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Jane Doe
11.10.2021 CHEM 3105-332
Lab Partners:
TA-
Dehydration of Cyclohexanol
Purpose:
Students will synthesize, purify and analyze the product of an acid catalyzed dehydration reaction of
cyclohexanol and see how the reaction converts the reactant to a product by using an E1 reaction.
Data Charts and Tables:

Compounds MW (g/mol) Amount mmol Bp (C) Density (g/mL)

and Reagents
Cyclohexanol 100.16 8mL 79.87 162 .96
H3PO4 97.99 2.5mL 158 1.88
(concentrated)
H2SO4 98.08 5-8 drops 337 1.84
(concentrated)
cyclohexene 82.14 83 .81

Safety:
Cyclohexanol (Danger)
Risk Statements

 Combustible liquid
 Harmful if swallowed
 Causes skin irritation
 Harmful if inhaled
 May cause respiratory irritation
 Harmful to aquatic life with long lasting effects
 Causes serious eye irritation
Safety Statements
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 Keep away from heat/sparks/open flames/hot surfaces.

 No smoking
 Avoid breathing dust/fume/gas/mist/vapors/spray
 Wash face, hands and any exposed skin thoroughly after handling
 Do not eat, drink or smoke when using this product
 Use only outdoors or in a well-ventilated area
 Wear protective gloves/protective clothing/eye protection/face protection
Phosphoric acid (Danger)
Risk Statements:

 Corrosive to metals
 Causes severe skin burns and eye damage
Safety Statements:

 Do not breathe vapors

 Wear protective equipment
 Keep in original container
 Do not eat, drink or smoke when using this product
Sulfuric acid (Danger)
Risk Statements

 May be corrosive to metals

 Causes severe skin burns and eye damage
 May cause respiratory irritation
Safety Statements

 Do not breathe dust/fume/gas/mist/vapors/spray

 Wear protective gloves/protective clothing/eye protection/face protection
 Wash face, hands and any exposed skin thoroughly after handling
Anhydrous magnesium sulfate (Danger)
Risk Statements

 May cause eye, skin, and respiratory tract irritation.

 May be harmful if swallowed, inhaled, or absorbed through the skin.
 Hygroscopic (absorbs moisture from the air).
Safety Statements

 Minimize dust generation and accumulation.

 Avoid contact with eyes, skin, and clothing.
 Avoid ingestion and inhalation.
 Use adequate ventilation.
Bromine dichloromethane solution (Danger)
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Risk Statements

 Causes eye burns.

 Causes skin burns.
 Causes gastrointestinal tract burns.
 Causes chemical burns to the respiratory tract.
Safety Statements

 Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper
and lower eyelids. Get medical aid immediately
 Do not breathe dust, mist, or vapor.
 Do not get in eyes, on skin, or on clothing.
 Do not ingest or inhale. Use only in a chemical fume hood.
 Store in a cool, dry place. Store in a tightly closed container.
0.5 M sodium carbonate
Risk Statements

 N/A
Safety Statements

 N/A
Dichloromethane (Warning)
Risk Statements

 Causes skin irritation

 Causes serious eye irritation
 Suspected of causing cancer
 May cause drowsiness or dizziness
Safety Statements

 Do not handle until all safety precautions have been read and understood
 Avoid breathing dust/fume/gas/mist/vapors/spray
 Wash face, hands and any exposed skin thoroughly after handling
Cyclohexene (Danger)
Risk Statements

 Highly flammable liquid and vapor

 Harmful if swallowed
 May be fatal if swallowed and enters airways
 Toxic to aquatic life with long lasting effects
Safety Statements

 If swallowed rinse mouth. Do NOT induce vomiting

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 Wash face, hands and any exposed skin thoroughly after handling
 If swallowed Immediately call a POISON
 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking
Procedure:
1.In a 50 mL round bottom flask, add 8 mL of cyclohexanol and a PTFE boiling stone. Finish setting up
the simple distillation apparatus. The TA will add 2.5 mL 85% phosphoric acid via syringe followed by
5-8 drops of H2SO4.
2. Heat the reaction mixture starting with a hotplate setting of 350oC. The heat transfer to the round
bottom flask is not efficient and it takes time and heat to drive the reaction. Cool the receiving flask in an
ice bath. The temperature of the hotplate may be raised if necessary.
3.Continue the distillation until about 2-3 mL of liquid remains and nothing seems to distill anymore.
The temperature at the thermometer should also drop as there is no more cyclohexene or water to distill.
4. Transfer the distillate to a separatory funnel and extract it with 3 mL of 0.5 M Na2CO3. There may be
gas evolution so thoroughly swirl the mixture without the stopper in place until there is no gas evolution
before proceeding with the extraction with frequent venting. Drain the aqueous layer (bottom) and test
the pH of the aqueous solution to confirm it is still basic. If it is not, extract with another 3 mL of 0.5 M
Na2CO3.
5. Extract the organic phase in the separatory funnel with ~3 mL of brine (saturated sodium chloride
solution).
6. Carefully dry the organic phase with anhydrous magnesium sulfate using as small amount as needed.
7. Transfer the dried organic phase to a small round bottom flask and distill it into a clean dry pre-
weighed round bottom flask using the same distillation apparatus used in the initial reaction distillation.
This can be accomplished by either rinsing the apparatus used in the first reaction with acetone between
distillations (in the hood) or by setting up a fresh set of clean dry glassware. Start with a hotplate setting
of 200oC. The distillation temperature should not exceed 83oC measured at the opening of the three-way
adaptor assuming the thermometer is good, and the liquid column is not separated inside the thermometer.
8.Dry the outside of the collection flask and weigh by difference to get the purified product yield. Try to
keep the flask stopped as much as possible when it is outside of the hood to minimize how much
cyclohexene evaporates into the lab.
9. Obtain an IR spectrum of the purified product. Since it is a liquid, a drop between two clean NaCl
plates using the transmission module is the ideal means of obtaining the spectrum. IR spectra of the
starting material as well as commercially available cyclohexene are available in the Experiment 11 folder
on the Blackboard course page for comparison. Make sure to note evidence in the spectra for the
conversion of cyclohexanol to your isolated product and that your product is cyclohexene.
Part II: Qualitative Determination of an Alkene
1. To two vials, add 4 drops of cyclohexanol to one and 4 drops of your product to the other.
2. To each vial, add 2-3 drops of bromine in dichloromethane dropwise. Observe any color changes.
The bromine in dichloromethane solution should be initially colored. The resulting mixtures should be
disposed of in the halogenated waste container.
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Observations & Data:

Measurements: Cyclohexanol: 8mL 85% phosphoric acid: 2.5 mL H2SO4: 5-8 drops
0.5 M Na2CO3: 3 mL Bromine: 2-3 drops

 While venting our solution, the difference between the organic and aqueous solutions was small
and this resulted in our solution being unable to be distilled again.
 Temp distilled: 410°C
 When adding the 4 drops of cyclohexanol and product in two vials the one with cyclohexanol
turned brown to yellow and the vial with product turned from brown to colorless

Results & Calculations:

Data from Kayla Tate, Nithin Lalith, and Jake Engemann

 Weight:
- 71.116g (weight of the glass) + 18.995g (weight of the stopper) = 90.111
- 92.5341g (total weight) - 90.111g = 2.4231g (weight of solution)
 Precent Yield:
- 8mL x 0.96 g/mL = 7.96g / 100 = .0768 mol cyclohexanol
- .0768 mol x 82.14 (mw of cyclohexene) = 6.31g cyclohexene (theoretical yield)
- 2.42g solution / 6.31g cyclohexene x 100 = 38.4%
Conclusion/Discussions:
In this experiment there was an E1 reaction partaking in the reaction of turning cyclohexanol to
cyclohexene using dehydration methods. In the spectrometry graph there are major rigid peaks 29000cm-
1 to 31000 cm-1 showing a C-H bonds, a smaller slender peak around 1600cm-1 indicating a C=C double
bond and no C-O bonds showing how the solution completely changed from cyclohexanol to
cyclohexene. With a 38.4% precent yield showed our product contained a great amount of impurities
possible effecting our data. This can be caused by contamination of materials, mistakes when creating the
solution or distillation or the environment effecting our solution when not under the fume hood.
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Post Lab Questions:

1. Which of the following alcohols will undergo dehydration most readily when treated with sulfuric
acid? Explain why.

The third figure will undergo dehydration most readily since it is the most stable carbocation.
2. What is the E1 product of the following compound?

3. What are the elimination products of the following reaction? Which of the products is the major
elimination product?

4. What is the product of the following reaction? Hint: This is a SN1 reaction.

Citations:

 https://beta-
static.fishersci.com/content/dam/fishersci/en_US/documents/programs/education/regulatory-
documents/sds/chemicals/chemicals-o/S25470B.pdf
 https://www.fishersci.com/msdsproxy%3FproductName%3DA300700LB%26productDescription
%3DSULFURIC%2BAC%2BACS%2B700LB%26catNo%3DA300-
700LB%26vendorId%3DVN00033897%26storeId%3D10652
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 https://www.fishersci.fi/store/msds?partNumber=10489750&productDescription=1LT+Sodium+
carbonate+solution+0%2C5M+%281N%29%2C+NIST+Standard+solution+ready+to+use&coun
tryCode=FI&language=en
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6SKU%3DALFAAA11359%26PLANT%3Dd__ALF
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6SKU%3DALFAA42334%26PLANT%3Dd__ALF
 https://pim-resources.coleparmer.com/sds/14522.pdf
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px%3Fpage%3DNewSearch%26LANGUAGE%3Dd__EN%26SUBFORMAT%3Dd__ASNZ%2
6SKU%3DALFAAA17576%26PLANT%3Dd__ALF