Dehydration of Cyclohexanol
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Feb 20, 2024
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Dehydration of Cyclohexanol
Nicolas Tapia Stoll (with Gavin Wagner)
Professor Paul Slawek
14
st
March 2023
Introduction:
The purpose of the experiment will be to undergo an elimination reaction of the alcohol cyclohexanol into the alkene cyclohexene through the use of sulfuric acid. They hypothesis for this experiment is that as long as heat is added the compounds of sulfuric acid and cyclohexanol will undergo elimination reactions to produce cyclohexene.
Results:
Cyclohexanol used (mL) and (g)
1mL →
0.962g
Sulfuric acid used (mL) and (g)
0.5mL →
0.645g
Potassium Carbonate used (g)
0.0333g
Mass of cyclohexanol = ?????? ∗ ????𝑖?𝑦 = 1?𝐿 ∗ 0.962
𝑔
??
= 0.962𝑔
(PubChem)
Mass of Sulfuric Acid
= ?????? ∗ ????𝑖?𝑦 = 0.5?𝐿 ∗ 1.290
𝑔
??
= 0.645𝑔
(PubChem)
Moles of Cyclohexanol (mol)
0.0096 mol
Theoretical Yield of cyclohexene (g)
0.789g
Moles of cyclohexanol
=
?𝑎?? (𝑔)
???????𝑎? ??𝑖𝑔ℎ? (
𝑔
?𝑜?
)
=
0.962
100.16
= 0.0096???
Theoretical Yield of cyclohexene = mol cyclohexanol ∗ molecular weight cyclohexene =
0.0096mol ∗ 82.15 (
g
mol
) = 0.789g (PubChem)
Pre-Weighed beaker (g)
13.7175g
Post-weighted beaker (g)
13.9763g
Final Distillate/Experimental Yield
0.249g
Final distillate = 𝑃????𝑖𝑔ℎ??? ?????? − 𝐹𝑖?????𝑖𝑔ℎ??? ?????? = 13.7175 − 13.9763
%Yield
31.6%
%Yield
=
𝐸????𝑖????𝑎? 𝑌𝑖???
𝑇ℎ?????𝑖?𝑎? 𝑌𝑖???
∗ 100 =
0.249𝑔
0.789𝑔
∗ 100 = 31.6%
Final Distillate IR:
Result from Bromine test
: Positive
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Conclusion:
From the experimental results, a few things can be observed to infer the sucees of the experiment. From the IR, the absence of a peak at the wavelengths 3600-3300cm
-1
indicates that there is not an R-OH group in the final compound, meaning it is no longer the cyclohexanol in the final distillate. Additionally, the peak present in the wavelength 2924cm
-1
shows the presence of sp
2
C-H bonds present in the double bond of the cyclohexane.
The positive result of the bromine test also provides evidence of a successful elimination reaction having undergone to produce cyclohexene since the bromine test only would be positive if there were the presence of a double bond in the solution.
The %-yield of the reaction was as seen to be 31.6%, although this is not very large it can still be considered as successful. A couple factors which could have caused the experimental yield to not have been as large as the theoretical yield would have been the possibilities of small human errors in measuring of reactants and compounds, the fact that perhaps the solution mixture of sulfuric acid and cyclohexanol was not heated to completion and left enough time, resulting in to all of the cyclohexene which could have been made, to be produced, etc. Overall though the proper following of the method did lead to a semi-successful experiment.
In conclusion the hypothesis was proved to be correct by the production of cyclohexene in the elimination reaction of cyclohexanol, as proved by the experimental findings.
Bibliography:
U.S. National Library of Medicine. (n.d.). Cyclohexanol
. National Center for Biotechnology Information. PubChem Compound Database. Retrieved April 15, 2023, from https://pubchem.ncbi.nlm.nih.gov/compound/Cyclohexanol#section=Density U.S. National Library of Medicine. (n.d.). Sulfuric Acid
. National Center for Biotechnology Information. PubChem Compound Database. Retrieved April 15, 2023, from https://pubchem.ncbi.nlm.nih.gov/compound/Sulfuric-
acid#section=Density
U.S. National Library of Medicine. (n.d.). Cyclohexene
. National Center for Biotechnology Information. PubChem Compound Database. Retrieved April 15, 2023, from https://pubchem.ncbi.nlm.nih.gov/compound/Cyclohexene#section=Density Appendix:
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Chemical
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Amount used
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100.16
0.9624
1.50 mL
Sulfuric Acid
98.08
1.83
1.00 mL
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Compound
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butanal
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butanoic acid
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write they
question
3. Provide valid resonance structures for the product of
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