ALCOHOLS, ETHERS, AND PHENOLS

Juris Marie G. Garcia

Institute of Chemistry, University of the Philippines, Diliman, Quezon City
Date Performed: February 27, 2015
Date Submitted: March 06, 2015
Answers to Questions:
1.) Balanced equations:
A. Lucas Test
Test Sample
Ethyl Alcohol
Isopropyl Alcohol
Tert-butyl Alcohol
Benzyl Alcohol
B. Oxidation of Alcohols
Test Sample
Ethyl Alcohol
Isopropyl Alcohol
Tert-butyl Alcohol
Benzyl Alcohol
Diethyl Ether
C. Reaction of Phenols
Test Sample
Phenol
p-Nitrophenol
Picric Acid
p-Bromophenol
-Naphthol

Equation
C2H5OH + HCl + ZnCl2 C2H5Cl + H2O
(CH3) 2CHOH + HCl (CH3) 2CHCl + ZnC2 + H2O
(CH3) 3COH + HCl + ZnCl2 (CH3) 3CCl + ZnCl2 +H2O
C6H5CH2OH + HCl + ZnCl2 C6H5CH2Cl +ZnCl2 +H2O

Equation
C2H5OH + KMnO4 CH3COOH + H2O + MnO2 +K+
2(CH3)2CHOH + KMnO4 2(CH3) 2CO + 2H2O + MnO2 + K+
No reaction
C6H5CH2OH + KMnO4 C6H5COOH + H2O +MnO2 + K+
C4H10O + KMnO4 C4H8O2 + H2O + MnO2 + K+

Equation
C6H5OH + 3Br2 C6H5OHBr3 + 3HBr
C6H5OH + KMnO4 C6H4O2 + MnO2 + H2O + K+
FeCl3 + 6C6H5OH [Fe(OC6H5) 6] 3- + 3H+ + 3Cl3C6H5NO3 + FeCl3 Fe(C6H4NO3) 3 + 3HCl
--3BrC6H5OH + FeCl3 Fe(BrC6H4O) 3 + 3HCl
3C10H7OH + FeCl3 Fe(C10H7O)3 + 3HCl

2.) Explain why Lucas test is applicable only to alcohols containing 5 or less carbons
The Lucas reagent is an aqueous solution of strong acid (HCl) and zinc chloride. The
alcohol starting material must be sufficiently soluble in aqueous environments for
the reaction to take place. Having more than 5 carbons would decrease the
compounds solubility. Only water-soluble alcohols with low molecular weight can be
dissolved by the reagent.
3.) Explain why tertiary alcohols and ethers cannot undergo oxidation upon reaction with
potassium permanganate.
Tertiary alcohols does not get oxidized by mild oxidizing agents either in aqueous,
alkaline or under neutral conditions. They undergo oxidation under acidic condition.
Same is true with ethers. Both can only be oxidized under extreme conditions.

4.) Correlate the structure of the phenolic compounds with the measured ph values.

Phenol
Acidp

p-Nitrophenol

Picric

Phenols that contain an -OH group attached to a hydrocarbon are very weak acids.
Their acidity can be virtually ignored. However, phenol must be sufficiently acidic for it
to have recognizably acidic properties - even if it is still a very weak acid. A hydrogen
ion can break away from the -OH group and transfer to a base. Phenol can lose a
hydrogen ion because the phenoxide ion formed is stabilised to some extent. The
negative charge on the oxygen atom is delocalised around the ring. The more stable
the ion is, the more likely it is to form. One of the lone pairs on the oxygen atom
overlaps with the delocalised electrons on the benzene ring.