Joy Osuofa

CHEM 3210
Section 302
06/24/15
Cyclohexanol Dehydration
Summary:
In this experiment, we are going to be looking at acid catalyzed
dehydration of alcohols. This dehydration process of cyclohexanol to
cyclohexene can be done by pyrolysis of the cyclic secondary alcohol
with an acid catalyst at a modest temperature or distillation over
alumina or silica gel. The procedure for this experiment involves
catalysis by phosphoric acid. When a mixture of cyclohexanol and
phosphoric acid is made, it produces water. The mechanism of this this
reaction involves initial rapid protonation of the hydroxyl group and
phosphoric acid. This is followed by loss of water to give the unstable
secondary carbocation, which loses a proton to water to give the
alkene.
Chemical

Molar Mass

Density

Cyclohexan
ol
Phosphoric
Acid
Toluene

100.158
g/mol
98 g/mol

962.00
kg/m
1.88 g/cm

92.14
g/mol
110.98
g/mol
58.44
g/mol

866.90
110.6C
kg/m
2.15 g/cm3 1935C

-95C

2.16 g/cm

801C

Calcium
Chloride
Sodium
Chloride

Boiling
Point
160.8C

Melting
Point
25.9C

158C

42.35C

1413C

772C

Experimental Procedure:
1. Add 2g of cyclohexanol followed by 0.5mL of 85% phosphoric
acid and a boiling chip into a 5-mL round-bottomed, long-necked
flask.
2. Add a copper sponge to the neck of the flask and shake to mix
layers
3. Heat the mixture gently on a sand bath then distill until the
residue in flask has a volume of about 0.5 mL to 1.0 mL, and
little distillate is formed. Record the temperature range.
4. Allowed assembly to cool once removed from sand, and briefly
remove the thermometer. Next, add 2 mL of toluene into the top
of the column using a pipette.
5. Notice the amount of the upper layer in the boiling flask and
distill again until half has reduced volume of the layer.

Joy Osuofa
CHEM 3210
Section 302
06/24/15
6. Transfer contents of the vial into a reaction tube and rinse out
the vial with a small amount of toluene.
7. Wash the mixture with an equal volume of saturated sodium
chloride, remove the aqueous layer and then add a good amount
of calcium chloride to reaction tube.
8. Let the solution dry for at least 5 minutes while shaking it with
the drying agent.
9. Clean the distilling apparatus, with water, then ethanol, and then
some acetone.
10.
Make sure the apparatus is completely dry, otherwise the
product can become contaminated.
11.
Before you start the distillation process, noted the
barometric pressure and determine pressure and determine
reading.
12.
Transfer the dry cyclohexane solution to distilling flask, add
a boiling chip and distill product.
13.
Stop the distillation when the temperature rises above the
peak of the products distillation.
14.
Record yield in grams and percent.
15.
Run (IR) spectrum and interpret it for purity.
16.
Clean up area.
Pre-Lab Questions
1. Which products would be obtained by the dehydration of 2heptanol? Of 2-methyl-1-cyclohexanol?
- We would get 1-heptane and 2-heptane for 2 heptanol; And for 2 methyl-1cyclohexanol, we would get 1-methylcyclehexene and 3-methylcyclohexene.