LICEO DE CAGAYAN UNIVERSITY

Rodolfo N. Pelaez Boulevard, Kauswagan, Cagayan de Oro City

COLLEGE OF PHARMACY
NAME: IRENE L. EMPLEO DATE: 05/10/22

LABORATORY EXPERIMENT 9

ALCOHOLS

I. Objective: At the end of the activity, the students are expected to:
1. Distinguish different tests to identify classification of alcohols.
2. Observe reactivity of different classes of alcohols.

II. Discussion
Alcohols are compounds containing the hydroxyl (OH) functional group bonded
to an alkyl group (-R) and thus, may be represented by the general formula ROH. The
reactivity of alcohols is mainly attributed to the OH group. This functional group has
an inherent acid character shown when the hydrogen is released from the OH bond.
The ease of removal is dependent upon the relative polarization of the OH bond. The
OH group may also be protonated at the oxygen which weakens the C-O bond so that
the whole group may be cleaved off as water and subsequently replaced in the
molecule. Based on the alkyl group, the alcohol may be classified into:
Primary Secondary Tertiary
n-butanol secondary butyl alcohol tertiary butyl alcohol
1-butanol 2-butanol 2-methyl-2-propanol

Primary and secondary alcohols may be distinguished from tertiary alcohol by the
chromic acid test. Primary alcohols are initially oxidized to aldehyde which will be
further oxidized into carboxylic acids, while secondary alcohols are oxidized in
ketones. This is indicated by change in color of the solution from orange into green.
Tertiary alcohols are not readily oxidized by the chromic acid because of the
absence of an alpha hydrogen. To further distinguish the different classes of alcohol,
Lucas test is employed.
Lucas test uses concentrated hydrochloric acid in its lucas reagent. Tertiary
alcohols react immediately to form an immiscible layer of alkyl chloride. The alkyl
chloride is insoluble in the medium and causes the solution to become cloudy before
it separates as a distinct layer. With secondary alcohols, the cloudiness appears after
5 minutes, while primary alcohols do not react under this condition. The reaction
mechanism involved with tertiary and secondary alcohol is substitution.
Another test to distinguish the different classes of alcohol is its reaction with
metals (eg. Na). Primary alcohols react immediately with metals forming alkoxide ion
and liberating hydrogen gas in the solution. Secondary alcohols may also react with
metals but the gas evolution is observed after few more minutes, while tertiary
alcohols do not react under this condition.
 LICEO DE CAGAYAN UNIVERSITY
Rodolfo N. Pelaez Boulevard, Kauswagan, Cagayan de Oro City
COLLEGE OF PHARMACY
III. Procedure
1. REACTION WITH CONCENTRATED HCL (LUCAS TEST)
a. Place in separate test tubes 3mL of 1-butanol (primary), 2-butanol (secondary),
tert-butyl alcohol (tertiary). Then, label the test tubes.
b. Add 1mL of concentrated HCl to each test tubes of alcohols. Place test tubes in a
water bath. Observe the results per test tubes.

Primary Alcohol: No reaction

Secondary Alcohol: There are 2 layers formed as heterogeneous mixture

appeared when it was placed in the water bath.

Tertiary Alcohol: It wasn’t placed in the water bath because there is already a
reaction when it was added with 1ml HCl.

PROVIDE THE COMPLETE CHEMICAL EQUATION INVOLVED IN THE ABOVE REACTIONS:

Primary Alcohol: ZnCl2

CH3CH2CH2CH2OH+HCl No reaction

Secondary Alcohol: ZnCl2

CH3CH(OH)CH2CH3+HCl--------CH3CH(Cl)CH2CH3+H2O

Tertiary Alcohol: ZnCl2

(CH3)3-C-OH + CHl-------(CH3)3-C-Cl+H2O

2. OXIDATION WITH CHROMIC ACID

a. Add 5 drops of K2Cr2O7 solution (mixed with sulfuric acid and water) in each three
separate test tubes.
b. Add 2mL of n-butanol (primary) to the 1st test tube. Observe the results.
The color of the test tubes became black and the temperature is cold.
c. Add 2mL of 2-butanol (secondary) to the 2nd test tube. Observe the results.

The color of the test tube also became black and its temperature is cold

d. Add 2mL of tert-butyl alcohol (tertiary) to the 3rd test tube. Observe the results.
There’s no change in color and in temperature.

PROVIDE THE COMPLETE CHEMICAL EQUATION INVOLVED IN THE ABOVE REACTIONS:

 LICEO DE CAGAYAN UNIVERSITY
Rodolfo N. Pelaez Boulevard, Kauswagan, Cagayan de Oro City
COLLEGE OF PHARMACY
Primary Alcohol:

H3C H3C

K2Cr2O7

H2SO4/H2O OH

OH O

Secondary Alcohol:

OH O

K2Cr2O7

H2SO4/H2O Ketone

Tertiary Alcohol:

CH3

H3C-C-OH K2Cr2O7 No Reaction

H2SO4/H2O
CH3

3. REACTION WITH SODIUM METAL

a. Place in separate test tubes 3mL of ethyl alcohol, 1-butanol (primary), and 2-
butanol (secondary). Then, label the test tubes.
b. Add metallic sodium metal in each test tubes. Then, cover each mouth of the tube
with a balloon. Observe an inflation of the balloon to each test tube. (The inflation
of balloon is due to evolution of the hydrogen gas in the reaction.)
Ethyl Alcohol: The balloon got inflated to upward direction

Primary Alcohol: The balloon got inflated to upward direction

Secondary Alcohol: The balloon got inflated but it didn’t stand to upward
direction

PROVIDE THE COMPLETE CHEMICAL EQUATION INVOLVED IN THE ABOVE REACTIONS:

LICEO DE CAGAYAN UNIVERSITY
Rodolfo N. Pelaez Boulevard, Kauswagan, Cagayan de Oro City
COLLEGE OF PHARMACY
Ethyl Alcohol: 2RO1+2Na-2RONa+H2(g)

Primary Alcohol: RONa+2H2OROH+NaOH

Secondary Alcohol: RONa+2H2OROH+NaOH