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CLASSIFICATION TESTS FOR HYDROXYL- AND CARBONYL-CONTAINING

COMPOUNDS
Divine Caroline S. Natividad, Melchi Esrom L. Opelario, Mark L. Pagulayan, Francia Marie R. Palines,
Gian Mailo V. Quilala, Ruiz A. Rosell
ABSTRACT:
In organic chemistry, there are different functional groups that has certain molecules that are
responsible for their chemical behavior. Examples of functional groups are Hydroxyl and Carbonyl
groups. Carbonyl groups have one Oxygen atom double-bonded to one Carbon atom (C=O), this group is
always seen in aldehydes and ketones while the Hydroxyl groups have one Hydrogen atom single-bonded
to one Oxygen atom (-OH) and this group is always seen in alcohols. Seven classification tests were
given to different compounds: Ethanol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, Benzyl
alcohol, n-Butyraldehyde, Benzaldehyde, Acetone, Acetophenone, Isopropyl alcohol, and Acetaldehyde.
The seven tests were: Solubility of alcohols in water test, Lucas test, Chromic Acid test (Jones Oxidation),
2, 4-Dinitrophenylhydrazine (or 2, 4-DNP) test, Fehlings test, Tollens Silver Mirror test and Iodoform
Test. The solubility of alcohols in water test was only given to Ethanol, n-butyl alcohol, sec-butyl alcohol,
tert-butyl alcohol, and Benzyl alcohol to know their solubility in water. Lucas test differentiated 1, 2,
and 3 alcohols and this test was only given to n-butyl alcohol, sec-butyl alcohol, and tert-butyl alcohol.
Formation of an insoluble alkyl chloride as a cloudy suspension that separates into a distinct upper layer
was the result of this test. Chromic acid test was given to n-butyl alcohol, tert-butyl alcohol,
Acetaldehyde, Benzaldehyde, Acetone, Acetophenone, and Isopropyl alcohol. This test was used in 1, 2,
and 3 alcohols. Appearance of green Cr3+ ion is the result of oxidation and this test was also used to
differentiate ketones from aldehydes. 2, 4-Dinitrophenylhydrazine (or 2, 4-DNP) test was given to
Acetaldehyde, Benzaldehyde, Acetone, and Acetophenone. This test was used to confirm carbonyl
groups; Non-conjugated carbonyl compounds formed yellow hydrazones while conjugated carbonyl
compounds formed orange-red hydrazones. Fehlings test and Tollens Silver mirror test was tested to
Acetaldehyde, Benzaldehyde, Acetone, and Acetophenone. These tests were used to confirm the presence
of Aldehyde; positive result in Fehlings test was deep blue to muddy green solution and gradually a
brick-red precipitate of Cu2O was formed while in Tollens Silver Mirror test was silver mirror. Last test
was the Iodoform test that was tested to Acetaldehyde, n-butyraldehyde, Benzaldehyde, Acetone,
Acetophenone, and Isopropyl alcohol. This test was used to confirm the presence of methyl carbinol and
the positive result was bright yellow precipitate. Based on the said tests, Ethanol, n-butyl alcohol, secbutyl alcohol, tert-butyl alcohol, Benzyl alcohol, and Isopropyl alcohol contains hydroxyl groups while nbutyraldehyde, Benzaldehyde, and Acetaldehyde are aldehydes and Acetone and Acetophenone are
ketones and they are both carbonyl groups.
INTRODUCTION:

Hydroxyl and carbonyl group are


functional groups that were needed to classify in
this said experiment. First, Hydroxyl group is a
functional group that has a hydrogen atom
single-bonded to an Oxygen atom (-OH).
Alcohols are compounds in which one or more
Hydrogen are replaced by OH group in
alkanes. There are three kinds of alcohol:

Primary, Secondary, and Tertiary alcohol. In


primary alcohol, the carbon atom that carries the
-OH group is only attached to one alkyl group.
In secondary alcohol, the carbon atom that
carries the OH group is attached to two alkyl
groups. In Tertiary alcohol, the carbon atom that
carries the OH group is attached to three alkyl
groups.

Next, Carbonyl group has a carbon atom that is


double-bonded to an Oxygen atom (C=O). One
hydrogen atom bonded to C=O is called
Aldehydes while two carbons bonded to the
C=O is called Ketones. The tests that were
included in this said experiments are: Solubility

of alcohols in water test, Lucas test, Chromic


Acid test (Jones Oxidation), 2, 4Dinitrophenylhydrazine (or 2, 4-DNP) test,
Fehlings test, Tollens Silver Mirror test and
Iodoform Test.

In Solubility of Alcohols in Water,


compounds that only have fewer than five
carbon atoms and low molecular-weight is
soluble in water.

hydrazones while conjugated carbonyl


compounds formed orange-red hydrazones. In
this test, the reaction that occurred at the
unsaturated carbonyl group was AdditionElimination in the conversion of Aldehydes and
Ketones.

In Lucas test, an aqueous solution of


Zinc chloride and concentrated HCl is the Lucas
reagent. The reaction that takes place in Lucas
test is SN1 Nucleophilic substitution. Only watersoluble, 1, 2, 3 allylic, 3 alkyl and some 2
alkyl alcohols of low molecular weight gave the
appropriate results in this test.

FIGURE 3: GENERAL MECHANISM OF 2, 4DINITRIPHENYLHYDRAZINE TEST

FIGURE 1: GENERAL MECHANISM OF LUCAS TEST

In Chromic Acid test (Jones Oxidation),


in order for alcohols, ketones and carboxylic
acid to oxidize, Chromic acid is the right reagent
that will give visible results. Appearance of
green Cr3+ ion is the result of oxidation and this
test was also used to differentiate ketones from
aldehydes.

FIGURE 2: GENERAL MECHANISMS OF CHROMIC ACID


TEST

In 2, 4-Dinitrophenylhydrazine test, this


was used to confirm carbonyl groups; Nonconjugated carbonyl compounds formed yellow

In Fehlings test, this was used to


confirm the presence of aldehyde, deep blue to
muddy green solution and a brick-red precipitate
of Cu2O was formed gradually. Only certain
hydroxyketones react in this test not simple
ketones.

FIGURE 4: GENERAL MECHANISM OF FEHLINGS TEST

Tollens Silver Mirror Test is just the same as


Fehlings test, it was used to confirm the
presence of aldehydes and not ketones.
Aldehydes were oxidized to carboxylic acid by
the Tollens reagent and produced a silver mirror
inside the test tube.

Unlike Tollens Silver Mirror test and Fehlings


test, Iodoform test was used test to confirm the
presence of methyl carbinol from ketones and
the positive result was bright yellow precipitate.
Not only ketones can give the positive result,
also the secondary alcohols that were oxidized to
methyl ketones by the iodoform reagent, then
these methyl ketones gave a positive result.

FIGURE 5: GENERAL MECHANISM OF TOLLENS


SILVER MIRROR TEST

FIGURE 6: GENERAL MECHANISM OF IODOFORM


TEST

OBJECTIVES:
The four objectives are [1] to identify whether a compound is hydroxyl- or carbonyl- containing,
[2] to know the difference of the three types of alcohols, [3] to know the difference of aldehydes and
ketones, and [4] to explain the mechanisms in each classifying tests.
METHODOLOGY:
SOLUBILITY OF ALCOHOLS IN WATER:
Five test tubes were labelled from A to
E. Each was placed with 10 drops of alcohol
with the aid of a Pasteur pipette. Test tube A was
Ethanol, B was n-butyl alcohol, C was sec-butyl
alcohol, D was tert-butyl alcohol, and E was
Benzyl alcohol. 1 mL of water was added to
alcohol-containing test tubes and was shaken
thoroughly. When cloudiness or turbidity
appeared, 0.25mL of water was added dropwise,
while vigorously shaking until the result was
homogenous dispersion. The total number of
added water was noted. When there is no
cloudiness or turbidity in the result after adding
2.0mL water, the alcohol was soluble in water
and the results was noted.
LUCAS TEST:
In preparing the reagent, 16g of
anhydrous Zinc chloride was dissolved in 10 mL
concentrated Hydrochloric acid. When the
preparation of reagent was done, 50mg of each
sample (n-butyl alcohol, sec-butyl alcohol, and
tert-butyl alcohol) were added to 1mL of the

reagent in different test tubes. Each test tube was


covered and was shaken vigorously for a few
seconds. The mixtures were allowed to stand at
room temperature and the rate of formation of
the cloudy suspension or formation of two layers
was observed.
CHROMIC ACID TEST (JONES
OXIDATION):
In preparing the reagent, 20g of
chromium trioxide was dissolved in 60mL cold
water in a beaker. While stirring, 20mL of
concentrated Sulfuric acid was added slowly and
carefully to the solution. This reagent was
freshly prepared. The reagent can also be
prepared in a manner where 10% of Potassium
dichromate was mixed with concentrated
Sulfuric acid in 2:1 ratio. After preparing the
reagent, 1 drop of each sample (n-butyl alcohol,
isopropyl alcohol, tert-butyl alcohol,
acetaldehyde, benzaldehyde and acetone) were
put in different test tubes that contain 1mL of
acetone. Next, five drops of the reagent was
added, one drop at a time while shaking the

mixture. For 5 minutes, the test tubes were


placed in a 60c water bath, the color of the
solution was noted.

benzaldehyde, and acetophenone) was added


into different test tubes. The test tubes were
placed in beaker of boiling water and within 1015 minutes, the changes were observed.

2, 4- DINITRIPHENYLHYDRAZINE TEST:
In preparing the reagent, 3g of 2, 4Dinitrophenylhydrazine was slowly added in
15mL of concentrated Sulfuric acid while
stirring to a mixture of 20mL of water and 70mL
of 95% ethanol, it was stirred and filtered. A
drop of each sample (acetone, acetaldehyde,
benzaldehyde, and acetophenone) were placed
into small test tubes separately. Next, 5 drops of
95% of ethanol was added in each test tube was
shaken well. Lastly, 3 drops of 2, 4Dinitrophenylhydrazine was added and when
there was no formation of yellow or orange to
red precipitate, the solution was allowed to stand
for at least 15 minutes.
FEHLINGS TEST:
The Fehlings A reagent was 7g of
hydrated copper (II) sulfate dissolved in 100mL
of water while the Fehlings B reagent was 35 g
of Potassium Sodium Tartrate and 10g of
Sodium hydroxide mixed in 100mL of water.
These two freshly prepared reagents were mixed
and put 1mL of it into different test tubes. 3
drops of each sample (acetaldehyde, acetone,

TOLLENS SILVER MIRROR TEST:


In preparing the reagent, 2 drops of
Sodium hydroxide solution was added to 2mL of
5% silver nitrate solution and mixed thoroughly.
Then, sufficient drops of 2% Ammonium
hydroxide was added until the precipitate
dissolved. 4 test tubes with 1mL of freshly
prepared Tollens reagent was prepared. 2 drops
of each of the samples (acetaldehyde,
benzaldehyde, acetone, and acetophenone) were
added separately. The mixture was shaken and
allowed to stand for 10 minutes. When no
reaction had occurred, the tubes were placed in a
beaker of warm water (35-50c) for 5 minutes.
The observations were recorded.
IODOFORM TEST:
In different test tubes, 2 drops of each
sample (acetaldehyde, acetone, acetophenone,
butyraldehyde, benzaldehyde, and isopropyl
alcohol) was placed. While shaking, 20 drops of
fresh chlorine bleach (5% sodium hypochlorite)
was added slowly to each tube and mixed. The
formation of yellow precipitate was recorded.

RESULTS AND DISCUSSIONS:


SOLUBILITY OF ALCOHOLS IN WATER:
ALCOHOL

CONDENSED
STRUCTURAL
FORMULA

SOLUBILITY IN
WATER

CH3CH2OH
C4H9OH

AMOUNT OF WATER
NEED TO PRODUCE A
HOMOGENOUS
DISPERSION
1 mL
3 mL

ETHANOL
N- BUTYL
ALCOHOL
SEC-BUTYL
ALCOHOL
TERT-BUTYL
ALCOHOL
BENZYL ALCOHOL

CH3CHCH2CH3

1.25 mL

SOLUBLE

(CH3)3COH

1 mL

SOLUBLE

C6H5CH2OH

15 mL

INSOLUBLE

SOLUBLE
INSOLUBLE

TABLE 1: RESULTS OF SOLUBILITY OF ALCOHOLS IN WATER

Only n-butyl alcohol and Benzyl alcohol


were insoluble in this test. Ethanol, sec-butyl
alcohol, and tert-butyl alcohol were soluble in
this test. This follows the principle like
dissolves like. Water is a polar substance as

well as the three alcohols. It also follows the


principle, the lower the number of carbon
atoms, the more soluble or miscible a substance
is.

LUCAS TEST:
SUBSTANCE
N-BUTYL ALCOHOL
SEC-BUTYL ALCOHOL

TERT- BUTYL ALCOHOL

CONDENSED
STRUCTURAL FORMULA
C4H9OH
CH3CHCH2CH3

(CH3)3COH

RESULT
NO PRECIPITATE
NO PRECIPITATE THEN
PRECIPITATED
AFTERWARDS
WHITE PRECIPITATE

TABLE 2: RESULTS OF LUCAS TEST

According to the table above, n-butyl


alcohol was the only soluble alcohol in this test
while the sec-butyl alcohol and tert-butyl
alcohol were insoluble and formed cloudy
suspension or precipitation. The reaction
mechanism of this test is S N1. The secondary
alcohol, sec-butyl alcohol reacted for 2-3

minutes. Tertiary alcohol, tert-butyl alcohol


reacted immediately while primary alcohol, nbutyl alcohol did not have any reaction. It
concludes that the tertiary alcohols react the
most, the secondary alcohols takes time to react
while the primary alcohols react the least.

CHROMIC ACID TEST (JONES OXIDATION):


SUBSTANCE
N-BUTYL ALCOHOL

CONDENSED
STRUCTURAL FORMULA
C4H9OH

TERT- BUTYL ALCOHOL

(CH3)3COH

ACETALDEHYDE
BENZALDEHYDE
ACETONE

CH3CHO
C6H5CHO
(CH3)2CO

ACETOPHENONE

C6H5COCH3

ISOPROPYL ALCOHOL

CH3CHOHCH3

RESULT
EMERALD GREEN
PRECIPITATE
YELLOWISH BROWN
SOLUTION
BLUE GREEN SOLUTION
GREEN SOLUTION
YELLOWISH BROWN
SOLUTION
YELLOWISH BROWN
SOLUTION
BLUE GREEN SOLUTION

TABLE 3: RESULTS OF CHROMIC ACID (JONES OXIDATION) TEST

According to Table 3, N-butyl alcohol,


Acetaldehyde, Benzaldehyde, and Isopropyl
alcohol gave the positive results of this test. The
results were blue green to green solution due to
Oxidation. This test was intended to know if the

substances were capable of oxidizing. Primary


alcohols like N-butyl alcohol and secondary
alcohols like Isopropyl are readily oxidized
while the tertiary alcohol is stable to oxidation.
Also in this test, Aldehydes were differentiated

from Ketones; Aldehydes like Acetaldehyde and


Benzaldehyde gave a positive result while

Ketones like Acetone and Acetophenone were


not oxidized by the oxidizing reagent.

2, 4- DINITRIPHENYLHYDRAZINE TEST:
SUBSTANCE
ACETALDEHYDE

CONDENSED
STRUCTURAL FORMULA
CH3CHO

BENZALDEHYDE

C6H5CHO

ACETONE
ACETOPHENONE

(CH3)2CO
C6H5COCH3

RESULT
YELLOW PRECIPITATE/
HYDRAZONES
YELLOW-ORANGE
PRECIPITATE/
HYDRAZONES
NO PRECIPITATE
ORANGE PRECIPITATE

TABLE 4: RESULTS OF 2, 4- DINITRIPHENYLHYDRAZINE TEST

According to Table 4, only


Acetophenone gave a result of orange precipitate
which means it is a conjugated carbonyl
compound while Acetaldehyde and
Benzaldehyde gave a result of yellow precipitate

which the carbonyl compounds were nonconjugated. In acetone, there was an error in the
result since it did not form any precipitate, it
must be a yellow-orange precipitate.

FEHLINGS TEST:
SUBSTANCE
ACETALDEHYDE

CONDENSED
STRUCTURAL FORMULA
CH3CHO

BENZALDEHYDE
ACETONE

C6H5CHO
(CH3)2CO

ACETOPHENONE

C6H5COCH3

RESULT
BROWN SOLUTIONWITH
RED-BROWN PRECIPITATE
LIGHT BLUE PRECIPITATE
CLEAR BLUE-GREEN
PRECIPITATE
BLUE SOLUTION WITH
OILY LAYER

TABLE 5: RESULTS OF FEHLINGS TEST

According to Table 5, Acetaldehyde and


Benzaldehyde gave a positive result in which the
two substances were Aldehydes while the
Ketones like Acetone and Acetophenone did not
gave the expected result which is brick-red

precipitate. Aldehydes reduced copper, the


solutions turned blue and it slowly formed a
brick-red precipitate while Ketones did not react
in this test.

TOLLENS SILVER MIRROR TEST:


SUBSTANCE
ACETALDEHYDE
BENZALDEHYDE
ACETONE

CONDENSED
STRUCTURAL FORMULA
CH3CHO
C6H5CHO
(CH3)2CO

RESULT
SILVER MIRROR
TURBID WHITE SOLUTION
CLEAR COLORLESS/
MISCIBLE

ACETOPHENONE

C6H5COCH3

CLEAR WITH IMMISCIBLE


GLOBULE

TABLE 6: RESULTS OF TOLLENS SILVER MIRROR TEST

According to Table 6, Acetaldehyde gave the


positive result. Benzaldehyde nearly gave a
positive result but there was a slight error in the
result. The two substances gave a positive result
because were Aldehydes. The Tollens reagent

was reduced by Aldehydes to metallic silver and


was oxidized into corresponding acids. Ketones
like Acetone and Acetophenone did not gave the
positive result because the two substances were
not oxidized by the Tollens reagent.

IODOFORM TEST:
SUBSTANCE
ACETALDEHYDE

CONDENSED
STRUCTURAL FORMULA
CH3CHO

N-BUTYRALDEHYDE
BENZALDEHYDE

CH3CH2CH2CHO
C6H5CHO

ACETONE
ACETOPHENONE

(CH3)2CO
C6H5COCH3

ISOPROPYL ALCOHOL

CH3CHOHCH3

RESULT
REDDISH-BROWN
SOLUTION
CLEAR YELLOW SOLUTION
IMMISCIBLE WITH
REDDISH-BROWN
GLOBULES
YELLOW PRECIPITATE
IMMISCIBLE WITH
REDDISH-BROWN
GLOBULES
CLEAR SOLUTION WITH
YELLOW PRECIPITATE

TABLE 7: RESULTS OF IODOFORM TEST

According to table 7, only Acetone gave


the positive result which was the formation of
yellow precipitate. The mixture of 10% KI

solution and 5% Sodium hypochlorite that was


added to Acetone, converted methyl ketones into
Iodoform by Haloform reaction.

RECOMMENDATIONS AND
CONCLUSIONS:
The apparatus must be prepared before
starting the experiment to make it faster.
Precautionary measures must be followed to
avoid accidents. There was an error in one of our
results. The conclusion was that, the reagent was
not sufficient therefore, the reaction did not took
place. To attain the right results, it was necessary
to repeat the experiment until the right result is
shown.

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