CHEMISTRY LABORATORY 503
Activity No. 4
Alcohols
Aries Jay Bernal Reyes
MST Chemistry
Date Performed: September 24, 2016
Date Submitted: October 1, 2016
I-
a.Introduction
An alcohol is any organic compound in which the hydroxyl functional group (–
OH) is bound to a saturated carbon atom. The term alcohol originally referred to the
primary alcohol ethanol (ethyl alcohol), the predominant alcohol in alcoholic beverages.
Alcohols are then classified into primary, secondary (sec-, s-), and tertiary (tert-,
t-), based upon the number of carbon atoms connected to the carbon atom that bears the
hydroxyl functional group. (The respective numeric short hands 1°, 2°, and 3° are also
sometimes used in informal settings.).The primary alcohols have general formulas
RCH2OH. The simplest primary alcohol is methanol (CH 3OH), for which R=H, and the
next is ethanol, for which R=CH3, the methyl group. Secondary alcohols are those of the
form RR'CHOH, the simplest of which is 2-propanol (R=R'=CH 3). For the tertiary
alcohols the general form is RR'R"COH. The simplest example is tert-butanol (2-
methylpropan-2-ol), for which each of R, R', and R" is CH 3. In these short hands, R, R',
and R" represent substituents, alkyl or other attached, generally organic groups.
Lucas' reagent is a solution of anhydrous zinc chloride in concentrated
hydrochloric acid. This solution is used to classify alcohols of low molecular weight.
The reaction is a substitution in which the chloride replaces a hydroxyl group. A positive
test is indicated by a change from clear and colorless to turbid, signaling formation of a
chloroalkane.
Chromic acid test distinguishes primary and secondary alcohols from tertiary.
Chromic acid will oxidize a primary alcohol first to an aldehyde and then to a carboxylic
acid and it will oxidize a secondary alcohol to a ketone. Tertiary alcohols do not react.
The OH - bearing carbon must have a hydrogen atom attached. Recall, that a carbon is
oxidized when it loses hydrogen or hydrogens or gains a more electronegative atom.
Since the carbon atom is being oxidized in primary and secondary, the orange chromium
Cr6+ ion is being reduced to the blue - green Cr3+ ion.
Iodoform test does not distinguish 1°, 2°, 3° alcohol but is specific for only one
class of alcohol. This is the secondary methyl alcohol. If the alcohol contains a methyl
group attached to a carbon that also has hydrogen and an OH group then it will give a
positive iodoform test. The formation of a yellow precipitate indicates a positive test.
Acrolein test is used to detect the presence of glycerol or fat. When fat is treated
strongly in the presence of a dehydrating agent like potassium bisulfate (KHSO 4), the
glycerol portion of the molecule is dehydrated to form an unsaturated aldehyde, acrolein
that has a pungent irritating odor.
b. Objective/s:
i. To be able to determine the various types and characteristics of alcohol
c.Statement of the Problem
i. What indications will the various types and characteristics of alcohol give?
ii. What is the significance of alcohols especially in industry, medicine, etc.?
d. Limitation of the Study
i. The experiment is limited only in determining the various classes and
distinguishing characteristics of alcohols
e.Methodology
i. The method used in determining various types and characteristics of alcohol is
done using various test like Chromic acid test, Lucas test, Acrolein test, Special
test for Methyl alcohol, Esterification, and Iodoform test.
II- Results and discussion
1. Chromic acid test
Substance used Reagent used Observation
36 seconds
Ethyl alcohol From orange to green color
solution
1 minute
n – butyl alcohol 5%Potassium From orange to green color
dichromate solution
5% Sulfuric acid
34 seconds
sec – butyl alcohol From orange to green color
solution
tert – butyl alcohol No change occured
Discussion:
Chromic acid test distinguishes primary and secondary alcohols from tertiary.
Chromic acid will oxidize a primary alcohol first to an aldehyde and then to a
carboxylic acid and it will oxidize a secondary alcohol to a ketone. Tertiary alcohols
do not react. The OH - bearing carbon must have a hydrogen atom attached.
2. Lucas test
Substance used Reagent used Observation
5 seconds
tert - butyl alcohol To form an insoluble layer
No change occurred
n – butyl alcohol
Lucas Reagent
No change occurred
sec – butyl alcohol
Benzyl alcohol No change occurred
Discussion:
Lucas' reagent is a solution of anhydrous zinc chloride in concentrated
hydrochloric acid. This solution is used to classify alcohols of low molecular weight.
The reaction is a substitution in which the chloride replaces a hydroxyl group. A
positive test is indicated by a change from clear and colorless to turbid, signaling
formation of a chloroalkane.
3. Esterification
Substance used Reagent used Observation
Ethyl alcohol It produced a smell similar to
banana
Acetic acid
conc. Sulfuric acid
tert – butyl alcohol It produced an unpleasant
odor
Discussion:
Esterification is a reaction between an alcohol and carboxylic acids to make
esters. Esters are derived from carboxylic acids. A carboxylic acid contains the -
COOH group, and in an ester the hydrogen in this group is replaced by a hydrocarbon
group of some kind. Esters are characterized with a fruity smell. In this experiment,
ethyl alcohol was reacted with acetic acid in the presence of sulfuric acid as a
catalyst. It produced a smell similar to a banana. tert – butyl alcohol produced an
unpleasant odor
4. Special test for Methyl alcohol
Substance used Reagent used Observation
Copper coil It produced an oily yellow
Methyl alcohol 0.5 % resorcinol color at the junction of 2
conc. Sulfuric acid layers
Discussion:
5. Iodoform test
Substance used Reagent used Observation
Isopropyl alcohol
Ethyl alcohol Iodine in KI soln.
10% NaOH
Methyl alcohol
Discussion:
Iodoform test does not distinguish 1°, 2°, 3° alcohol but is specific for only one
class of alcohol. This is the secondary methyl alcohol. If the alcohol contains a
methyl group attached to a carbon that also has hydrogen and an OH group then it
will give a positive iodoform test. The formation of a yellow precipitate indicates a
positive test.
6. Acrolein test for glycerol
Substance used Reagent used Observation
Glycerol KHSO4 It produced an unpleasant
odor similar to a burned
grease
Discussion:
Acrolein test is used to detect the presence of glycerol or fat. When fat is treated
strongly in the presence of a dehydrating agent like potassium bisulfate (KHSO 4), the
glycerol portion of the molecule is dehydrated to form an unsaturated aldehyde
III- Conclusion and Recommendation
IV- Answers to Questions
1. What are the classes of alcohol based on the alkyl groups in them? Differentiate
them through their general formulas.
Alcohols fall into different classes depending on how the -OH group is positioned
on the chain of carbon atoms. There are some chemical differences between the
various types. In a primary (1°) alcohol, the carbon which carries the -OH group is
only attached to one alkyl group. In a secondary (2°) alcohol, the carbon with the -
OH group attached is joined directly to two alkyl groups, which may be the same or
different. In a tertiary (3°) alcohol, the carbon atom holding the -OH group is
attached directly to three alkyl groups, which may be any combination of same or
different.
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.
The oxidizing agent used in these reactions is normally a solution of sodium or
potassium dichromate (VI) acidified with dilute sulfuric acid. If oxidation occurs, the
orange solution containing the dichromate (VI) ions is reduced to a green solution
containing chromium (III) ions.
Primary alcohols can be oxidized to either aldehydes or carboxylic acids
depending on the reaction conditions. In the case of the formation of carboxylic
acids, the alcohol is first oxidized to an aldehyde which is then oxidized further to
the acid. Secondary alcohol is oxidized to ketone and Tertiary alcohol having no
reaction because of the absence of alpha hydrogen.
3. What is the significance of Lucas test?
Lucas test is the test for alcohols to differentiate between the primary, secondary
and tertiary alcohols. It takes place by SN1 mechanism. Lucas reagent is the
equimolar mixture of ZnCl2 and HCl. This test is based upon the different reactivity
of alcohols. Tertiary alcohol is the most stable followed by secondary alcohol.
Primary alcohol is least stable. (CH3)3C(OH)+HCl +ZnCl2 → (CH3)3CCl + H2O
Tertiary alcohols and benzylic alcohols react immediately which is reflected by the
appearance of cloudy layer.
4. How will you distinguish ethyl alcohol from methyl alcohol?
The test that will distinguish Ethyl alcohol from Methyl alcohol is the iodoform
test. Only alcohols on C2 carbons give this test (e.g. like ethyl alcohol, 2 - butanol, 2
– pentanol. etc.). Methyl alcohol doesn’t give a response to this test. The alcohol is
reacted with iodine and NaOH which gives a yellow precipitate of methyl iodide.
Only ethyl alcohol gives a posiyive result to this test.
5. What is responsible for the characteristic odor of the acrolein test?
When a fat is heated strongly in the presence of a dehydrating agent such as
KHSO4, the glycerol portion of the molecule is dehydrated to form the unsaturated
aldehyde, acrolein (CH2=CH-CHO), which has the peculiar odor of burnt grease.
6. Give one important commercial method of preparing ethyl alcohol in the Philippines.
Write the chemical reaction involved.
In the Philippines, one commercial method of preparing ethyl alcohol is done using
fermentation. It is type of anaerobic
