SYNTHESIS(OF(4,METHYLCYCLOHEXANE(( ( ( EXPT(110(
Adapted from Pavia, D.L.; Lampmann, G. M.; Kriz, G.S.; Engel, R.G
"Introduction to Organic Laboratory Techniques 3e 1999"
This experiment involved dehydration of a alcohol, 4-methylcyclohexanol, to form
an alkene, 4-methylcyclohexene.
CH3
H3PO4/H2SO4
Δ
OH
Alcohol dehydration reactions are carried out in the presence of catalysts such
such as concentrated sulfuric and phosphoric acid. The equilibrium in this
reaction is shifted to the right by distilling the product off as it is formed. The
product is analyzed by IR spectroscopy
CAUTION: This procedure uses concentrated acids. Be sure to wear gloves
when handling the acids.
PreLab Exercise:
1. Write out a detailed mechanism for the dehydration of 4-methylcyclohexanol
using phosphoric acid as a catalyst.
Synthesis of 4-methylcyclohexene
Tare a 5 mL conical vial and add 1.5 mL 4-methylcyclohexanol. Reweigh the vial
to obtain an accurate weight of the starting alcohol. Add 0.40 mL of 85%
phosphoric acid and 6 drops of concentrated sulfuric acid. Mix the liquids
thoroughly and add a spin vane to the vial. Equip the conical vial with the
Hickman still and the jacketed condenser (in that order, from bottom to top).
Add a small plug of cotton badding to a drying tube, followed by a small amount
of calcium chloride and more glass wool. Attach the drying tube to the top of the
jacketed condenser.
While stirring, heat the mixture carefully until the product begins to distill off. The
distillation should take about 40 minutes. Take care not to heat the mixture too
rapidly. During the distillation, it may be necessary to remove distilled produst
from the well of the Hickman still. If your Hickmane still does not have a side
port, you will need to remove the jacketed condenser to do this. Transfer the
distillate to a clean, dry 3 mL conical vial. Be sure to keep the 3 mL conical vial
capped. The distillation is complete when about 0.5 mL liquid remains in the 5
mL vial and boiling has ceased. Be sure you do not distill to dryness. When the
distillation is complete transfer all of the liquid from the well of the Hickman still to
the 3 mL conical vial.
Isolation of 4-methylcyclohexene
Rinse the sides of the Hickman still with 1.0 mL saturated sodium chloride and
transfer this wash to the vial containing the distillate. Allow the layers to separate
and remove the lower aqueous layer. The sodium chloride solution removes any
phosphoric acid which may have codistilled with the 4-methylcyclohexene and
partially removes and water which may be present in the product. With a dry
pipet, transfer the product to a small test tube and add a few microspatulas of
anhydrous sodium sulfate. Allow the product to dry for 10-15 minutes. Transfer
as much product as possible to a tared vial and obtain the yield of your
methylcyclohexene. Obtain an IR spectrum of your product.
CleanUp
Any concentrated acids should be neutralized to a pH between 6 and 8 and
rinsed down the drain with lots of water. The sodium chloride wash can be
rinsed down the drain. After obtaining an IR spectrum, any remaining product
can be discarded in the NHO waste container.
Final Report
In your Final Report, be sure to include the weight and percent yield for 4-
methylcyclohexene. Attach your IR spectrum with the major peaks labeled. Also
be sure to answer the following questions:
1. Give the names and structures of the major dehydration products for the
following alcohols:
CH3
OH c)
a) b) CH3
OH OH
2. Alcohol dehydrations are catalyzed by concentrated phosphoric and sulfuric
acid. Why are these acids preferable to a simpler acid such as HCl?
Hint: Consider the concentrations of the acids. In addition to the alkene, what
else is produced in the dehydration reaction?
Synthetic Experiment
PreLab Cover Sheet
Name Course and Section
Desk Number Date
Instructor's Name
Grading for Synthetic Experiment PreLab
Pre-Lab Points Points
Possible Missed
Name, Desk#, Course and Section #, Date, TA 3
Name and Experiment Title (abbreviated after
first page)
Summary Experimental Goals 5
Reactions Diagrams of Special Apparatus 5
Chemical Data Table 6
Chromatographic Behavior Comparison of 5
Staring Material and Product
Spectral Features Comparison 5
Explanation of Product Isolation and Purification 6
(Work-Up)
Pre-Lab Exercise 5
Total for Pre-Lab 40
Synthetic Experiment
Final Report Cover Sheet
Name Course and Section
Desk Number Date
Instructor's Name
Grading for Synthetic Experiment Final Report
Final Report Points Points
Possible Missed
Name, Desk#, Course and Section #, Date, TA Name and 2
Experiment Title (abbreviated after first page)
OBSERVATIONS/DATA (Overall organization, readability, 5
completeness)
Weighing data, molecular weights, moles, volumes, details 6
of any analysis conditions
Yield: Show percent yield with limiting reagent clearly 7
indicated
Purity: MP, BP data, color, any other indications of purity
RESULTS/DISCUSSION (Overall organization, readability, 6
completeness)
Results/achievement of goals (did you make the desired 7
product)
Post-Lab Questions 7
Total for Final Report 40
