Activity 6

Alcohols
Alcohols are compounds containing the hydroxyl (-OH) functional group bonded to alkyl, 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 case 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 may be cleaved off as a water and subsequently
replaced in the molecule.

Based on the alkyl group, the alcohol may be classified into:

Some examples of these classes of alcohols are:

CH3CH2CH2OH CH3CH2CH(CH3)OH CH3C(CH3)2OH

n-propyl alcohol sec-butyl alcohol tert-butyl alcohol

1-propanol 2-butanol 2-methyl-2-propanol

The most commonly known primary alcohol is ethyl alcohol. It is the alcohol present in alcoholic
beverages. Ethyl alcohol or ethanol is obtained from the fermentation of sugars and starches. The
reaction is catalyzed by the enzyme, zymase, found in yeast.

������
C6H12O6 2 CH3CH2OH + 2CO2

Primary and secondary alcohols maybe distinguished from tertiary alcohols by the chromic acid test.
Primary alcohols are oxidized to aldehydes while secondary alcohols are oxidized to ketones. This is
indicated by the change in color of the solution from orange to green.
 ∆
RCH2OH + H2CrO4 RCHO + Cr3+ + Cr6+
Primary Orange Chromic Aldehyde green
alcohol acid

∆
R2CHOH + H2CrO4 RCOR’ + Cr3+ + Cr6+
Secondary Orange Ketone green
alcohol Chromic acid

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 alcohols, Lucas test is employed. Tertiary alcohols
react immediately to form an immiscible upper 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
these conditions. The reaction mechanism involved with tertiary and secondary alcohol is SN1

Alcohols may be classified based on the number of OH groups as monohydroxy or polyhydroxy

alcohol. Examples of Polyhydroxy alcohols are:

Ethylene glycol Glycerol

1,2-ethanediol 1,2,3-propanetriol

The most important triol is glycerol. It is obtained as a by-product from the manufacture of soap. It is
used as moisturizing agent for cosmetic formulation, in tobacco products, and in food. Glycerol is
detected by the acrolein test. Glycerol undergoes dehydration when heated with KHSO4 to form
propenal (acrolein), which has a pungent odor.
Reagents and Materials:

5ml Methyl alcohol 10ml Conc. Sulfuric acid

10ml Ethyl alcohol 20ml Lucas reagent
10ml n-propyl alcohol 10ml Acetic acid
10ml sec-propyl alcohol 5ml 0.5% Resorcinol
10ml tert-propyl alcohol 5ml Iodine in KI soln.
5ml isopropyl alcohol 10ml 10% NaOH
5ml 5% Potassium dichromate 5ml glycerol
10ml 5% Sulfuric acid 1g Potassium bisulfate

Procedure:
A. Chromic acid Test
1. Into 4 separate test tubes, place 20 drops each of the ff: ethyl alcohol, n-butyl alcohol, sec-butyl
alcohol, and tert-butyl alcohol
2. To each test tube, add 10 drops of 5% potassium dichromate and 10 drops of 5% sulfuric acid.
3. Place all the test tubes in a boiling water bath at the same time. Record the time required for each
solution to change color. Note the change in color and the odor of the product formed

B. Lucas Test
1. Into 4 separate dry test tubes, place 20 drops each of the ff: tert-butyl, sec-butyl alcohol, n-butyl
alcohol
2. To each test tube, add 20 drops of freshly prepared Lucas reagent. Shake only once and let it
stand.
3. Record the time required for the formation of an insoluble layer or emulsion in each of the test
tubes indicating the production of the alkyl halide

C. Esterification
1. Put 20 drops of ethyl alcohol in a dry test tube. Add 10 drops of acetic acid and 5 drops of conc.
Sulfuric acid to it.
2. Warm in a boiling water bath. Note the odor and the time required for the odor to develop
3. Repeat the test with tert-butyl alcohol in place of ethyl alcohol. Compare the results

D. Special Test for Methyl alcohol

1. Mix 10 drops of Methyl alcohol with drops of distilled water in a vial.
 2. Heat a copper coil in the Bunsen burner/alcohol lamp and dip into the methyl alcohol-water
mixture
3. Carefully add 1 drop of 0.5% resorcinol and 10 drops of conc. Sulfuric acid allowing them to
flow down along side of the test tube. Note: Do not shake. Observe the color produced at the
junction of the two layers.

E. Iodoform test
1. To 4 drops of ethyl alcohol, add 4ml of Iodine in Potassium Iodide (KI) soln. Then add drop by
by drop 10% NaOH until the iodine is just discharged.
2. Place the test tube in a warm bath (60oC). Note the odor of the vapors and the color of the
precipitate formed.
3. Repeat the test with: isopropyl alcohol and methyl alcohol in place of ethyl alcohol.

F. Acrolein Test for Glycerol

1. Place 2 drops of glycerol in a dry test tube and add a pinch of Potassium bisulfate, KHSO4
2. Heat the test tube over low flame. Note the odor produced.

Questions:

1. What are classes of alcohols based on the alkyl groups in them? Differentiate them through their
general formulas.
2. Compare the relative ease of oxidation of primary, secondary and tertiary butyl alcohol toward acid
dichromate based on the time required for the solution to change color.
3. What is the significance of the Lucas Test?
4. How will you distinguish ethyl alcohol from methyl alcohol?
5. What is responsible for the characteristic odor of acrolein test?
6. Give one important commercial method of preparing ethyl alcohol in the Philippines. Write the
chemical reaction involved
Name Date

Group no.

Activity 6
Alcohols
I. Chromic acid Test
Test Sample Reagents added Observation

Ethyl alcohol

n-butyl alcohol 5% Potassium dichromate

5% Sulfuric acid

sec-butyl alcohol

tert-butyl alcohol

II. Lucas Test

Test Sample Reagents added Observation

n-butyl alcohol

sec-butyl alcohol
Lucas Reagent

tert-butyl alcohol
III. Esterification
Test Sample Reagents added Observation

Ethyl alcohol

Acetic acid
Conc. Sulfuric acid

tert-butyl alcohol

IV. Special Test for Methyl alcohol

Test Sample Reagents added Observation

Methyl alcohol + 0.5% Resorcinol

Distilled water Conc. Sulfuric acid

V. Iodoform Test
Test Sample Reagents added Observation

Ethyl alcohol

Iodine in KI
Isopropyl alcohol 10% NaOH

Methyl alcohol

VI. Acrolein Test

Test Sample Reagents added Observation

Glycerol Potassium bisulfate