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Dehydration of Cyclohexane

Cyclohexanol was dehydrated using phosphoric acid to form cyclohexene, following Zaitsev's rule that the more substituted alkene is favored. Cyclohexanol and phosphoric acid were stirred and distilled to remove water. The distillate was extracted with brine and dried with sodium sulfate before final simple distillation. Simple distillation was important as a final step to remove any remaining cyclohexanol. Analysis using TLC and IR spectroscopy was used to identify the cyclohexene product and calculate percent yield.

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437 views4 pages

Dehydration of Cyclohexane

Cyclohexanol was dehydrated using phosphoric acid to form cyclohexene, following Zaitsev's rule that the more substituted alkene is favored. Cyclohexanol and phosphoric acid were stirred and distilled to remove water. The distillate was extracted with brine and dried with sodium sulfate before final simple distillation. Simple distillation was important as a final step to remove any remaining cyclohexanol. Analysis using TLC and IR spectroscopy was used to identify the cyclohexene product and calculate percent yield.

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Denine1997
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Names:

Course:

CHE 254L A

Professor: Dr.

The Dehydration of Cyclohexanol

Graphical Abstract:

Cyclohexanol
MW: 100.16
Density: 0.96 g/mL
mp: 25 oC bp: 161 oC

Cyclohexene
MW: 82.14
Density: 0.81 g/mL
mp: -103.7 oC

bp: 83.3 oC

Introduction:
Alcohols can be dehydrated by using an acid such as sulfuric or
phosphoric acid. The reaction removes water from the molecule and a C=C
double bond should form. The Russian chemist Zaitsev predicted that for a
dehydration reaction following the E1 mechanism, the more substituted C=C
is favored in the product. In this experiment with Cyclohexanol, Cyclohexene
should be formed as the major product. Using simple and fractional
distillation, along with Phosphoric Acid, this experiments purpose was to
prove whether Zaitsevs rule is true.

Figure 1: The Mechanism for the dehydration of Cyclohexanol to Cyclohexene


using Phosphoric Acid

Procedure:

A mixture of cyclohexanol (20.313 g) and concentrated H 3PO4 (10 mL) was


stirred in a 25 mL round-bottomed flask. Two boiling chips were added to the flask
and assembled onto a fractional distillation apparatus. The mixture was distilled
without completely drying out the round-bottomed flask. Distillate was collected
into a medium-sized test tube. Once distillation was completed, the heating mantle
was removed to allow the apparatus to cool. Distillate was poured into a separatory
funnel. The distillate was extracted with an equal volume of saturated NaCl solution
(brine). Layers were separated. The organic layer was then transferred into a clean
and dry Erlenmeyer flask. Anhydrous NaSO 4 (5.076 g) was added. The mixture was
filtered into a clean and dry 25 mL round-bottomed flask.
The condenser and vacuum adaptor were rinsed with acetone to remove left
over water from the initial distillation. Two boiling chips were added to the mixture
and it was assembled onto a simple distillation apparatus. The distillate was
collected at approximately 83 oC into a tared, ice-cooled test tube, supported in a
beaker. The Record your yield in grams and calculate your percent yield in your lab
book. Label your sample in this format cyclohexene ABC-010114 (A is the first
letter of the first name of partner 1; B is the first letter of the first name of partner
2; C is the first letter of the first name of partner 3 and 010114 is the month, day
and year when the sample was made). Analyze sample using TLC (eluent 100%
DCM) and IR spectroscopy; record the results and any appropriate calculations in
your lab book.

Results and Discussion:


B
A

Questions:
1. Why is simple distillation important as the final step?
Simple distillation is an important final step because it serves to
remove any remaining cyclohexanol left behind in the previous
steps.
2. If 1-methylcyclohexanol was used, what products would be
synthesized?
The products would be 1-methylcyclohex-1-ene and 1methylenecyclohexane.
3. See Figure 1.
References:

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