4-Methylcyclohexene Name: _________________________________________
Overall Score
Percent:
Out of 25:
Instructions:
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Unless otherwise indicated, please do not work on these
handouts together, I want to know what YOU know!
Occasionally, you may have to check the course
homepage if you need the data for a particular
experiment
Feel free to use pencil on these handouts
Organic chemists are very visual people, please draw
structures and reactions whenever appropriate (instead
of wordy paragraphs)
Answer the questions completely, no more, no less
Please attach ALL spectra, with peak assignments, to
the back of this handout (if appropriate)
Question
A
Data
B
1
2
3
Question
4
5
6
7
Raw Total
Worth
5
4
3
6
4
3
3
4
4
36
Actual
Data
A. (5 pts)
Measurement
Value
Mass of Cyclohexanol (g)
Volume of 85% H3PO4 (mL)
Number of Drops H2SO4
Theoretical Yield of 4-Methylcyclohexene (g)
Actual Yield of 4-Methylcyclohexene (g)
B. Saturation Tests (4 pts)
Observations
4-Methylcyclohexanol
For !
#1
#2
4-Methylcyclohexene
#3
#4
Bromine
Potassium
Permgangate
Matt Evans
Page 1 of 4
Shasta College
Chemistry 70A
4-Methylcyclohexene
Fall 2014
Questions
1. (3 pts) Why is phosphoric acid added along with sulfuric acid in this reaction?
2. (6 pts) Show the mechanism of this reaction, using arrow-pushing, for this reaction.
What mechanism type is this (SN1, SN2, E1, E2, or addition)?
3. (4 pts) Is this reaction regioselective? How about stereoselective?
Matt Evans
Page 2 of 4
Shasta College
Chemistry 70A
4-Methylcyclohexene
Fall 2014
4. (3 pts) Why is the initial reaction set up as a distillation setup instead of a more normal
reflux setup?
5. (3 pts) What is the purpose of distilling the reaction mixture the second time?
6. (4 pts) Analyze your IR spectrum. How well does it correlate with the Pavia textbook
spectrum? Are there any traces of the original 4-methylcyclohexanol in the spectrum?
(Matt can help you with this analysis.)
Matt Evans
Page 3 of 4
Shasta College
Chemistry 70A
4-Methylcyclohexene
Fall 2014
7. (4 pts) Discuss the results of the unsaturation tests. Were the results consistent with
your expectations? Why or why not?
Matt Evans
Page 4 of 4
Shasta College