Introduction: This lab will further familiarize students with laboratory techniques,

particularly so those that are utilized in dehydration since students will be dealing with
the alcohol dehydration of 2-methylcyclohexanol. Such processes are meant to aid in the
development of thorough comprehension of reaction mechanisms as oft learned in
introduction organic chemistry classes.This process will portray for students the Zaitsev
rule in action. This particular experiment will see the development from concentrated
sulfuric acid/phosphoric acid to the mix of 1-methylcyclohezene and 3methylcyclohexene. In order to understand the products within the mixture, students will
further delve into their organic laboratory skills as they will choose from the
implementation of gas chromatography or refractive index measure. From these
aforementioned techniques, there will be an understanding of the relationship of molar
concentration and refractive index.
Experimental Procedure
I.
Combine 10 g of 2-methylcyclohexanol with 2.5 ml 85% phosphoric acid in a
small distilling flask
a. The flask should have a thermometer, fractionating column, and water
cooled condenser
b. Mix
II.
Heat the flask so that the distillate does not exceed 95 degrees Celsius
a. Otherwise, too much unreacted alcohol would distillate
III.
Heat until distillation extremely slows down and collection of 10ml product has
occurred
IV. Using a separatory funnel and water, wash the distillate
a. Follow through with 10% sodium bicarbonate
b. Add water again
V. Dry organic compound over anhydrous calcium chloride
a. Filter
b. Analyze with gas chromatography
Table of Reagents
Compound
2methylcyclohexano
l

M.W

M.P. B.P

114.18546 -9.5
C

165-155
DEGREE
SC

Refractiv
e index

Density Solubilit
y
0.93
-Not very
soluble in
water

Safety
Hazards
-flammable
-explosive
above 58 c
-Exposure to
skin may
result in
redness
-Inhalation
may result in
a cough and
headache
-Eye

exposure
results in
redness
Phosphoric acid

97.995182 42.4
c

407 c

Sodium bicarbonate 84.006609 50 c

Anhydrous calcium
chloride

110.984

775
c

1935 c

1.34203

1.8741

1.5

2.20

1.4420

2.15

-Soluble
in water
and
alcohol
-Soluble
with
ethanol

-Skin
exposure
may result in
redness,
pain, burns,
and blisters
-Inhalation
may result in
burning
feeling,
cough,
shortness of
breath, and
sore throat
-Eye
exposure
may result in
pain,
redness, and
severe burns
-ingestion
may result in
abdominal
pain,
burning
feeling and
shock
-Not
-Eye
soluble in exposure
ethanol
may result in
-Soluble redness
in water
-Soluble -Skin
with
exposure
methyl
may result in
carbonate redness, dry
and
skin, and
acetic
burns
acid
-Inhalation
-Soluble may result in
with
cough, sore
ethanol
throat, and

-Soluble
with
water

burning
feeling
-Eye
exposure
may result in
redness, pain
and burns
-Ingestion
may result in
mouth and
throat burns,
nausea, and
vomiting