Sei sulla pagina 1di 6

OBJECTIVES:

This experiment aims to:


- Produce cyclohexene through the acid catalyzed elimination of water from
cyclohexanol
- Successfully use the distillation process for the dehydration of cyclohexanol
- Understand mechanism involved in the reaction
- Successfully distill the cyclohexene as soon as it forms to prevent the reverting
back to alcohol

INTRODUCTION:

The dehydration of an alcohol is one way to synthesize alkenes. In the


dehydration of cyclohexanol using phosphoric acid as a catalyst, cyclohexene, an alkene
molecule highly useful in the synthesis of other organic molecules, is produced. This
dehydration process is considered an elimination reaction, when a base attacks the
proton on the adjacent carbon atom of a carbocation to form an alkene. Elimination
reaction is further promoted by heating which allows the reaction to move to an E 1
mechanism. On the other hand, the substitution reaction occurs when a nucleophile
attacks the carbocation. This reaction is used in the substitution of alcohols and is
favored with the use of weakly basic nucleophiles. For this experiment, we will be using
the elimination reaction since the reaction medium is acidic.

PRELAB QUESTIONS:
1. What are the possible side products in the dehydration of cyclohexanol? How is
the formation of these side products minimized/prevented?
The dehydration of cyclohexanol can form the following side products:
dicyclohexyl ethers, polymers, mono and dicyclohexyl sulfate. These side
products can be prevented from forming once the cyclohexene is
protonated with an acid. The distillation process also removes the alkene
from contact with the sulfuric acid, thus acting as the first stage of
purification of the alkene.
2. How is the yield of the reaction maximized? Explain.
The maximization of the yield is done through the removal of the resulting
alkene as soon as it is formed. This is done to prevent the alkene from
reverting back to its alcohol form. Distillation aids in this process since
alkenes have lower boiling points than alcohols or water. It is also possible
to get a good yield if the substitution reaction is suppressed. This is done
through the use of strong acids, a high reaction temperature that favors
elimination, and distillation of cyclohexene from reaction mixture as it is
formed.
3. What is the use of phosphoric acid? Can it be substituted with other acids such as
sulfuric acid or hydrochloric acid? Explain.
Phosphoric acid acts as the catalyst in the E1 dehydration of cyclohexanol.
It protonates the alkene and forms a carbocation which will be attacked by
water in order to form an alcohol. Other strong acids may also be used but
phosphoric acid, since it is an oxidizing agent, os preferred because it
minimizes the loss of the organic compound and the product is not
contaminated with volatile decomposition products.
4. What steps are undertaken to prevent cyclohexene from reverting back to
cyclohexanol? How do these steps prevent reversal from taking place?
The removal of the cyclohexene as soon as it forms prevents the reverting
back to cyclohexanol. This removal displaces the reaction to the right (Le
Chateliers principle) (Pahlavan, n.d.).
5. What are the qualitative tests to verify the presence of cyclohexene and
cyclohexanol? What constitutes a positive test result?
The presence of cyclohexene can be determined through a solubility test,
an ignition test, and a Baeyer test. The Baeyer test must form a reddish-
brown precipitate to confirm the presence of cyclohexene. Meanwhile a
solubility test, a Lucas test, and a Chromic Acid test can be done to
determine the presence of cyclohexanol. The Lucas test must have the
formation of a second phase while the Chromic Acid test must form a blue-
green precipitate.
REAGENTS:
PHYSICAL AND CHEMICAL
REAGENTS SAFETY PRECAUTIONS
PROPERTIES
Cyclohexanol (IUPAC) [C6H12O] Molecular Weight: 100.161 g/mol Has caused adverse reproductive
Boiling Point: 161.84oC and fetal effects in animals
Melting Point: 25.93oC Potential cancer hazard
Density: 0.96 g/cm3 Skin and eye irritant: flush with
Solubility: 42,000 mg/L (10oC) in water for at least 15 mins. then get
water medical assistance
Appearance: Colorless needles or Ingestion (hazardous): do not
viscous liquid with a camphor- induce vomiting unless instructed
like odor by medical personnel
Inhalation (hazardous): to fresh
air, give oxygen, seek medical
assistance
Combustible
Phosphoric Acid (IUPAC) [H3O4P] Molecular Weight: 97.994 g/mol Skin and eye irritant: flush with
Boiling Point: 407oC water if contact
Melting Point: 42.4oC Serious skin contact: Wash with
Density: 1.6850 g/cm3 disinfectant soap and cover
Solubility: Miscible in water contaminated skin with anti-
Appearance: Thick, colorless, bacterial cream. Seek medical aid
odorless, crystalline solid Ingestion (hazardous): do not
induce vomiting unless instructed
by medical personnel
Inhalation (hazardous): remove to
fresh air, give oxygen, seek
medical assistance
Sodium Hydroxide (IUPAC) Molecular Weight: 39.997 g/mol Skin and eye irritant: flush with
[NaOH] Boiling Point: 1388oC water if contact
Melting Point: 323oC Serious skin contact (very
Density: 2.13 g/cm3 hazardous): Wash with
Solubility: 109 g/100mL (20oC) in disinfectant soap and cover
water contaminated skin with anti-
Appearance: Colorless to white bacterial cream. Seek medical aid
solid, colorless liquid, odorless Ingestion: do not induce vomiting
unless instructed by medical
personnel
Inhalation: remove to fresh air,
give oxygen, seek medical
assistance
Corrosive causes 3rd degree burn
Sodium Chloride (IUPAC) [ClNa] Molecular Weight: 58.44 g/mol Skin and eye irritant: flush with
Boiling Point: 1465oC water if contact
Melting Point: 800.7oC Serious skin contact: Wash with
Density: 2.17 g/cm3 disinfectant soap and cover
Solubility: 36.0 g/100g (25oC) of contaminated skin with anti-
water bacterial cream. Seek medical aid
Appearance: Colorless to white Ingestion: do not induce vomiting
crystalline solid, salty taste unless instructed by medical
personnel
Inhalation: remove to fresh air,
give oxygen, seek medical
assistance
Disodium Sulfate (IUPAC) Molecular Weight: 142.04 g/mol Skin and eye irritant (hazardous):
[Na2SO4] Melting Point: 888oC flush with water if contact
Density: 2.67 g/cm3 Serious skin contact: Wash with
Appearance: White powder or disinfectant soap and cover
orthorhombic bipyramidal contaminated skin with anti-
crystals, odorless, bitter saline bacterial cream. Seek medical aid
taste
Ingestion: do not induce vomiting
unless instructed by medical
personnel
Inhalation: remove to fresh air,
give oxygen, seek medical
assistance
REFERENCES:
- GuidoteAM,delRosarioDR,AbuzoAL.ExperiencingOrganicChemistry.QuezonCity:OfficeofResearchand
Publications,AteneodeManilaUniversity;2005.
- [AuthorUnknown].Pubchemcompounddatabase[Internet].USA:NationalCentreforBiotechnologyInformation;
2004September16[updated2017March11;cited2017March12].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/cyclohexanol
- [AuthorUnknown].Sciencelab.com[Internet].USA:Sciencelab.com,Inc.;unknownfirstpublication[cited2017
March12].Availablefrom:http://www.sciencelab.com/msds.php?msdsId=9923625
- [AuthorUnknown].Pubchemcompounddatabase[Internet].USA:NationalCentreforBiotechnologyInformation;
2004September16[updated2017March11;cited2017March12].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/phosphoric_acid
- [AuthorUnknown].Sciencelab.com[Internet].USA:Sciencelab.com,Inc.;unknownfirstpublication[cited2017
March12].Availablefrom: http://www.sciencelab.com/msds.php?msdsId=9927393
- [AuthorUnknown].Pubchemcompounddatabase[Internet].USA:NationalCentreforBiotechnologyInformation;
2005March26[updated2017March11;cited2017March12].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/sodium_hydroxide
- [AuthorUnknown].Sciencelab.com[Internet].USA:Sciencelab.com,Inc.;unknownfirstpublication[cited2017
March12].Availablefrom: http://www.sciencelab.com/msds.php?msdsId=9924998
- [AuthorUnknown].Pubchemcompounddatabase[Internet].USA:NationalCentreforBiotechnologyInformation;
2005March25[updated2017March11cited2017March12].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/sodium_chloride
- [AuthorUnknown].Sciencelab.com[Internet].USA:Sciencelab.com,Inc.;unknownfirstpublication[cited2017
March12].Availablefrom: http://www.sciencelab.com/msds.php?msdsId=9927593
- [AuthorUnknown].Pubchemcompounddatabase[Internet].USA:NationalCentreforBiotechnologyInformation;
2004September16[updated2017March11;cited2017March12].Availablefrom:
https://pubchem.ncbi.nlm.nih.gov/compound/sodium_sulfate
- [AuthorUnknown].Sciencelab.com[Internet].USA:Sciencelab.com,Inc.;unknownfirstpublication[cited2017
March12].Availablefrom: http://www.sciencelab.com/msds.php?msdsId=9927278
- Pahlavan.Chem2423CyclohexeneSynthesis.[UnknownPublication];[UnknownPublicationDate][cited2017March
12].Availablefrom:http://swc2.hccs.edu/pahlavan/2423L9.pdf
-
-
PROCEDURES:

Set up simple distillation apparatus. Cover


receiving flask with aluminum foil and immerse
flask in ice-water bath.

Place 8g of cyclohexanol, 2mL phosphoric acid,


and boiling chips into RBF. Heat mixture and
maintain temperature between 85-95oC. Distill
until 2-3mL is left in RBF.

Pour distillate into separatory funnel and wash it


with 5mL of 3 M NaOH saturated with NaCl.

Continue washing organic layer until aqueous


layer is basic then discard aqueous layers. Decant
organic layer into Erlenmeyer flask and dry it
over sodium sulfate.

Clean distillation setup with acetone and let dry.


Distill organic layer at a temp. not more than 5oC
above boiling point of cyclohexene.

Cyclohexane is very flammable. Keep


Perform qualitative tests and store product in away from direct heat.
scintillating vial. Evaporates easily, diffuses through
cork and dissolves in rubber.
Store in tightly covered screw-cap
vials and keep refrigerated.