1

Experiment # 10-14
Analysis of Functional Groups: Hydrocarbons, Alcohols & Phenols, Aldehydes & Ketones,
Carboxylic Acid & Acid Derivatives, and Amines

Christian Cruz

Date Performed:
Date Submitted: August 24, 2010
 2

Hydrocarbons
Flammability of Aliphatic and Aromatic Hydrocarbons
Procedure The test samples used and their appearance are as follows:
 Methane, ethylene, and acetylene are colorless gases
 Cyclohexane and toluene are colorless liquids
A test tube containing the sample gas was ignited using a Bunsen
burner flame. The mouth of the tube, when stopper was taken out, was
moved nearer the Bunsen burner flame. When the flame ignited, the
color of the flame and the soot produced were observed.
Reaction Involved
Expected Results
Experimental When the test samples were ignited with a Bunsen burner flame, the
Results / Observations following happened:
 Methane gas did not react since there was no flame color and
soot produced
 Ethylene gas produced an orange flame but no soot
 Acetylene gas produced a bright yellow flame and there was
soot
 Cyclohexane produced a yellow flame but there was no soot
 Toluene produced a yellow flame and soot
Inference

Reaction with Bromine water

Procedure The test samples were methane, ethylene, and acetylene which are
colorless gases.
Bromine water is a yellow brown solution.
1 mL of bromine water was added to the test tube containing the gas
sample then it was stoppered immediately then shaken.
Reaction Involved

Expected Results Bromine water changes from yellow brown to colorless when its
bonds break.
Methane will not react with bromine water since it does not contain a
reactive site.
Ethylene and acetylene are unsaturated compounds which mean that
they have reactive sites therefore; they can react with bromine so a
color change from brown yellow to colorless should be observed.
 3

Experimental When 1 mL of bromine water was added to the samples, the

Results / Observations following happened:
 Methane gas did not react since no color change happened to
the bromine water
 Ethylene gas produced a yellow then colorless liquid
 Acetylene gas produced a pale yellow liquid and smoke
evolved
Inference Methane is saturated (alkene).
Ethylene and Acetylene are unsaturated (alkene and alkyne).

Reaction with Alcoholic Iodine

Procedure The test samples were methane, ethylene, and acetylene which are
colorless gases. Other samples were naphthalene and cyclohexane
which are colorless liquids.
Alcoholic Iodine is a yellow liquid.
2 drops of alcoholic iodine was added to the test tube containing the
sample then it was shaken until a change occurs.
Reaction Involved
Expected Results
Experimental When 2 drops of alcoholic iodine was added to the test samples, the
Results / Observations following happened:
 Methane gas produced a yellow solution
 Ethylene gas produced an orange solution
 Acetylene gas did not react since there was no color change in
the alcoholic iodine
 Naphthalene produced a clear yellow solution
 Cyclohexane produced two immiscible layers: the top layer
was yellow and the bottom layer was clear
Inference Methane is saturated (alkene).
Ethylene and Acetylene are unsaturated (alkene and alkyne).

Baeyer’s Test for Unsaturation

Procedure The test samples were methane, ethylene, and acetylene which are
colorless gases. Other samples were naphthalene and toluene which
are colorless liquids.
Alkaline Potassium Permanganate is a purple liquid.
1 mL of 1% alkaline potassium permanganate was added to the test
tube containing the sample.
Reaction Involved
 4

Expected Results When alkaline potassium permanganate reacts, it reduces to

manganese dioxide which is a brown solid.
Methane will not react with alkaline potassium permanganate since it
does not contain a reactive site.
Ethylene and acetylene are unsaturated compounds which mean that
they have reactive sites so they can react with alkaline potassium
permanganate so a color change from purple to brown should be
observed.
Naphtalene and Toluene are aromatic compounds which means that
they can undergo substitution reaction therefore they can react with
alkaline potassium permanganate so a change should be observed.
Experimental Results/ The following happened when 1% alkaline potassium permanganate
Observations was added to the samples:
 Methane gas did not react with potassium permanganate since
there was no color change
 Ethylene gas produced a chocolate brown solution
 Acetylene gas produced a dark brown solution with dark
brown precipitate
 Naphthalene produced a violet solution with purple precipitate
 Toluene produced two immiscible layers: the top layer was
clear and the bottom layer was purple
Inference Methane is saturated (alkene).
Ethylene and Acetylene are unsaturated (alkene and alkyne).

Formation of Copper Acetylide

Procedure The test samples were methane, ethylene, and acetylene which are
colorless gases.
Ammoniacal cuprous chloride is a dark blue solution.
5 mL of ammoniacal cuprous chloride was added to a test tube
containing the sample then; it was covered by a stopper and shaken.
Reaction Involved CuCl
C2H2 CuC2H2 + 2HCl
Expected Results
Experimental When 5mL ammoniacal cuprous chloride was added to methane and
Results / Observations ethylene, there was no reaction since the ammoniacal cuprous chloride
remained dark blue.
When 5mL ammoniacal cuprous chloride was added to acetylene,
 5

brown precipitates were produced which are sticking at the sides of the
test tube.
Inference

Reaction of Bromine with Aromatic Hydrocarbon

Procedure The sample used is toluene which is a clear liquid.
Bromine in chloroform is a light yellow liquid.
1 mL of toluene was placed into two separate test tubes. Each test tube
was added with bromine in chloroform until a faint yellow color was
obtained then, one test tube was placed under the sun and the other
was moved in a dark place (inside the locker).
Reaction Involved

UV
Expected Results Bromine will react to an aromatic compound by substitution if it is
initiated by producing bromine radicals through UV light. When
bromine forms radicals, or when their bond is broken, there will be a
color change from light yellow to colorless. This means that a color
change should happen in the test tube, with bromine in chloroform and
toluene, which is placed under the sun.
Experimental When toluene and bromine in chloroform was mixed, the solution
Results / Observations produced was dark brown.
The test tube, which was placed inside the locker (a place without
sunlight), containing toluene and bromine in chloroform remained
dark brown in color.
The test tube, which was placed under the sun, containing toluene and
bromine in chloroform became colorless.
Inference Bromine only reacts with aromatic hydrocarbons when initiated with
UV light coming from the sun.

Action of Nitric Acid with Aromatic Hydrocarbon

Procedure The samples used were toluene and cyclohexane which are colorless
liquids.
Concentrated sulfuric acid and Nitric acid solutions are colorless
liquids.
6 drops of sample was added to a test tube containing 2 mL of
concentrated sulfuric acid and 1 mL of concentrated nitric acid. The
test tube was heated through a water bath for 10 minutes and it was
cooled then; the contents were poured in 10 mL ice water.
Reaction Involved
Expected Results
 6

Experimental When concentrated sulfuric acid and concentrated nictric acid were
Results / Observations added to the samples, the following were observed:
 In toluene, two colorless immiscible layers formed.
 In cyclohexane, two immiscible layers formed: the top layer is
yellow and the bottom layer is clear.
When the solutions were heated using a water bath and poured to ice
water, the following happened:
 The toluene solution still remained colorless and white vapor
evolved
 The cyclohexane solution turned milky white and white vapor
evolved
Inference

Alcohols & Phenols

Sodium Detection for Acid Hydrogen
Procedure Sodium metal is a grayish white solid.
The dry alcohol sample was prepared by adding a pinch of anhydrous
magnesium sulfate to 95% ethanol then the solution was decanted. The
solution produced was a colorless liquid.
Sodium metal was added to the sample and the mixture was heated
through water bath then, 1 mL of water was added and the solution
was tested using litmus paper.
Reaction Involved
Expected Results When sodium metal reacts with alcohol, hydrogen gas is liberated,
indicated by bubble formation. The reaction between dry alcohol and
sodium metal should produce bubbles due to the formation of acid
hydrogens (then hydrogen gas) and a basic solution die to the
formation of a sodium compound.
Experimental When sodium metal and water were added to the dry alcohol and after
Results / it was cooled, bubbles were produced at the surface of the settled
Observations sodium metal.
Inference Acid hydrogen is present in the dry alcohol sample.

Comparison of Oxidizing Conditions

Procedure The sample was ethyl alcohol which is a colorless liquid.
6M sulfuric acid and 6M sodium hydroxide are colorless liquids.
1 % potassium permanganate is a purple solution.
5 drops of ethyl alcohol and 2 mL of water were mixed in each three
test tubes. One test tube was added with a drop of 6M sulfuric acid,
the other test tube was added with 6M sodium hydroxide, and the last
test tube was kept constant. Simultaneaously, 2 drops of 1 %
potassium permanganate solution was added to the three test tubes.
 7

Reaction Involved
Expected Results
Experimental When 1% potassium permanganate was added to ethyl alcohol with
Results / Observations 6M sulfuric acid and 2 mL water, the solution produced was pink.
When 1% potassium permanganate was added to ethyl alcohol with
6M sodium hydroxide and 2 mL water, the solution produced was
green
When 1% potassium permanganate was added to ethyl alcohol with 2
mL water, the solution produced was pink.
Inference

Comparison of Oxidation Rates of Alcohols

Procedure The samples used were ethanol, isopropyl alcohol, tertbutyl alcohol,
and phenol which are colorless liquids.
Potassium dichromate is a yellow solution.
Sulfuric acid is a colorless solution.
1 mL of samples were placed in different test tubes. The samples are
oxidized by adding 6M sulfuric acid and 5 drops of 1% potassium
dichromate solution in each of the test tubes simultaneously.
Reaction Involved [O] is potassium dichromate which serves as an oxidizing agent and
reduces:

Expected Results When potassium dichromate reduces, a green solution is formed.

Primary and secondary alcohols are able to oxidize in the presence of
potassium dichromate since they have enough hydrogen atoms
attached to the carbon in the hydroxyl group to perform an oxidation
reaction. Tertiary alcohols and phenols do not have hydrogen atoms
attached to the carbon in the hydroxyl group which means that it
cannot be oxidized. Ethanol and isopropyl alcohol will only produce a
green product.
Experimental When sulfuric acid and potassium dichromate were added to the test
Results / Observations solutions, the following changes occurred:
 Ethanol and isopropyl alcohol produced a blue green solution.
 Tertbutyl alcohol produced a yellow orange solution.
 Phenol produced a cloudy white solution then it turned black
 8

brown.
Inference Ethanol and isopropyl alcohol are primary and secondary alcohols,
respectively.

Ceric Nitrate Test for Alcohols

Procedure The samples used were ethanol, isopropyl alcohol, water, and
tertbutyl alcohol which are colorless liquids.
10 drops of sample was added to 1 mL ceric nitrate solution.
Reaction Involved

Expected Results When alcohols react with cerric nitrate, an alkoxy cerium(IV)
compound is formed which is indicated by a red product. Ethyl
alcohol, isopropyl alcohol, and tertbutyl alcohol should change into a
red solution.
Experimental When 1 mL ceric nitrate was added to the samples, the following
Results / Observations changes happened:
 Ethyl alcohol, isopropyl alcohol, and tertbutyl alcohol turned
dark orange
 Water turned yellow
Inference Ethyl alcohol, isopropyl alcohol, and tertbutyl alcohol are alcohols.

Chromic Acid test for Distinguishing 10 and 20 alcohols from Tertiary

Alcohols
Procedure The samples used were ethanol, isopropyl alcohol, tertbutyl alcohol,
and phenol which are colorless liquids.
Chromic acid is a dark yellow solution.
Acetone is a colorless liquid.
2 drops or 50 mg of sample was added with 1 mL reagent grade
acetone and 4 drops of chromic acid.
Reaction Involved

Expected Results When chromic acid oxidizes, it turns into a green solution.
Only primary alcohols, secondary alcohols, and phenol are capable of
oxidizing chromic acid therefore a change in color should be only
observed in ethanol, isopropyl alcohol and phenol.
Experimental When acetone and chromic acid was added to the test samples, the
 9

Results / Observations following happened:

 Ethanol produced a yellow brown solution with green and
black precipitates.
 Tertbutyl alcohol produced a clear orange solution with a small
black immiscible bottom layer.
 Isopropyl alcohol produced a brown solution with green
precipitate and black immiscible bottom layer.
 Phenol produced a dark brown solution with brown
precipitates.
Inference Ethanol, isopropyl alcohol, and Phenol are primary alcohol, secondary
alcohol, and phenol, respectively.

Lucas Test for Determining 10,20, and 30 alcohols

Procedure The samples used were ethanol, isopropyl alcohol, and tertbutyl
alcohol which are colorless liquids.
1 mL of Lucas reagent was added to each of three test tubes. ethanol,
isopropyl alcohol, and tertbutyl alcohol were added to the three test
tubes then they were covered by a stopper and shaken.
Reaction Involved
Expected Results When the Lucas reagent, containing zinc chloride and hydrochloric
acid, is reacted with an alcohol, the alcohol forms a carbocation. The
formation of a carbocation, indicated by the formation of an
immiscible layer, is easier if it is more stable in that state. By
hyperconjugation and inductive effect, tertiary alcohols will produce a
carbocation faster then followed by secondary and primary alcohols,
respectively. This means that an immiscible layer will occur faster
with tertbutyl alcohol then isopropyl alcohol and ethanol, respectively.
Experimental When 1 mL of Lucas’s reagent was added to the test samples two
Results / Observations immiscible layers formed: a clear bottom layer and a white top layer.
Tertbutyl alcohol formed the immiscible layers the fastest followed by
isopropyl alcohol then the slowest to form the immiscible layers is
ethanol.
Inference Tertbutyl alcohol, isopropyl alcohol, and ethanol are tertiary,
secondary, and primary alcohols, respectively.

Acidity of Phenols
Procedure The samples used were phenol, acetic acid, and ethyl alcohol. Phenol
is a white wet amorphous solid that easily melts into a clear viscous
liquid. Acetic acid and ethanol are colorless liquids.
10% sodium bicarbonate solution is a colorless liquid.
50 mg or 5 drops of sample was added to 0.5 mL of distilled water.
The solution was tested with litmus paper then it was poured to 1 mL
of 10% sodium bicarbonate solution.
 10

Reaction Involved
Expected Results
Experimental When water was added to the sample and tested with litmus paper, the
Results / Observations following were observed:
 Phenol made red litmus paper into blue which makes it basic
 Acetic acid made blue litmus paper to red which makes it
acidic
 Ethanol made blue litmus paper to red which makes it acidic
When 10% sodium bicarbonate was added to the samples, the
following changes happened:
 Phenol produced a colorless solution with cloudy white
precipitates. Bubbles evolved but disappeared.
 Acetic acid formed a clear solution with precipitates. Bubbles
evolved.
 Ethanol formed a colorless solution with no bubbles and no
precipitates.
Inference

Reaction of Phenols with Bromine water

Procedure The sample used is phenol which is a white wet amorphous solid that
easily melts into a clear viscous liquid.
Bromine water is a yellow brown solution.
10 drops of bromine water was added to 5 drops of phenol in a test
tube.
Reaction Involved

Expected Results When bromine water reacts with phenol, a white precipitate should be
formed. This white precipitate is 2,4,6-tribromophenol.
Experimental When 10 drops of bromine water was added to 5 drops of phenol, the
Results / Observations solution produced became milky white with suspended white
precipitates.
Inference Phenol reacted with bromine water to produce a white precipitate
which is 2,4,6-tribromophenol.

Ferric Chloride test for water soluble Phenols

Procedure The samples used were phenol, ethanol, resorcinol, hydroquinone,
acetic acid, and salicylic acid. Ethanol and acetic acid are colorless
liquids. Phenol is a white wet amorphous solid that easily melts into a
clear viscous liquid. Resorcinol, hydroquinone, and salicylic acid are
white crystals.
 11

Ferric chloride is a yellow solution.

A drop of sample was dissolved in 1 mL ethyl alcohol then 4 drops of
1% ferric chloride was added to the solution.
Reaction Involved

Expected Results When phenols are reacted with ferric chloride, a colored complex is
produced. The colored complex should either be red, blue, green, or
purple. This means that phenol, resorcinol, salicylic acid, and
hydroquinone should produce a colored product.
Experimental When Ferric chloride and ethanol was added to the samples the
Results / Observations following changes happened:
 Phenol produced a clear dark green brown solution
 Ethanol produced a clear yellow solution
 Resorcinol produced a dark green solution
 Hydroquinone produced a dark brown solution
 Acetic acid produced a clear yellow solution
 Salicylic acid produced a dark purple solution
Inference Phenol, resorcinol, salicylic acid, and hydroquinone are phenols.

Aldehydes & Ketones

Oxidation of Aldehydes with Potassium Permanganate
Procedure The samples used were acetone, formaldehyde, cyclohexanone, and
benzaldehyde which are colorless liquids.
Potassium permanganate is a purple liquid.
5 drops of 1% potassium permanganate was added to 1 mL distilled
water and 4 drops or 50 mg sample. When no reaction occurred, of 6M
sodium hydroxide was added.
Reaction Involved
Expected Results
Experimental When the samples were oxidized using potassium permanganate and
Results / Observations water was added, the following changes happened:
 Acetone did not react so 3 drops of 6M sodium hydroxide was
added then the solution turned green with brown precipitates.
 Formaldehyde produced a red solution then it turned brown
and then turned into a colorless solution with precipitates.
 Cyclohexanone produced a bright red solution then it turned
dark brown.
 Benzaldehyde produced a dark red solution then it turned
brown with precipitates.
Inference
 12

2,4 – Dinitrophenylhydrazine test for Aldehydes and Ketones

Procedure The samples used were acetone, formaldehyde, cyclohexanone, and
benzaldehyde which are colorless liquids.
2,4-Dinitrophenylhydrazine is an amber solution
1 mL of 2,4-Dinitrophenylhydrazine was added with 2 drops or 25 mg
of sample.
Reaction Involved

Expected Results When an aldehyde or ketone reacts with 2,4-Dinitrophenylhydrazine,

through a nucleophilic attack, a precipitate forms. This precipitate is
dinitrophenylhydrazone. If a red dinitrophenylhydrazone forms then
the aldehyde or ketone is aromatic if not, the dinitrophenylhydrazone
is yellow. Acetone, cyclohexanone, formaldehyde, and benzaldehyde
should form yellow precipitates.
Experimental When 2,4-Dinitrophenylhydrazine was added to the samples, the
Results / Observations following changes happened:
 Acetone produced a yellow orange solution with fine
precipitates.
 Cyclohexanone produced a yellow solution with fine yellow
precipitates.
 Formaldehyde produced a yellow solution with fine
precipitates.
 Benzaldehyde produced a yellow orange solution with large
yellow precipitates.
 Acetic acid produced a yellow solution
 Ethanol produced a yellow solution
Inference Acetone, cyclohexanone, formaldehyde, and benzaldehyde are
aldehydes and ketones.
Acetic acid and ethanol are not aldehydes and ketones.

Schiff’s test for Aldehydes

Procedure The samples used were acetone, formaldehyde, cyclohexanone, and
benzaldehyde which are colorless liquids.
Schiff’s reagent is a green pink solution.
4 drops or 50 mg of sample was added to 1 mL of Schiff’s reagent.
 13

Reaction Involved

Expected Results Schiff’s reagent only reacts with aldehydes. When aldehydes react
with the Schiff’s reagent, a bright purple product is formed.
Formaldehyde and benzaldehyde should form a bright purple product.
Experimental When 1 mL Schiff’s reagent was added to the samples, the following
Results / Observations happened:
 Acetone did not react since there was no change observed in
the solution
 Formaldehyde produced a yellow solution which turned
purple.
 Benzaldehyde produced a yellow solution which became pale
yellow with pink precipitates and an immiscible pink top layer.
Inference Formaldehyde and benzaldehyde have aldehyde functional group.

Tollen’s test for Aldehydes

Procedure The samples used were acetone, formaldehyde, cyclohexanone, and
benzaldehyde which are colorless liquids.
Tollen’s reagent is a colorless solution with white suspended particles.
4 or 50 mg of sample was added to Tollen’s reagent in a test tube.
When no reaction occurred, the test tube was heated until 60oC.
Reaction Involved

Expected Results When Tollen’s reagent is reacted with an aldehyde, the Tollen’s
 14

reagent is reduced to silver metal which is indicated by the formation

of a metallic black precipitate. Formaldehyde and benzaldehyde
should form metallic black precipitates.
Experimental When Tollen’s reagent was added to the sample, the following
Results / Observations changes happened:
 Acetone produced a black solution with a solid and
precipitates.
 Formaldehyde produced a dark green solution with
precipitates.
 Cyclohexanone produced a black solution with precipitates.
 Benzaldehyde formed a black solution with a solid and
precipitates.
Inference Impurities in the reagents or samples have altered the result to be less
accurate which made cyclohexanone and acetone precipitate silver
metal. The aldehydes should be benzaldehyde and formaldehyde.

Fehling’s test for Distinguishing Aromatic from Aliphatic Aldehydes

Procedure The samples used were acetone, formaldehyde, cyclohexanone,
benzaldehyde, and glucose (dissolved in water) which are colorless
liquids.
Fehling’s solutions A and B form a dark blue solution.
1 mL of each Fehling’s solution A and B were mixed to create a dark
blue solution then it was mixed with 4 drops or 50 mg of sample then
the test tube was heated by a water bath.
Reaction Involved RCHO + 2Cu2+ + 2H2O ==> RCOOH + Cu2O + 4H+
Expected Results Only aldehydes react with Fehlings solution to reduce copper (II) to
copper (I). The reduction reaction is indicated by the formation of
brown or brick red precipitates which are insoluble Cu2O.
Formaldehyde, benzaldehyde, and glucose should produce brick red
precipitates.
Experimental The following happened when 4 drops of sample was added to 2
Results / Observations drops each of Fehling’s solution A and B:
 Acetone produced a transparent blue solution.
 Cyclohexanone produced two immiscible layers: a clear top
layer and a transparent blue bottom layer.
 Formaldehyde produced a transparent blue solution.
 Benzaldehyde produced a milky blue solution with bubbles on
the surface .
 Glucose produced a transparent blue solution.
The following happened when the solution containing Fehling’s
solution A and B and the sample are heated:
 Acetone remained transparent blue
 Cyclohexanone remained having two immiscible layers: a clear
top layer and a transparent blue bottom layer.
 15

 Formaldehyde produced a blue green solution with brown

orange precipitates.
 Benzaldehyde remained milky blue but with green yellow
precipitates.
 Glucose remained transparent blue but with red violet
precipitates.
Inference Formaldehyde, benzaldehyde, and glucose formed precipitates so they
have aldehyde functional group.

Reaction with Sodium Bisulfite for Aldehydes and Aliphatic methyl Ketone
Procedure The samples used were acetone, formaldehyde, cyclohexanone, and
benzaldehyde which are colorless liquids.
Sodium Bisulfite is a colorless liquid.
4 drops or 50 mg of sample was added to 1 mL sodium bisulfite
solution then it was shaken. It was left to stand for 2 minutes.
Reaction Involved

Expected Results When a ketone reacts with sodium bisulfite, a precipitate is formed. If
the ketone is a methyl ketone, no precipitate is formed. This means
that only cyclohexanone should form a precipitate.
Experimental When sodium bisulfite was added to the samples, the following
Results / Observations happened:
 Acetone did not react since no changes were observed.
 Benzaldehyde produced two immiscible layers.
 Cyclohexanone temporarily produced an oily cloudy white
solution then it separated into two immiscible layers.
 Formaldehyde did not react since no changes were observed.
Inference Cyclohexanone is a ketone but not a methyl ketone.

Chromic Acid test for Aldehydes

Procedure The samples used were acetone, formaldehyde, cyclohexanone, and
benzaldehyde which are colorless liquids.
Chromic acid is a dark yellow solution.
1 mL of acetone was added to 2 drops or 25 mg of sample and 5 drops
of chromic acid.
 16

Reaction Involved

Expected Results When chromic acid oxidizes, it turns into a green solution.
Chromic acid oxidizes in aldehydes faster compared to ketones.
Banzaldehyde and formaldehyde will form a green solution faster than
acetone and cyclohexanone.
Experimental The following happened when chromic acid and acetone was added to
Results / Observations the samples:
 Acetone did not react since no changes were observed.
 Benzaldehyde produced a dark brown (coffee-like) solution
and it released heat (exothermic).
 Cyclohexanone produced two immiscible layers: an orange top
layer and a black bottom layer.
 Formaldehyde produced a dark brown solution and it released
heat (exothermic).
Inference Benzaldehyde and Formaldehyde are aldehydes while Cyclohexanone
and acetone are ketones.

Carboxylic acid & Acid derivatives

Oxidation with Potassium Permanganate
Procedure The samples used are acetic acid, lactic acid, benzoic acid, and
succinic acid. Acetic acid and lactic acid are colorless liquids. Benzoic
acid is a white crystalline solid so it was dissolved in ethanol. Succinic
acid is a white crystalline solid so it was dissolved in water.
1% potassium permanganate is a purple solution.
5 drops of sample was added to 5 mL 1% potassium permanganate
solution then the mixture was heated using a water bath.
Reaction Involved
Expected Results
Experimental After adding 1% potassium permanganate solution and heating in a
Results / Observations water bath, the following changes happened:
 Acetic acid did not react since no change was observed
 Lactic acid produced a clear brown solution with brown
precipitates.
 Benzoic acid produced a dark chocolate brown solution.
 Succinic acid produced a light chocolate brown solution.
Inference
 17

Esterification
Procedure The sample used is salicylic acid which is a white crystalline solid.
Methanol and sulfuric acid are colorless liquids.
50 mg salicylic acid was placed in a test tube then, 2 mL of methanol
and 10 drops of concentrated sulfuric acid was added. The mixture
was heated using a water bath then cooled to room temperature.
Reaction Involved

Expected Results When salicylic acid is reacted with excess methanol, the carbonyl
group in salicylic acid becomes more electrophilic. This makes it bond
to another hydrocarbon group thus creating an ester. The presence of
an ester is indicated by a fruity odor. The final product of the
esterification should smell fruity.
Experimental When methanol and sulfuric acid was added to salicylic acid and after
Results / Observations heating and cooling the solution in a water bath, the solution produced
was odorless and was forming bubbles.
Inference The final product should smell fruity but due to personal errors the
odor was not able to be observed.

Salt formation
Procedure The samples used are acetic acid, lactic acid, benzoic acid, and
succinic acid. Acetic acid and lactic acid are colorless liquids. Benzoic
acid is a white crystalline solid so it was dissolved in ethanol. Succinic
acid is a white crystalline solid so it was dissolved in water.
Zinc metal is a gray and fine powder.
A pea size of zinc metal was added to a test tube containing 1 mL of
sample.
Reaction Involved
Expected Results
Experimental When Zinc metal was added to the sample, the following changes
Results / Observations happened:
 Fine zinc metal separated from acetic acid. Bubbles formed at
the surface of the zinc metal and some zinc metal stocked to
the walls of the test tube.
 Zinc metal did not separate from lactic acid. The mixture
produced was viscous liquid. Gray wet crystals formed at the
sides of the test tube and bubbles formed at the surface of the
mixture.
 Fine zinc metal settled and formed a circle. It separated from
Benzoic acid.
 18

 Granulated zinc metal formed and separated from succinic acid

and bubbles formed at the surface of the zinc metal.
Inference

Schotten-Bauman Reaction: Formation of Ester from Acyl Halide and

Alcohols
Procedure Ethyl alcohol and 20% sodium hydroxide are colorless liquids.
Benzoyl chloride is a colorless to light yellow liquid.
1 mL of ethyl alcohol and 2 mL of water was mixed in a test tube. 5 drops of
benzoyl chloride was added to the mixture while shaking then 3 mL of 20%
sodium hydroxide was also added.
Reaction
Involved

Expected Acyl halides react with alcohols in basic condition to form an ester which is
Results immiscible in water and less dense than water. The formation of an ester using
benzoyl chloride, an acyl halide, and ethyl alcohol with sodium hydroxide is
indicated by the formation of an immiscible layer and a sweet odor.
Experimenta After shaking and adding ethyl alcohol, 20% sodium hydroxide, and benzoyl
l Results / chloride, the solution turned viscous with tiny bubbles. After a few minutes, it
Observations formed two immiscible clear layers. The odor of the mixture was sweet and
minty.
Inference An ester was formed by reacting benzoyl chloride, an acyl halide, and ethyl
alcohol with sodium hydroxide.

Alkaline Iron (III) Hydroxamate test for Carboxylic Acid

Procedure Ethyl acetate, hydroxylamine hydrochloride in ethanol, and sodium
chloride are colorless liquids.
10% Iron (III) chloride is a green black solution.
2-3 drops of ethyl acetate was added to 1 mL of 5% hydroxylamine
hydrochloride in ethanol then, 4 drops of 5% sodium chloride solution
was added and the mixture was heated to boiling using a water bath.
When the test tube cooled, 2 mL of 1M hydrochloric acid was added.
When cloudliness develops, add 2 mL of ethanol. After, 10% iron (III)
chloride was added dropwise while swirling.
Reaction Involved

Expected Results When esters react with hydroxylamine in basic solution, it forms
 19

hydroxamic acid that will react to ferric chloride which will form
bluish red hydroxamates. In using ethyl acetate, the product formed
should be bluish red in color.
Experimental When ethyl acetate, hydroxylamine hydrochloride in ethanol, and
Results / Observations sodium chloride solution were mixed and heated, the solution
produced was colorless.
When 10% Iron (III) chloride was added, the solution produced was
yellow and it had an oily dispersed appearance.
No ethanol was added since the solution was not cloudy after cooling.
Inference Impurities in the reagents or samples have altered the result to be less
accurate which diluted the product formed. Ethyl acetate is an ester.

Amines
Basicity of Amines
Procedure The solutions used were methylamine, diethylamine, triethylamine,
and aniline. Methylamine is a colorless liquid. Diethylamine is a dark
orange liquid. Triethylamine is a light yellow liquid. Aniline is a dark
brown liquid.
Phenolphthalein is a colorless liquid.
Bromothymol blue is a blue liquid.
2 drops or 25 mg of sample was added to each two test tubes. One test
tube was added with 1 drop of phenolphthalein and the other test tube
was added with 1 drop of bromothymol blue.
Reaction Involved
Expected Results
Experimental When phenolphthalein was added to the samples, the following
Results / Observations happened:
 Methylamine changed from clear to a purple solution.
 Diethylamine did not react since no change was observed.
 Triethylamine
 Aniline changed form an oily red solution to an oily red brown
solution.
When bromothymol blue was added to the samples, the following
happened:
 Methylamine changed from clear to a dark blue solution.
 Diethylamine changed form a yellow to a dark blue solution.
 Triethylamine changed from a clear to a dark blue solution
with emulsions at the sides.
 Aniline changed form an oily red solution to a blue solution
with oily brown red emulsions at the surface.
Inference
 20

Salt formation
Procedure The samples used were methylamine, diethylamine, triethylamine,
and aniline. Methylamine is a colorless liquid. Diethylamine is a dark
orange liquid. Triethylamine is a light yellow liquid. Aniline is a dark
brown liquid.
Hydrochloric acid is a colorless liquid.
1 mL of concentrated hydrochloric acid was added with 5 drops of
sample. After, the mixture was cooled using a cold water bath then 2
mL of distilled water was added to the resulting mixture.
Reaction Involved
R - NH2 + HCI —→  RNH3 CI            
                              Alkylammonium
                                 Chloride
 

Expected Results
Experimental When hydrochloric acid was added to the samples, the following
Results / Observations changes were observed:
 Methylamine produced a colorless liquid.
 Diethylamine produced a cloudy light orange solution.
 Triethylamine produced two immiscible layers: the top layer
was cloudy white and the bottom layer was colorless.
 Aniline produced a cloudy white solution with red
coagulations.
When the samples with hydrochloric acid were cooled, the following
changes were observed:
 Methylamine did not change.
 Diethylamine did not change.
 Triethylamine did not change.
 Aniline became a white solution with red coagulations.
When distilled water was added to the samples, the following changes
were observed:
 Methylamine did not change.
 Diethylamine became a lighter orange solution (diluted).
 Triethylamine still had two immiscible layers but with some
changes: the top layer became whiter and the bottom layer was
added.
 Aniline became a colorless solution with red coagulations.
Inference
 21

Effect of Amino group in substitution in the Benzene ring

Procedure The sample used is aniline which is a dark brown liquid.
Bromine water is a yellow brown solution.
3 drops of aniline and 2 mL of water were mixed inside a test tube
then, bromine water was added dropwise.
Reaction Involved
Expected Results
Experimental When water and bromine water was added to aniline, a clear solution
Results / Observations was formed with brown bubbles then it became a cloudy white
solution with dark brown bubbles and a light brown big bubble in the
middle of the solution. Fumes evolved.
Inference

Oxidation of Aniline with Potassium Permanganate

Procedure The samples used were methylamine, diethylamine, triethylamine, and
aniline. Methylamine is a colorless liquid. Diethylamine is a dark
orange liquid. Triethylamine is a light yellow liquid. Aniline is a dark
brown liquid.
1% potassium permanganate is a purple solution.
In 4 drops or 50 mg of sample, 1 mL of water and 1% potassium
permanganate solution was added. After, the mixture was shaken.
Reaction Involved
Expected Results
Experimental When water and 1% potassium permanganate solution was added to
Results / Observations the samples, the following were observed:
 Methylamine produced a colorless solution which turned into a
light brown solution with brown precipitates.
 Diethylamine produced a dark orange solution then formed
brown precipitates.
 Triethylamine produced a light yellow solution with two
immiscible layers: the top layer was cloudy white and the
bottom layer was dark brown.
 Aniline produced an amber solution which turned into a dark
brown solution with brown precipitates.
Inference

Quinhydrone test
Procedure The samples used were methylamine, diethylamine, triethylamine,
and aniline. Methylamine is a colorless liquid. Diethylamine is a dark
orange liquid. Triethylamine is a light yellow liquid. Aniline is a dark
brown liquid.
Quinhydrone is a green solution.
2 drops or 25 mg of sample was added to 6 mL of water in a test tube.
 22

After, a drop of 5% Quinhydrone in methanol solution was added then

the mixture was shaken and left standing for 2 minutes.
Reaction Involved
Expected Results
Experimental When water was added to the samples, the following were observed:
Results / Observations  Methylamine dissolved.
 Diethylamine dissolved.
 Triethylamine dissolved.
 Aniline did not dissolve and formed brown oily balls.
When quinhydrone solution was added to the samples, the following
were observed:
 Methylamine produced a colorless solution which turned
purple.
 Diethylamine produced a colorless solution which turned light
brown.
 Triethylamine produced a colorless solution which turned
medium brown.
 Aniline produced a colorless solution which turned dark
brown.
Inference

http://www2.ucdsb.on.ca/tiss/stretton/CHEM2/orglab1.htm

http://www.tutorvista.com/content/chemistry/chemistry-iii/hydrocarbons/alkynes-chemical-
properties.php

http://www.docbrown.info/page04/OilProducts05.htm

http://www.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/ClassificationTests/uns
aturation.html#Bromine

http://faculty.swosu.edu/william.kelly/pdf/qo4.pdf

http://www.docbrown.info/page13/ChemicalTests/ChemicalTestsf.htm

http://phoenix.liu.edu/~nmatsuna/che122/exp13.pdf

http://www.chemguide.co.uk/organicprops/phenol/ring.html

http://www.chemistry.ccsu.edu/glagovich/teaching/316/qualanal/tests/ceric.html

http://www.wsc.ma.edu/cmasi/organic_lab/organic1_lab/esterification_salicylic_acid.pdf