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Name: Arlene Jane Chang

Section: A

Locker no. : 7A
Date started/completed: August 31, 2010

Experiment no. 7: Dehydration of Cyclohexanol


Results and Discussion:
There are two keywords important in this experiment, these are: E1 and dehydration.
In order to remove the OH group from cyclohexanol and convert it to cyclohexene, a
reaction called dehydration of alcohols is used (McMurry, 2008). Dehydration is defined by the
Encyclopedia Britannica as a reaction that is carried out by warming the alcohol in the presence
of an acid catalyst. The dehydration process was called E1 because it is an elimination reaction in
which the rate determining step was unimolecular (Carey, 2006). The rate determining step in
this type of reaction is when the leaving group leaves to form an intermediate carbocation.
Generally, the more stable the alcohol the faster the reaction will be (Carey, 2006).
There are three steps in the mechanism of the E1 reaction:
First, by protonating the hydroxyl group, it can leave as a water group. Next, after the
protonation, a carbocation intermediate is formed. Lastly, it is stabilized again by losing the
proton from a carbon atom adjacent to the positively charged carbon ion to yield an alkene
(Encyclopedia Britannica).
Figure 1. Three step mechanism:
OH
H

H
+
H

OH 2

OH 2

H2O

H
H

H 3 PO 4

Figure

Figure 2: General reaction:


OH
H 3 PO 4

H2

In the experiment, the lab manual dictated 8.0 g of solid cyclohexanol was to be used, but
since the lab had only the liquid form, the amount to be used was calculated using density. The

density of cyclohexanol is 0.962 g/mL. By using this equation:

0.962 g 8.0 g
=
1mL
x mL

, the total

amount that was used was 8.32 mL.


The percent yield meanwhile was only 14.42 %. According to Carey, the total yield of
cyclohexene should have been around 79 to 89%. This low output is expected since it is a
reversible reaction it will be subjected to the Le Chateliers Principle. Another reason might be

because some of the cyclohexene might have evaporated and not enough was distillated from the
round bottom flask.
In order to verify the presence of cyclohexene, two qualitative tests were used: Baeyers
test to test the presence of double bond and chromic acid test to see if there are secondary
alcohols in the solution (Ault, 1979).
As expected, the Baeyers test was positive since cyclohexene contained a double bond.
But the chromic test was problematic because it also gave positive result. The positive result in
the Chromic Acid test suggests that there are compounds in the solution that contained secondary
alcohol (Ault, 1979). The goal of this experiment was to get pure (or almost pure) cyclohexene.
This indicated that an error made by the experimenter since there were still some cyclohexanol
left in the solution.

References:
Alcohol. (2010). In Encyclopdia Britannica. Retrieved September 1, 2010, from
Encyclopdia Britannica Online: http://search.eb.com/eb/article-277693
Ault, A. (1979). Techniques and Experiment for Organic Chemistry. Boston,
Massachusetts: Allyn and Bacon
Carey, F. A. (2006). Organic chemistry. Boston, Massachusetts : McGraw-Hill/Higher
Education.
Guidote, A., Del Rosario, D.R., & Abuzo, A.L. (2005). Experiencing organic chemistry:
A laboratory manual. Loyola Heights, QC: Ateneo de Manila University
McMurry, John. (2008). Organic chemistry. Brooks/Cole.