Lab 3 Dehydration of Cyclohexanol
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Dec 6, 2023
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Chemistry 130: Synthesis of Cyclohexene and Tests for Unsaturation
1
Experiment 3
1
General
Principles
SYNTHESIS OF CYCLOHEXENE AND TESTS FOR
UNSATURATION
One general synthetic method used to prepare alkenes involves
dehydration
(elimination of water) of an alcohol.
A strong and high-boiling mineral acid, such as sulfuric or phosphoric acid, is
the catalyst for the reaction. The acid protonates the alcohol (step 1, below).
Subsequently, a molecule of water is eliminated to form a carbocation and
water (step 2). A proton (H
+
) is then eliminated from the carbocation to make
the alkene (step 3). The elimination (
E1 mechanism
) proceeds step-wise
through a highly reactive
carbocation
intermediate.
If the two carbons adjacent to the alcohol are attached to different atoms, it is
possible to obtain two or more different alkenes. In the experiment you will
perform, this complication is avoided by using a symmetrically substituted
alcohol.
Notice that since every step in this reaction is reversible, hence the overall
reaction is reversible. Reversibility is indicated by the half-arrows pointing to
the right and left. Reversible reactions can reach a state of dynamic equilibrium,
where the rate of the forward reaction is equal to the rate of the reverse
reaction, preventing further formation of product. Since this reaction is
reversible, we will have to apply Le Châtelier’s Principle to drive the reaction to
the desired alkene. An understanding of equilibrium is essential for many
systems. The interactions of hormones with receptors, drug absorption,
electrolyte balance, and many other processes are guided by equilibrium
principles.
C
C
OH
H
H
+
heat
C
C
H OH
+
Alcohol
Alkene
C
C
O
H
H
+
H
C
C
O
+
H
H
H
C
C
H
+ H
2
O
C
C
H
C
C
+ H
+
step 1
step 2
step 3
+
carbocation
Experiment 3
2
2
Cyclohexene
from
Cyclohexanol
CAUTION
Corrosive liquid
CAUTION
Flammable
NOTE
Add boiling stones
CAUTION
DO NOT distill to
dryness
In this experiment the secondary alcohol cyclohexanol will be dehydrated
to cyclohexene (you will determine its structure in a prelab exercise):
Experimentally, advantage is taken of the fact that alkenes boil at much
lower temperatures than the alcohols from which they are prepared. The
alcohol is heated (with acid) to a temperature above the boiling point of
the alkene but below that of the alcohol. The alkene and water distill from
the reaction flask as they are formed, whereas the unchanged alcohol
remains behind to be further acted on by the acid. In the present case,
the dehydration is carried out at 130-140
°
C, which is above the boiling
point of cyclohexene (83
°
C) but below that of cyclohexanol (161
°
C).
Phosphoric acid is a corrosive liquid. Avoid contact of this acid with
your skin or clothing. Wear gloves. If you have an accidental spill,
wash immediately with a large amount of water.
Cyclohexanol and cyclohexene are flammable. Be sure that your
distillation apparatus is put together snugly. Be sure that organic
vapors and liquid do not come near the heat source.
Procedure:
Write all observations in your lab notebook!
1. Arrange a simple distillation apparatus as shown in Figure 4.1.
2. Add 16 g (16.7 mL, 0.16 mol) of cyclohexanol (specific gravity = 0.96)
and 10 mL of concentrated phosphoric acid to a 50-mL round-bottomed
flask.
3. Mix the contents thoroughly by swirling before connecting the flask to
the distillation setup.
4. Add two boiling stones, and heat the flask gently so that the
temperature of the distilling vapor does not exceed 100
°
C.
Have the TA check your setup before turning on the heat!
5. Continue the distillation until only a few milliliters of high-boiling residue
remain in the flask.
Complete the observations and reflections on the report sheet
before proceeding. You should be able to work on this as your
reaction proceeds.
!
!
!
!
H
+
heat
cyclohexanol
OH
Chemistry 130: Synthesis of Cyclohexene and Tests for Unsaturation
3
1
Complete the observations as you perform the “workup” steps.
6. Transfer the distillate to a small separatory funnel and add 4 mL of saturated sodium chloride
solution.
7.
Observe
which layer gets larger upon addition of sodium chloride. Does it dissolve in the top
layer or the bottom layer? Use this information to determine if the aqueous layer is on the top or
bottom.
8. Then slowly add 4 mL of 10% sodium carbonate solution to neutralize any traces of acid. Swirl
or shake the mixture gently.
Observe
what happened as the sodium carbonate is added. Why
are we adding sodium carbonate? (Pressure will build if you shake too rigorously, blowing off the
cap of the sep funnel.)
9. Allow the layers to separate, and then draw off the aqueous layer. Set it aside in case you
accidentally took the wrong layer.
10. Pour the crude cyclohexene out of the separatory funnel into a small, dry 50-mL Erlenmeyer
flask. Write
observations
in your notebook. Is the solution clear, cloudy, colorless, etc.?
11. Add ~0.5 g of anhydrous sodium sulfate granules to the cyclohexene (it should not dissolve!)
and allow it to stand for 10-15 minutes, swirling it occasionally. The sodium sulfate is used to
remove traces of water from, the cyclohexene.
Observe
what happens to the solution. The
product should be clear, not cloudy.
12. Carefully decant your product into a dry beaker of known mass. Weigh the product and
calculate the percent yield.
Experiment 3
4
3
Tests for
Unsaturation
Bromine decolorization is used as a simple qualitative test for unsaturation.
Thus a dilute solution of bromine is some inert colorless solvent, such as
dichloromethane, is rapidly decolorized when it is added to an alkene or alkyne.
In contrast, most saturated compounds do not decolorize bromine solutions.
CAUTION
Toxic
In this part of the experiment you will apply this test to the cyclohexene you
prepared, in order to demonstrate that it does contain a carbon-carbon double
bond. For comparison, you will also test the structurally similar but saturated
hydrocarbon cyclohexane.
Bromine is toxic and can cause skin burns. Avoid skin contact with the
bromine solution and do not breathe its vapors. Wear gloves and work in
a hood.
Procedure for the Bromine Test
1.
Dissolve 5 drops of the cyclohexene you prepared in 1 mL of dichloromethane in a test tube.
Observe (and record)
the color of the solution.
2.
Observe
(and record)
the color of a solution of 5% bromine in dichloromethane.
3.
Add the bromine solution dropwise from a buret
(under the hood)
while shaking the test tube.
4.
Observe (and record)
the color of the resultant solution. Continue adding the bromine solution
until the bromine color is no longer lost (i.e. until the solution begins to retain the color of bromine).
5.
Record
the volume of bromine solution that was added.
6.
For comparison, repeat the test (steps 1-5) using
cyclohexane
in place of cyclohexene.
Complete the reflections on the report sheet before leaving lab.
Waste Disposal
Empty the contents of the test tubes into a waste bottle for halogenated organic solvents.
C
C
C
C
+
Br
2
Br
Br
!
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