School of Natural & Physical Sciences

Chemistry Discipline

Science Foundation Year – Internal Mode

1.10203 Chemistry 1B

Experiment No: 7

Title: Elimination Reaction: Acid-Catalyzed Dehydration of Cyclohexanol to Cyclohexene

Type: Lab report

Name: McAdam TULAPI

Tutorial Group: D2

Tutor: Mr. Lee BEAE

Course Coordinator: Mr. Belly Asong

Week: 8

Date of Experiment: 29-08-23

Date Due: 05-09-23

 Elimination Reaction: Acid-Catalyzed Dehydration of Cyclohexanol to Cyclohexene

INTRODUCTION

Elimination reactions play a crucial role in organic chemistry as they enable the conversion of functional
groups or compounds into more complex structures. Acid-catalyzed dehydration reactions, in particular,
are widely used to generate alkenes through the removal of a molecule of water from alcohol substrates.
The acid catalyst provides the necessary protonation of the hydroxyl group, leading to the formation of a
more reactive species that can undergo elimination.

The acid-catalyzed dehydration of cyclohexanol to cyclohexene is a classic example of an elimination

reaction. Cyclohexanol is a secondary alcohol with the molecular formula C6H11OH, while cyclohexene
is an unsaturated hydrocarbon with the molecular formula C6H10. The elimination of a molecule of water
from cyclohexanol results in the formation of cyclohexene, along with the production of water as a
byproduct.

The use of an acid catalyst is essential for promoting the dehydration reaction. Acid catalysts facilitate the
protonation of the hydroxyl group, weakening the O-H bond and making it easier to abstract a proton.
This proton transfer initiates the elimination of water, as a more stable alkene can be formed. If
cyclohexanol is heated with a catalytic amount of phosphoric acid, elimination of water (dehydration)
results in cyclohexene as the product (Tim Soderberg, 2022). Hence the theory behind this experiment.

OBJECTIVE

➢ To dehydrate cyclohexanol to cyclohexene via an acid-catalyzed elimination reaction.

➢ To employed distillation as a purification technique to separate cyclohexene product from the
reaction mixture.
➢ To determine if Zaitsev’s rule can be applied to this study.

MATERIAL
Chemicals:
Cyclohexanol 21 ml
Brine solution 10 ml
Phosphoric Acid 5 ml
Drying Agents CaCl2 2g
Bromine Water 1 ml
Distilled Water

Apparatus:
100-ml round bottom flask Simple distillation assembly
50-ml collector flask
Separatory funnel
Elementary flask
Ice-water bath
 PROCEDURE

1. About 21 ml of cyclohexanol and 5 ml phosphoric acid (85%) were placed in the 100-ml round
bottom flask.
2. Then the simple distillation assembly was prepared whilst the 50 ml collector flask was kept
immersed in the ice-water bath.
3. The distillation was carried out slowly and stopped when approximately 8 ml of the mixture
remained in the round-bottom during which the water coolant was kept open.
4. The distillate was transferred to the separatory funnel and 10 ml of water, followed by 10 ml of
saturated NaCl (brine) solution, were added. The washes were done quickly.
5. The organic layer was determined by checking the density of cyclohexene and was separated
from the separatory funnel.
6. It was then dried in the Erlenmeyer flask with 2 g of anhydrous CaCl2 for 7 minutes and then the
desiccant was separated from the cyclohexene by decantation.
7. The cyclohexene was quickly collected in the dry 50-ml round-bottom flask and 2-3 boiling chips
were added.
8. Another simple distillation was performed and the fraction was collected on the tared Erlenmeyer
flask, distilling at 78-83 °C. The collecting flask was then immersed in the ice-water bath.
9. Towards the end of the distillation, the liquid in the round-bottom flask was made certain that it
wasn’t distilled to dryness and the product yield was recorded.
10. The small sample of the product was obtained and placed in a small test tube with a few drops of
bromine water to make observation of any color change.

Figure 1. The Reaction Mechanism

 RESULTS

Experimental Data:

Table 1. Results obtained from the procedure, including any necessary computations with respect to the
data.
Cyclohexanol Cyclohexene Yields

Volume 21 ml Boiling Point 83 °C Actual 16.3 g

Mole 0.199 mol Volume 10 ml Theoretical 19.9 g
Density 0.947 g/cm³ Molar Mass 82.143 g/cm³ Percentage 82 %
Molar Mass 100.158 g/mol Color Colorless

Sample Calculation :

(𝑰) 𝑻𝒉𝒆𝒐𝒓𝒆𝒕𝒊𝒄𝒂𝒍 𝒚𝒊𝒆𝒍𝒅

𝑀𝐴𝑆𝑆 (𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑒𝑛𝑒) = 𝑝𝑉

= 0.947𝑔𝑐𝑚−3 𝑥 213 𝑐𝑚

= 19.9𝑔
𝑀𝑜𝑙𝑒𝑠 (𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑎𝑛𝑜𝑙) = 𝑀𝑎𝑠𝑠/𝑀𝑟

= 19.9𝑔/100.158𝑔𝑚𝑜𝑙 −1
= 0.199 𝑚𝑜𝑙

𝑇ℎ𝑒𝑟𝑒𝑓𝑜𝑟𝑒 𝑚𝑜𝑙𝑒𝑠 𝑜𝑓 𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑒𝑛𝑒 = 𝑚𝑜𝑙𝑒𝑠 𝑜𝑓 𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑎𝑛𝑜𝑙 = 0.199 𝑚𝑜𝑙𝑒𝑠

(𝑰𝑰) 𝑨𝒄𝒕𝒖𝒂𝒍 𝒚𝒊𝒆𝒍𝒅

𝑀𝑎𝑠𝑠 𝑜𝑓 𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑒𝑛𝑒 = 𝑚𝑜𝑙𝑒𝑠 𝑥 𝑀𝑟

= 0.199𝑚𝑜𝑙 𝑥 82.145𝑔𝑚𝑜𝑙 −1
= 16.3 𝑔 (𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑒𝑛𝑒)
(𝑰𝑰𝑰) 𝑷𝒆𝒓𝒄𝒆𝒏𝒕𝒂𝒈𝒆 𝒚𝒊𝒆𝒍𝒅

𝑃𝑒𝑟𝑐𝑒𝑛𝑡𝑎𝑔𝑒 𝑦𝑖𝑒𝑙𝑑 = [𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 / 𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑] 𝑥 100

16.3𝑔
= 𝑥 100
19.9𝑔
= 82.0 % 𝑦𝑖𝑒𝑙𝑑 𝑜𝑓 𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑒𝑛𝑒

Using the basic computation in respect to the concept of stoichiometry, the theoretical yield and the
percentage yield was computed.
 DISCUSSION

The acid-catalyzed dehydration of cyclohexanol to cyclohexene proceeded successfully, as evidenced by

the high yield and purity of the collected product. Phosphoric acid was chosen as the catalyst for this
reaction due to its ability to facilitate the elimination of water from the alcohol substrate.

The acid-catalyzed elimination reaction involves the protonation of the hydroxyl group of cyclohexanol
by the catalyst, which leads to the formation of a more reactive species. The protonation weakens the O-H
bond, making it easier to abstract a proton and initiate the elimination of water. The resulting intermediate
is a cyclohexyl oxonium ion, which is a highly unstable species. Rapid rearrangement of the oxonium ion
occurs, leading to the formation of cyclohexene and water. The water molecule is eliminated from the
oxonium intermediate, resulting in the formation of a double bond.

Distillation was employed as a purification technique to separate the cyclohexene product from the
reaction mixture. The boiling point of cyclohexanol is around 161°C, while cyclohexene has a lower
boiling point of approximately 83°C. By gradually heating the reaction mixture, cyclohexanol is
vaporized and condensed, allowing for the collection of the more volatile cyclohexene fraction.

The yield obtained in this experiment was 10 mL of cyclohexene, with a mass of 16.3 g. The high yield
suggests that the reaction proceeded to a substantial extent. However, it is important to note that a small
amount of cyclohexanol may have been lost due to evaporation during the heating and distillation
processes. Nevertheless, the yield obtained indicates the efficiency of the acid-catalyzed dehydration
reaction.

The percentage yield of the collected cyclohexene was determined to be 82% through basic conceptual
computation. This indicates that the desired product was obtained with minimal impurities or side
products. However, this yield may include small amounts of the starting material, cyclohexanol, or other
byproducts of the reaction. Further purification techniques, such as fractional distillation or
recrystallization, could be employed to improve the purity of the cyclohexene product if required.

Additionally, Zaitsev's rule, also known as Saytzeff's rule, states that in a dehydration or elimination
reaction, the major product is the alkene with the most substituted double bond. It assumes that the more
substituted alkene is more stable due to the greater distribution of electron density. In this experiment,
Zaitsev's rule cannot be directly applied due to the presence of a hindered alcohol group. Cyclohexanol
possesses a substituted hydroxyl group, which hampers the attacking nucleophile during the elimination
reaction. The hindered nature of the alcohol group restricts the accessibility of the proton required for the
elimination process. As a result, the reaction may exhibit some deviations from Zaitsev's rule, leading to
the formation of less substituted alkenes in a significant amount.

Nonetheless, the overall success of this acid-catalyzed dehydration reaction provides valuable insights
into the importance of acid catalysis in organic synthesis. Acid catalysts can significantly increase
reaction rates by facilitating the formation of reactive intermediates and lowering the activation energy
required for the elimination process.
 CONCLUSION

In this experiment, the Zaitsev’s rule cannot be directly applied under the given experimental conditions.
Nonetheless, the acid-catalyzed dehydration of cyclohexanol to cyclohexene via distillation was
accomplished successfully. The use of phosphoric acid as the catalyst promoted the elimination of water,
resulting in the formation of cyclohexene. The high yield and purity of the collected product demonstrate
the effectiveness of this elimination reaction. This experiment highlights the importance of acid catalysis
and purification techniques in organic chemistry, and provides a foundation for further investigations into
the optimization of reaction conditions and catalysts for similar elimination reactions. Overall, this
experiment gives a hands-on experience, broadening self comprehension and should be appreciated.
 REFERENCE

o Walter, I, Maya H, Asong, B, B. A laboratory book for chemistry; Oxidation of an Alkene:

Preparation of Adipic Acid from Cyclohexene. (1B course No. 1.10203) University of Papua
New Guinea. 2023. (accessed 2023-09-03)
o Tim Soderberg. Elimination by E1 Mechanism, “June 2022”.
https://www.chem.libretexts.org/Bookshelves/Organic_Chemistry (accessed 2023-09-03)
o Divya Singh. Dehydration of Cyclohexanol. “September 2013” https://www.studocu.com/en-
us/document/lee-college/engineering-physics/cyclo-lab-report/8743113 (accessed 2023-09-03)
o Sadaf Afif. Dehydration of Cyclohexanol. “May 2018” https://www.studocu.com/en-
us/document/brooklyn-college/organic-chem-1-lec/lab-report-cyclohexene/3065939 (accessed
2023-09-03)
o Synthesis of Cyclohexene The Dehydration of Cyclohexanol. (n.d.).
https://www.people.chem.umass.edu/samal/296/cyclohexene.pdf (accessed 2023-09-03)