Compounds
Sio, Camille; Sison, Gwen; Tolentino, Ana Lou; Tolentino, Rhodelyn; Uy, Kim;
Villanueva, Anna
Group 7, 2F-PH
ABSTRACT
Hydroxyl- and Carbonyl-containing compounds were classified through different tests.
Certain samples that were used in classifying compounds were ethanol, n-butyl alcohol,
sec-butyl alcohol, tert-butyl alcohol, benzyl alcohol, n-butyraldehyde, benzaldehyde,
acetone, acetophenone, isopropyl alcohol and acetaldehyde. The tests performed were
the following: solubility test of alcohols in water, which was used to distinguish which
type of alcohol is miscible or immiscible with water and to determine the amount of
water needed for the solution to produce a homogenous dispersion; Lucas test, which
was used to differentiate primary, secondary, and tertiary alcohols; Chromic acid test to
determine if the sample undergoes oxidation and to classify ketones and aldehydes;
2,4-dinitrophenylhydrazone or 2,4-DNP test, which was also used to identify aldehydes
and ketones; Fehlings test and Tollens silver mirror test were used to find out which
among the tested samples are aldehydes; lastly, iodoform test for the determination of
methyl ketones.
INTRODUCTION
Alcohol is a class of organic
compounds bearing the functional group
OH (hydroxyl) group singly bonded to
a carbon atom, both atoms being sp3
hybridized. Two sp3 hybrid orbitals of
oxygen form sigma bonds to atoms of
carbon and hydrogen. The other two sp3
hybrid orbitals of oxygen each contain
an unshared pair of electrons. The most
important physical property of alcohols
is the polarity of the hydroxyl group,
with oxygen bearing a partial negative
charge and both the carbon and
hydrogen bonded to it bearing partial
positive charge. Alcohols interact with
Figure 2. An aldehyde
Figure 3. A ketone
EXPERIMENTAL
A. Samples used
The samples tested include ethanol, nbutyl alcohol, sec-butyl alcohol, tertbutyl alcohol, benzyl alcohol, nbutyraldehyde, benzaldehyde, acetone,
acetophenone, isopropyl alcohol and
acetaldehyde.
B. Procedure
1. Solubility of Alcohols in Water
Ten drops of each of the alcohol
samples were placed in five previously
labeled (A through E) test tubes with
the aid of a Pasteur pipette. The
alcohols are listed below into the
appropriate tube:
A - ethanol
B - n-butyl alcohol
C - sec-butyl alcohol
D - tert-butyl alcohol
E - benzyl alcohol
One mL of water was added dropwise to
the tube containing the alcohols. The
mixtures were shaken thoroughly after
each addition. When cloudiness resulted
from this, 0.25 mL of water was added
at a time and was vigorously shaken
until a homogenous dispersion resulted.
The total volume of water added was
noted. When no cloudiness resulted
after the addition of 2.0 mL water, it
meant the alcohol was soluble in water.
The results of this procedure were
noted.
2. Lucas Test
To prepare the reagent, 16 g of
anhydrous zinc chloride was dissolved in
10 mL of concentrated HCl. After the
mixture was cooled, about 50 mg (2-3
drops) of the sample was added to 1 mL
of the prepared reagent in a small vial.
The vial was capped and the mixture
was vigorously shaken for a few
seconds and was allowed to stand at
room temperature. This test was
performed on n-butyl alcohol, sec-butyl
alcohol and tert-butyl alcohol. The rate
of the formation of the cloudy
suspension or the formation of 2 layers
was observed.
3. Chromic Acid Test (Jones Oxidation)
The reagent was prepared by dissolving
20 g of chromium trioxide (CrO3) in 60
mL of cold water in a beaker. Twenty
mL of concentrated sulfuric acid was
added to the solution slowly and
carefully with stirring.
Ethanol
n-butyl
alcohol
sec-butyl
alcohol
tert-butyl
alcohol
Benzyl
alcohol
Amount of
water
(in
mL) needed
to produce a
homogenous
dispersion
1 mL
1.75 mL
Solubility
to water
Result observed
miscible
miscible
n-butyl alcohol
Clear solution
sec-butyl alcohol
Clear solution
1 mL
miscible
tert-butyl alcohol
Cloudy suspension
1 mL
miscible
2 mL
immiscible
The table above shows that tertbutyl alcohol readily formed a cloudy
suspension with the addition of the
Lucas reagent compared with n-butyl
and sec-butyl alcohol. This is because
the first sample is a 1 alcohol; the
second a 2; and the third a 3. The
reaction had undergone SN1 reaction,
where a carbocation is formed as an
intermediate product. The stability of
the carbocation is the main factor that
affects the reactivity of alcohols.
Therefore a tertiary alcohol forming the
Result Observed
Blue green solution
Blue green solution
Brownish
yellow
solution
Blue green solution
Table 4. 2,4-dinitrophenylhydrazone
Test
Sample
Acetaldehyde
Benzaldehyde
Acetone
Acetophenone
Result Observed
yellow-orange
precipitate
yellow-orange
precipitate
yellow-orange
precipitate
orange precipitate
Result Observed
Brick red precipitate
Brick red precipitate
No precipitate
No precipitate
Result Observed
Silver mirror
No reaction
Results Observed
Brown precipitate
Yellow crystalline
precipitate
Yellow crystalline
precipitate
REFERENCES
Brown,
W.,
Introduction
international
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(2011).
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student version (5th
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