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O
CH3CH2OH
CH3C Cl
OH
O- H+ + H+
CH3C Cl
CH3C Cl
Step
2
O
O+
CH
CH
3
2
CH3CH2 H
Step1
Step 3
O
HCl
CH3CH2OCCH3
O
Step 4
CH3C
O
CH3CH2
H
+
Cl-
Aspirin can be produced in a one step chemical process by reacting salicylic acid
with acetyl chloride, according to the reaction
Aspirin is a white solid that is almost completely insoluble in water. We will use this
physical property of our product to separate it from the final solution.
Thin layer chromatography (TLC) is used to separate and identify aspirin. Small
amounts of the synthesized product, starting material (salicylic acid) and
commercial aspirin are placed along one edge of a chromatography plate. The plate
is then placed in a container with solvent. With the plate acting like a wick, the
solvent flows up the chromatogram, carrying the samples with it. Molecules that are
more soluble in the solvent will move higher on the paper; the molecules that are
more attracted to the plate will remain closer to the original line. After removing
the plate, the samples can be detected wit UV light/iodine chamber.
Procedure:
1. Place 1.4 g (0.01 mol) of salicylic acid in a 20 mL test tube and add 1 mL of
pyridine (just sufficient to dissolve it) while the tube rests in an ice bath. Keep the
test tube in the fume hood!
2. Point the open end of the test tube away from you and your partners.
Occasionally the reaction goes quickly and shoots material out of the tube! Add 1
mL of acetyl chloride to the tube. Keep the mixture in the fume hood!
3. The mixture becomes viscous at this stage. Place tube in the ice bath for 15 min.
( it does not need to be in the hood).
4. While waiting, set up a vacuum filter flask with a Bchner funnel and a piece of
filter paper which just fits the bottom of the funnel, as shown in Figure 2 below.
Attach a thick rubber tube to an aspirator mounted on a water faucet.
5. Add 5 mL of cold water to the test tube and cap it with a rubber stopper. Shake
the mixture. Do this cautiously at first until you are sure that no violent reaction is
occurring. The mixture should turn cloudy. Shaking is continued until a white
product appears (it may take several minutes, be patient!)
6. Turn on the water faucet all the way and check to be sure you have good suction.
Break the suction by disconnecting the tube from the flask (leave the water
running). Pour the mixture into the funnel, trying to get as much of the solid
transferred as possible. Connect the hose and apply full suction for at least 30
seconds. Wash the crystals with cold water. Break the suction. Do not just turn off
the water; this may create a back-flow of the water into your filter flask. Dry them
on the filter paper for about 1 hr.
Part B- Recrystallization
1. Carefully scrape off 1/10 of your crystals into a 50 mL beaker. Add about 3 mL of
cold water and place the mixture on a hot plate in a hood. Heat until all of the
crystals dissolve. When the crystals are completely dissolved, remove the beaker
and allow it to cool. You should see nice crystals of aspirin beginning to form! When
the recrystallization is complete, filter again, and dry.
Part C- Melting Point:
1. Measure the melting point with melting point apparatus
Calculations:
Calculate the theoretical yield of aspirin in grams.
Yield =
Calculate the actual yield of aspirin in grams by weighing the product.
Use this to calculate the % yield for this experiment.
Result: Report the yield and % yield, Melting point range of your aspirin and
Chemical literature melting point
Reaction and mechanism of aspirin synthesis with acetic anhydride and
sulphuric acid