in an ice-water
bath to about 5°C. Collect the precipitated crude product by vac-
uum filtration, using a Buchner funnel [see Technique 5, Figure
5.4].
Recrystallization of Recrystallize the crude salicylic acid by the following procedure.
Salicylic Acid
Heat about 60 mL of water in a 125-mL Erlenmeyer flask on a hot
plate until the water almost boils. Place the crude salicylic acid in
Read Technique 5,
Recrystallization, carefully
before doing this part of the
еxperiment.
another 125-mL Erlenmeyer flask and add a boiling stone or
wooden boiling stick. Carefully pour approximately 20 mL of hot
water over the salicylic acid and heat the flask containing the sali-
cylic acid to boiling.
SAFETY PRECAUTION
Use a pair of flask tongs to hold any hot flask.
Continue adding approximately 5-mL portions of hot water
until the solid has completely dissolved, allowing a little time after
each addition for the dissolution process to occur. When dissolu-
Transcribed Image Text:36 Part 1 Exp eriments 2.0 mL (2.3 g, 0.015 mol) of methyl salicylate. A white solid will ALWAYS grease ground glass quickly form (see Question 3). Attach a water-cooled reflux con- joints [see Technique 2.1]. denser to the round-bottomed flask [see Technique 3.3]. Add one or two boiling stones to the reaction mixture to pre- vent bumping of the solution when it is heated and place a heat- ing mantle under the flask [see Technique 3.2]. Heat the reaction mixture at boiling for 15 min. The solid that forms initially will dissolve as the mixture is warmed. After the reflux period, remove the heating mantle and let the mixture cool to room temperature. Placing a beaker of tap water under the flask speeds the cooling process. Carefully add 3 M sulfuric acid solution in approximately 3-mL increments until a heavy white precipitate of salicylic acid forms and remains when the mixture is well stirred. You will need approximately 15-20 mL of the sulfuric acid solution. After you have added just enough 3 M sulfuric acid to give a heavy white precipitate, add 2 mL more acid to ensure complete precipitation of the salicylic acid. Cool the mixture in an ice-water bath to about 5°C. Collect the precipitated crude product by vac- uum filtration, using a Buchner funnel [see Technique 5, Figure 5.4]. Recrystallization of Recrystallize the crude salicylic acid by the following procedure. Salicylic Acid Heat about 60 mL of water in a 125-mL Erlenmeyer flask on a hot plate until the water almost boils. Place the crude salicylic acid in Read Technique 5, Recrystallization, carefully before doing this part of the еxperiment. another 125-mL Erlenmeyer flask and add a boiling stone or wooden boiling stick. Carefully pour approximately 20 mL of hot water over the salicylic acid and heat the flask containing the sali- cylic acid to boiling. SAFETY PRECAUTION Use a pair of flask tongs to hold any hot flask. Continue adding approximately 5-mL portions of hot water until the solid has completely dissolved, allowing a little time after each addition for the dissolution process to occur. When dissolu-
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