Experiment 7: Alcohols, Ethers and Phenols

ANSWERS TO QUESTIONS

1. Give the balanced equations for all the reactions.

A. Lucas Test
Ethanol + Lucas reagent ZnCl2
C2H5OH + HC l—> C2H5Cl + H2O
Isopropyl alcohol + Lucas reagent ZnCl2
C3H7OH + HCl —> C3H7Cl + H2O
Tert-butanol + Lucas reagent ZnCl2
C4H9OH + HCl —> C4H9Cl + H2O
Benzyl alcohol + Lucas reagent ZnCl2
C7H7OH + HCl —> C7H7Cl + H2O
B. Oxidation of Alcohols
- Ethanol + KMnO4 KMnO
C2H5OH —> C2H4O
- Isopropyl alcohol + KMnO4 KMnO4
C3H8O —> C3H6O
- Tert-butanol + KMnO4 KMnO4
C4H10O —> no observed reaction
- Benzyl alcohol + KMnO4 KMnO4
C7H8O —> C7H6O2
C. Reactions of Phenols
- Phenol + Br2 in water
C6H5O8 +3Br2 H2O
—> C6H2OHBr3 + 3HBr
- Phenol + aqueous neutral KMnO4
KMnO4
C6H5O8 —> C6H4O2

2. Explain why Lucas test is applicable only to alcohols containing 5 or less carbons.
● The Lucas test can only be conducted with alcohols which are soluble in Lucas reagent.
Alcohols with 6 or more carbon atoms are essentially insoluble in Lucas reagent thus the
test cannot be applied to them [1].
3. Explain why tertiary alcohols and ethers cannot undergo oxidation upon reaction with potassium
permanganate.
 ● Tertiary alcohols cannot be oxidized without breaking the molecule’s C-C bonds due to lack
of reactive C-H bonds [2].
4. Explain the relationship between the structures of the phenolic compounds with their expected
pH values.
● Phenolic acidity is enhanced by electron-withdrawing substituents ortho and para to the
hydroxyl group; their influence is stronger in the para-location that it is meta [3].

REFERENCES
[1] Online Lab Manual Home.
http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/Classificatio
nTests/alcohol.html (Accessed September 28, 2019).
[2] Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2017. ChemistryViews. (Accessed September
28, 2019).
[3] Reusch, W. Oxidation of Alcohols. Chemistry.msu.edu, 2013. (Accessed September 30, 2019).