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Classification Tests For Hydroxyl and Carbonyl Containing Compounds Autosaved
Classification Tests For Hydroxyl and Carbonyl Containing Compounds Autosaved
Classification Tests For Hydroxyl and Carbonyl Containing Compounds Autosaved
Ongchuan, C.F., Martinez, J.G., Ngo, M.C., Pangilinan, A.D., Pantig, P.P., Paulino, R.P.
Group 5, 2KMT, Faculty of Pharmacy
Abstract. Most of the time, organic compounds are insoluble in polar compounds such as, water except for low
molecular-weight amines and oxygen containing compound like: alcohols, carboxylic acids, aldehydes, and
ketones. The main objectives of this experiment is to distinguish whether a compound is hydroxyl- (OH) or
carbonyl- (C=O) containing; to see the distinction between the aldehydes and ketones; to differentiate the three
types of alcohols and to explain the mechanisms involved in the tests. In this conducted experiment hydroxyl
and carbonyl compounds were tested. The samples, ethanol, n-butyl alcohol, sec-butyl alcohol, tert-butyl
alcohol, benzyl alchohol, n-butylraldehyde, benzaldehyde, acetone, acetophenone, isopropyl alcohol and
acetaldehyde, were analyzed by performing several differentiating tests involving their solubility in water such
as: Lucas test, Chromic Acid test, 2,4-Dinitrophenylhydrazone, Fehlings test, Tollens Silver Mirror test, and
Iodoform test. The Lucas test is done to differentiate primary, secondary and tertiary alcohols and gave a visible
turbity in the solution. The chromic acid is performed to see the dissimilarities of ketones and aldehydes in
which the ketones yields a result of s blue-green suspension. The 2-4 dinitrophenylhydrazone test is done as a
collateral for carbonyl groups and therefore gives a visible result of red-orange precipitate or yellow precipitate
for aldehydes and ketones. The Fehlings and Tollens tests are done to pinpoint different positive results of
aldehydes and lastly, the Iodoform test is conducted to to be used as a confirmatory for methyl carboynyl groups
which gives a positive results of yellow crystals or precipitate. Finally, it is proven that the samples used that are
classified as ketones, n-butyraldehyde, benzaldehyde and acetaldehyde are aldehydeswhile acetone and
acetophenone, contain carbonyl groups in their structures. Alcohols that are classified under the hydroxyl
groups are: Ethanol, n-butylalcohol, sec-butyl alcohol, tert -butyl alcohol and benzyl alcohol. The tertiary
alchohols are more stable while the primary alcohols are most polar among the three.
Introduction.
Alcohols are organic molecules containing
the hydroxyl functional group, OH- directly bonded
to a saturated, sp hybridized carbon atom (see
figure 1). Alcohols can be classified as primary (1),
secondary (2), or tertiary (3) depending on the
number of carbon substituents bonded to the
hydroxyl-bearing carbon. Primary alcohols have
the hydroxyl group on a primary (1) carbon atom
(see figure 2), which is bonded to only one other
carbon atom while a secondary alcohol has the
hydroxyl group on a secondary (2) carbon atom,
which is bonded to two other carbon atoms (see
figure 3). Similarly, a tertiary alcohol has the
hydroxyl group on a tertiary (3) carbon atom,
which is bonded to three other carbons (see figure
4). The most important physical property of
Figure 5. Structure of an
aldehyde
Figure 4. Tertiary alcohol 3,
2-methylpropan-2-ol / Tert-butyl
alcohol
A carbonyl group is a functional group
where a carbon atom is double bonded to an oxygen
atom. Because of a difference in the electron
affinities of the carbon and oxygen atoms, the
electron pairs that constitute the double bond are
held closer to the oxygen atom than to the carbon
atom; the electron-rich oxygen atom acquires a
negative charge and the electron-deficient carbon
atom a positive charge. Thus, molecules containing
the carbonyl group are polar. Furthermore, a
Methods.
A.
Sample Compounds
n-butyl alcohol, sec-butyl alcohol,
tert-butyl alcohol, Acetaldehyde, nbutylraldehyde, Benzaldehyde, Acetone,
Acetophenone, Isopropyl alcohol
B.
Procedure
1. Solubility of Alcohols in Water
Five test tubes were labeled from A
to E. With the aid of a Pasteur pipette,
10 drops each of ethanol, n-butyl
alcohol, sec-butyl alcohol, tert-butyl
alcohol, benzyl alcohol were added
into the appropriate test tube. 1 mL of
water was then added dropwise to the
tube containing alcohol, and the
mixture was shaken thoroughly after
each addition. For the results of
cloudiness, 0.25 mL of water was
added at a time with vigorous shaking
until a homogeneous dispersion
resulted. The total volume of water
added was noted. The alcohol was
soluble to water to those results with
no cloudiness obtained after the
addition of 2.0 mL. The results were
noted.
2.
Lucas Test
Lucas reagent was prepared by
dissolving 16g of anhydrous zinc
chloride in 10 mL of concentrated
hydrochloric acid. The mixture was
then allowed to cool. About 50mg(2-3
drops) of the sample were added to
1mL of the reagent prepared in a small
vial. The vial was capped and shaken
vigorously for a few seconds. The
mixture 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
formation of the cloudy suspension or
3.
4.
6.
Fehlings Test
5.
7.
Iodoform Test
2
drops
of
each
sample
(acetaldehyde, acetone, acetophenone,
butyraldehyde, benzaldehyde, and
isopropyl alcohol) were placed into its
own vial. 2O drops of 10% KI
solution was added as well.
Afterwards, 20 drops of fresh chlorine
Alcohol
Condensed
Structural
Formula
Amount of
water needed
Solubility
to
produce
in water
homogenous
dispersion
Ethanol
0.25mL
Soluble
n-butyl
alcohol
1.5mL
Soluble
2mL
Soluble
Secbutyl
alcohol
Tertbutyl
alcohol
1.25mL
Soluble
Benzyl
alcohol
2mL
Insoluble
Alcohol
n-butyl alcohol
Lucas
test
reaction
Clear
colorless
solution
Sec-butyl alcohol
Cloudy solution
Tert-butyl alcohol
Cloudy solution
Alcohol
Alcohol
n-butyl alcohol
Acetaldehyde
Tert-butyl alcohol
Benzaldehyde
Acetaldehyde
No reaction
Benzaldehyde
No reaction
Acetone
Isopropyl Alcohol
Acetone
Acetophenone
2-4
DNP
reaction
Formation
precipitate
Formation
precipitate
Formation
precipitate
Formation
precipitate
test
of orange
of orange
of orange
of orange
Alcohol
Fehlings
reaction
test
Acetaldehyde
Benzaldehyde
Acetone
No reaction
Acetophenone
No reaction
Alcohol
Tollens
mirror
reaction
Acetaldehyde
Silver mirror
Benzaldehyde
No reaction
silver
test
Acetone
No reaction
Acetophenone
No reaction
Alcohol
reaction
Acetaldehyde
Formation
ppt
Benzaldehyde
No reaction
n-butylraldehyde
No reaction
Acetone
Acetophenone
Isopropyl alcohol
test
Formation
ppt
Formation
ppt
Formation
ppt
of
yellow
of
yellow
of
yellow
of
yellow
From the results, only benzaldehyde and nbutylraldehyde failed to give any reaction with the
iodoform test while acetaldehyde, acetone,
acetophenone, and isopropyl alcohol produced a
positive result indicated by the formation of a
yellow precipitate. An alkaline solution of sodium
hypoiodite, formed from sodium hydroxide and
iodine, converted acetaldehyde and aliphatic methyl
ketones into iodoform (haloform reaction). Since
the reagent was also an oxidizing agent, alcohols
which are readily oxidized to acetaldehydes or
methyl ketones also gave a positive reaction. The
mechanism of iodoform synthesis occurred through
ooks/boundless-chemistry-textbook/organicchemistry-23/functional-group-namesproperties-and-reactions-166/alcohols-6387231/
Conclusion.
Once all tests were performed in classifying
certain organic compounds, it can be concluded that
test compounds tested have similar intrinsic
physical properties such as appearance, color, and
physical state. However, in order to classify them
more accurately, they have very distinct odors from
each other. Classification by chemical properties
would be a more accurate basis in differentiating
hydrocarbons.
List of references.
Boundless. Alcohols. Boundless Chemistry.
Boundless, 08 Aug. 2016.
Retrieved
19
Nov.
2016
from
https://www.boundless.com/chemistry/textb