Experiment 5: E​1​ Reaction: Dehydration of Cyclohexanol

Date: 11/10/2019

I. Objectives
● To extract cyclohexene from the dehydration of cyclohexanol by simple distillation (1).
● To determine the purity of the synthesized cyclohexene via qualitative tests and infrared
spectroscopy (1).

II. Safety Data Sheet

Chemical Properties, Safety

Reagents Physical Properties
Procedures, Disposal

(2) ● Odorless, white solid. ● It causes eye, skin, digestive,

Sodium hydroxide, ● Soluble in water. and respiratory tract burns.
solid ● BP: 1390 °C ● Hygroscopic.
NaOH ● MP: 318 °C ● Wear complete PPE.
● MW: 40 g/mol ● Do not breathe
● Density: 2.13 g/cm​3 dust/fumes/gas/mist/
vapors/spray.
● Wash skin after handling.

(2) ● Colorless liquid with a pungent, ● Extremely flammable liquid

Propanone irritating odor. and vapor.
Acetone ● Solubility: Miscible. ● Vapor may cause flash fire.
(CH​3​)​2​CO ● BP: 56.05 °C ● Causes eye, skin, and
● MP: -94.7 °C respiratory tract irritation.
● MW: 56.08 g/mol ● Harmful if inhaled. Vapors
● Density: 0.78 g/cm​3 may Cause drowsiness or
dizziness.
● Use with adequate ventilation.
● Wear complete PPE.
● Do not breathe
dust/fumes/gas/mist/
vapors/spray.
● Wash skin after handling.

(2) ● Clear, liquid with strong odor. ● Combustible.

Cyclohexanol ● Soluble in ethanol. ● Causes skin and eye irritation.
C​6​H​12​O ● BP: 161.84 °C ● May cause respiratory
● MP: 25.93 °C irritation.
● MW: 100.158 g/mol ● Containers may explode when
● Density: 0.96 g/cm​3 heated.
● Releases CO and CO​2​ upon
combustion.
● Use only under a chemical
fume hood.
● Harmful if inhaled. Vapors
may Cause drowsiness or
dizziness.
 ● Use with adequate ventilation.
● Wear complete PPE.
● Do not breathe
dust/fumes/gas/mist/
vapors/spray.
● Wash skin after handling.

(2) ● Clear, colorless, odorless liquid. ● Corrosive; causes severe

85% Phosphoric Acid ● Miscible. burns by all exposure routes.
H​3​PO​4 ● BP: 158°C ● Hygroscopic.
● MP: 21 °C ● May cause irreversible eye
● MW: 98 g/mol injury.
● Density: 1.68 g/cm​3 ● Causes severe pain, nausea,
vomiting, diarrhea, and shock.
● Use with adequate ventilation.
● Wear complete PPE.
● Do not breathe
dust/fumes/gas/mist/
vapors/spray.
● Wash skin after handling.

(2) ● Odorless, crystalline white solid. ● May cause eye, skin, and
Sodium chloride ● Soluble in water. respiratory tract irritation.
NaCl ● BP: 1461 °C ● Hygroscopic.
Na — Cl ● MP: 801 °C ● Use with adequate ventilation.
● MW: 58.44 g/mol ● Wear complete PPE.
● Density: 2.165 g/cm​3 ● Wash skin after handling.

(2) ● Colorless liquid with a sweet ● Extremely flammable liquid

Cyclohexene odor. and vapor.
C​6​H​10 ● Insoluble in water. ● Vapor may cause flash fire.
● BP: 82.98 °C ● Causes eye, skin, and
● MP: -103.5 °C respiratory tract irritation.
● MW: 82.143 g/mol ● May form explosive
● Density: 0.81 g/cm​3 peroxides.
● May cause central nervous
system depression.
● Use with adequate ventilation.
● Wear complete PPE.
● Do not breathe
dust/fumes/gas/mist/
vapors/spray.
● Wash skin after handling.

(2) ● White, crystalline solid. ● May cause eye, skin, and

Sodium sulfate ● Soluble in water. respiratory tract irritation.
Na​2​SO​4 ● BP: 1429 °C ● Hygroscopic.
● MP: 884 °C ● Use with adequate ventilation.
● MW: 142.04 g/mol ● Wear complete PPE.
● Density: 2.67 g/cm​3 ● Do not breathe
dust/fumes/gas/mist/
 vapors/spray.
● Wash skin after handling.

III. Procedure
Materials Needed:
● Boiling chips
● Red litmus paper
● Induction stove
● Distillation set-up
● 10-mL graduated flask
● Hot oil bath set up
● Separatory funnel
● Erlenmeyer flask

Process:
1. Set up simple distillation apparatus.
2. Cover receiving flask (RF) with foil and immerse in ice-water bath.
a. + 8g cycloxehanol, + 2mL H​3​PO​4​, + 3-5 boiling chips
3. Round bottom flask.
4. Heat in an oil bath. Maintain temperature between 85-95 ℃.
5. Distill until 2-3mL is left in the RBF.
a. + distillate
6. Separatory Funnel
a. + 5mL portions 3M NaOH saturated with NaCl
7. Continue washing organic layer until aqueous layer is basic.
8. Discard aqueous layer.
a. + organic layer
9. Erlenmeyer flask.
10. Dry over sodium sulfate.
11. Distillation set-up.
a. Acetone
12. Let dry.
13. Distill organic layer at not more than 87℃.
14. Perform qualitative tests (refer to prelab #4) on product.
15. Perform IR spectroscopy on product.

IV. Data and Observations

Mass cyclohexanol, g =
Mass receiving flask, g =
Mass receiving flask + cyclohexene, g =

Compound Cyclohexanol Cyclohexene

 Observations

Qualitative Tests on Cyclohexene (do all mumsh + solubility)

Test Observation/s

Ignition

Baeyer’s Test

Sources:
(1) Guidote A, del Rosario DR, Abuzo AL. Organic Chemistry 1: Laboratory Manual. 2019
Edition. Mostrales DC, Palardonio S, editors. Quezon City, PH: Ateneo de Manila University;
2019.
(2) Fisher Science Education, “SDS Search,” Thermo Fisher Scientific Inc, 2003 [Online].
Available: https://fishersci.com/us/en/catalog/search/sdshome.html.