Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
Purpose:
The purpose of this experiment is to synthesize an organic alkene via dehydration of an organic alcohol using a
strong acid catalyst in an E1 elimination reaction. The identity of the final product will be confirmed via
measurement of the refractive index, IR spectroscopy, and a test for the presence of double bonds.
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
Approach:
Determine the mass of cyclohexanol reagent (C6H12O) by weighing. Compute the mass of 85.5% Phosphoric acid
catalyst (H2PO4). Compute the moles of each Cyclohexanol and 85.5% H2PO4. Set up the balanced stoichiometric
equation and determine the molar ratio of the reagents. Determine the limiting reagent. Calculate the theoretical
yield for the synthesis. Assemble simple distillation apparatus and initiate the reaction. Distill the reagents at
~95oC. Saturate the distillate with solid sodium chloride. Add 10% aqueous Sodium carbonate and test with litmus
paper until the distillate is basic (pH>7/blue test result). Wash and separate via liquid/liquid extraction. Dry
product with Anhydrous sodium sulfate. Perform a second simple distillation with the dried product. Determine
the mass of Cyclohexene by weighing. Calculate the percent yield for the reaction Measure the refractive index
using the Abbe refractometer. Compute the adjusted refractive index using the temperature correction factor.
Obtain and analyze an IR spectrum for the product. Test the product and the reagent for double bonds through the
addition of Bromine in Methylene Chloride solution, 1,2-Dimethyloxyethane, and Potassium permanganate.
References
Text
Pavia, D.L., Lampman, G.M., Kriz, G.S., Engel, .G.R., 2011, Introduction to Organic Laboratory
Techniques, A Small Scale Approach, GMU Edition, Chem 315/318, Cengage Learning: pp.179-183
Slayden, S., Stalick, W., Roth, R, 2014, Organic Chemistry Laboratory Manual, 2 nd Edition: Pearson
Custom Publishing: pp. 67-69
Solomons, T.W.G., Fryhle, C.B., Snyder, S.A., 2014, Organic Chemistry, 11th Edition: John Wiley & Sons
Incorporated: pp.303-308
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 1
Mass of Cyclohexanol
Materials
Vial
Cyclohexanol (approx.
10mL)
Results
Equipment
Electronic
balance (0.001)
Calculator
Desc:
Equation Setup:
Mass reagent (g) = Mass reagent+vial (g) Mass
vial (g)
Mass Cyclohexanol
Mass vial
Mass vial + sample
Mass sample
Drawer No.
Course / Section
21
CHEM
315/204
Unk No.
21.154-12.625 =
12.625g
21.154g
8.528g
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 2
Vial 85.5%
Phosphoric acid
(approx. 2.5 mL)
Equipment
Graduated
cylinder
Calculator
Desc:
Equation Setup:
Mass = Density (g/mL) * Vol (mL) * % comp.
(85.5%)
Drawer No.
Course / Section
21
CHEM
315/204
Results
Mass 85.5% H3PO4
Vol (mL)
Density (g/mL)
% Composition
2.4mL
1.71g/mL
85.5%
3.51g
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 3
Course / Section
21
CHEM
315/204
Moles Reagents
Results
Materials
Equipment
Calculator
Desc:
Drawer No.
Moles Cyclohexanol
Mass (g)
M.W. (g/mol)
8.528g
100.158g/mol
8.528 / 100.158 =
0.085145mol
3.51g
96.995g/mol
3.51 / 96.995 =
0.036187mol
Equation Setup:
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
Proc # 4
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
Molar Ratio
1 mol Cyclohexanol
1 mol Cyclohexene
1 : 1
Reaction Mechanism
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc #5
Limiting Reagent
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equipment
Calculator
Desc:
Molar Ratio
Stoichiometric
Experimental
1:1
N/A
Observations:
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 6
Theoretical Yield
Equipment
Calculator
Desc:
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equation Setup:
Where L.R = limiting reagent and M.W =molecular
weight:
Theoretical Yeild
Cyclohexanolol (mol)
Cyclohexene (mol)
M.W. C6H10 (g/mol)
M.W. H2O
0.085145 * 82.143 * 1 =
0.085145 * 18.02 * 1 =
0.085145mol
1
82.143g/mol
18.02g/mol
6.9941g
C6H10
1.5343g
H2O
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
Proc # 7
11/5/15
Balanced
Equation
1 Cyclohexanol
Molecular
100.158g/mol
Weight
Mass
(grams)
Moles
+ 1 H3PO4
Course / Section
21
CHEM
315/204
Results
Desc:
Drawer No.
1 Cyclohexene
+ 1 H2O
96.995g/mol
82.143g/mol
18.02g/mol
8.528g
3.510g
6.9941g
1.5343g
0.08514mol
0.03619mol
0.08514mol
0.08514mol
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 8
Simple Distillation
Materials
85.5%
Phosphoric acid
(approx. 2.5 mL)
Cyclohexanol
(approx. 10mL)
Teflon boiling
chip
Ice water bath
50mL
Distillation flask
25mL
receiving flask
Glass
funnel
Hot plate
Sand bath
Thermomet
er with adapter
Condenser
Distillation
head
Aluminum
plate
Aluminum
foil
Desc:
Course / Section
21
CHEM
315/204
Results
Equipment
Drawer No.
Observations:
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc #9
Measure pH
Sodium
Chloride
10% Sodium
Carbonate aq
Litmus Paper
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equipment
25mL
receiving flask with
distillate
Plastic
pipet
Desc:
Observations:
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 10
Liquid/Liquid Extraction
Materials
Neutralized
distillate
Equipment
25mL
Sepratory funnel
Glass
funnel
Glass
stopper
100mL
Beaker
50mL
Erlenmeyer flask
Desc:
Drawer No.
Course / Section
21
CHEM
315/204
Results
Observations:
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 11
Dry Product
Anhydrous
Sodium Sulfate
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equipment
50mL
Beaker with
Cyclohexene
Desc:
Observations:
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc #12
Simple distillation
Dried
Cyclohexanol
Teflon boiling
chip
Ice bath
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equipment
25mL
Distillation flask
25mL
receiving flask
Glass
funnel
Hot plate
Sand bath
Thermomet
er with adapter
Condenser
Distillation
head
Aluminum
plate
Aluminum
foil
Vial with
cap
Desc:
Observations:
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc #13
Mass Cyclohexene
Cyclohexanol
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equipment
Calculator
Electronic
balance (0.001)
Glass
funnel
Desc:
Mass Cyclohexene
Mass vial
Mass vial + sample
Mass sample
14.248 12.626
12.626g
14.248g
1.622g
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 14
Percent Yield
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equipment
Calculator
Desc:
Percent Yeild
Experimental Yield
Theoretical Yield
6.9941g
1.622g
23.19%
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 15
Refractive index
Cyclohexene
product
Tissue
Alcohol
Dropper
Equipment
Abbe
refractometer (
0.0002)
Desc:
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Unk No.
1.4452
1.4458
1.4455
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc # 16
Drawer No.
Course / Section
21
CHEM
315/204
Materials
Equipment
Calculator
Desc:
Results
Room temp = 23.0oC
Cyclohexene
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
ND20 = 1.445 + (23-20) * 0.00045
ND20 = 1.4469
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc #17
IR Spectroscopy
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Equipment
2 NaCl plates
IR
(salt plate
Spectrometer
Cyclohexene
product
Acetone
KBR (potassium
bromide) pellet
chemwipe
Desc:
IR Spectral Analysis:
Experiment:
Date:
Synthesis of Cyclohexene
11/5/15
Name
Partners
Katheryn Soto
N/A
Proc #18
Cyclohexanol
4 small test
tubes
Cyclohexene
Test tube
product
rack
Bromine in
4 droppers
Methylene Chloride
solution
1,2Dimethyloxyethane
Potassium
permanganate
Desc:
Course / Section
21
CHEM
315/204
Results
Materials
Drawer No.
Observations:
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
KMnO4
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
Summary of Results:
The mass of Cyclohexanol was 8.528 g. The mass of Phosphoric acid was 3.51g. The moles of
Cyclohexanol used were 0.085145mol. The moles of Phosphoric acid used were 0.036187mol. The molar
ratio of Cyclohexanol: Phosphoric acid from the balanced stoichiometric equation was 1:1. The theoretical
yield for the synthesis reaction was 6.9941g of Cyclohexene and 1.5343g of H2O. The mass of Cyclohexene
synthesized was 1.622g. The percent yield for the reaction was 23.19%. The raw refractive index of the
final product was 1.4455D23. The refractive index value calculated to correct for temperature was 1.4469D20.
The IR spectrum obtained showed the following principal absorptions: Saturated alkane CH stretch
<3000cm-1, Unsaturated alkene CH stretch <3000cm-1, CH2 bending absorption at 1450cm-1, C=C alkene
absorption at 1650cm-1, and out of plane CH bending at 1000-650cm-1. An additional broad strong
absorption was shown around 3400cm-1. The Br2 in Methylene Chloride test was positive.
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
Experiment:
Date:
Synthesis of Cyclohexene
Name
Partners
Katheryn Soto
N/A
11/5/15
Drawer No.
Course / Section
21
CHEM
315/204
110-83-8
Cyclohexene
Tetrahydrobenzene
Synonyms
Melting Point
(oC)
Lit -103.5oC
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Boiling Point
(oC)
Lit 82.9oC
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit insoluble
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Density
Rel to Water
Lit 0.811020g/cm-3
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Molecular
Formula
Structural
Formula
C6H10