Arianne Mae Gervacio August 22, 2012

14-A Mr. Elvis Chua

Experiment No. 6: E1 Reaction- Dehydration of Cyclohexanol

I. Objectives
The objective of the experiment was to prepare cyclohexene through the E1
reaction or dehydration of cyclohexanol, and ascertain the presence of cyclohexene
through distillation and various qualitative tests.

II. Introduction
E1 reaction refers to elimination reaction where the rate determining step involves
only one substrate, making it unimolecular. This rate determining step is the formation of
the carbocation. E1 There is competition between the two unimolecular reactions, SN1
and E1, because they both undergo the same dissociation process to form a carbocation,
but when the base attacks the hydrogen of the carbocation, it leads to elimination. On the
other hand, if the nucleophile attacks the carbon, it leads to substitution. In order to solve
this problem the E1 reaction is carried out under a certain number of favorable conditions.
E1 reactions are favored by the use of poor nucleophiles such as weak bases and polar
solvents. Moreover, increasing the temperature of the reaction leads to an E1 reaction.
The mechanism of a secondary and tertiary alcohol involves three steps. First, the alcohol
is protonated by the catalyzing acid. Second, the elimination of water takes place in the
protonated alcohol to form the carbocation. And third, the conjugate base abstracts a
proton from the carbocation to yield an alkene.

In this experiment, cyclohexanol will be used to prepare cyclohexene. The

dehydration of cyclohexanol is an equilibrium reaction; therefore not much of the alkene
will be formed. However, based on Le Chatelier’s principle, the equilibrium may be
shifted towards the formation of products by distilling the alkene from the reaction as
soon as it is formed. The reaction is shown below.

III. Results and Discussion

A. Percent Yield of Cyclohexene
Initial volume Final Volume Percent Yield
8.33mL 4.2mL 50%
From the E1 reaction of 8.0g or 8.33mL of cyclohexanol, 4.2mL of cyclohexene
was formed, which corresponds to a 50% yield. A 100% yield cannot be expected
because there is a competing reaction involved, which is the SN1 reaction of the
carbocation with water to form cyclohexanol. One of the sources of error is the
evaporation of the product, cyclohexene. Cyclohexene is a very volatile compound, which
means it evaporates easily. The flask which held the product was covered with foil and
was placed in an ice bath, but the foil isn’t a very tight cover which might have caused the
product to evaporate. Another source of error is the distillation. It might be possible that
not all of the cyclohexene was allowed to distill, and that there were still some left in the
distillation flask.
 B. Qualitative Tests
Baeyer Test Chromic Acid Test
+ +
Qualitative tests were performed to confirm the presence of cyclohexene. A
positive in the Baeyer’s test shows that cyclohexene was indeed formed because Baeyer’s
test is used to confirm the presence of an alkene. However, a positive was also obtained
from the chromic acid test which means that a primary or secondary alcohol is present.
This shows that the SN1 product, cyclohexanol, is also present in the solution.

IV. Conclusion
4.2mL of cyclohexene was formed from the E1 reaction of 8.0g or 8.33mL of
cyclohexanol. This corresponds to a 50% yield. Various qualitative tests were performed
which confirmed the presence of cyclohexene. The qualitative tests also showed the
presence of cyclohexanol, which is a product of the competing SN1 reaction.

V. Answers to Questions
1. There is a difference between the two reactions. An acid catalyst increases the rate
of a reaction but is not consumed in the reaction. So in the mechanism, the acid
catalyst is regenerated so that it can continue to catalyzed the reaction. It makes
the alcohol group into H2O, which is a better leaving group. In the case of a base
promoted reaction, the acid or base is necessary for the reaction, so it is consumed.

2. The major product obtained from the E1 dehydration of 2-methylcyclohexanol is

1-methylcyclohexene. The acid will attack the alcohol, which will form a
secondary carbocation. It forms two products, 1-methylcyclohexene and 3-
methylcyclohexene. However the major product will be 1-methylcyclohexene
because according to Zaitsev’s rule, the major product that will be formed is the
more stable alkene product that is the alkene with more alkyl substituents on the
double-bond carbons.

3. The role of phosphoric acid is the catalyst in the reaction. Sulfuric acid is not used
because it gives messy results. The use of sulfuric acid produces carbon dioxide
and sulfur dioxide gases. These gases will then have to be removed from the
alkene in order to purify it, which would be a longer process and impractical.

VI. References
Clark, J. (2003). The Dehydration of Alcohols. Retrieved August 23, 2012, from ChemGuide:
http://www.chemguide.co.uk/organicprops/alcohols/dehydration.html

Guidote, A., Del Rosario, D., & Abuzo, A. (2005). Experiencing Organic Chemistry: A
Condensed Laboratory Manual. Quezon City: Ateneo de Manila University.

McMurry, J. (2008). Organic Chemistry. Cengage Learning.