Purpose of experiment:

This experiment was carried out to determine the identities of five colourless solutions to

which labels were given to match to each individual bottle. The method of qualitative analysis

was used to identify the solutions using simple tests involving reagents that were provided.

Variables:

Independent variable Method of application

Colourless solutions of unknown identity. The condition and appearance of the unkown
colourless solutions were noted before adding
reagents to identify them.

Dependent variable Response of method

Reagent added to identify solution. Observation of physical changes were
recorded after addition of reagents.

Controlled variables Method of controlling

Volume of unknown colourless solution
added to test tube.
Amount of reagent added to unknown
colourless solution.
The volume of unknown colourless solution
added to each test tube was kept constant at
2cm depth.
3-4 drops of reagent were added to each test
tube containing the unknown colourless
solution.
 Introduction:

The method of qualtitative analysis was carried out in this experiment to determine the

identity of five colourless solutions in which the labels have fallen off. Reagents were provided

to aid in the investigation. Tollen’s reagent, sodium bicarbonate powder and acidified potassium

permanganate were the reagents given. The labels which dropped off had written on them

ethanol, 2-methyl-2-propanol, ethanal, propanone and acetic acid. All of which are classified

under organic compounds.

Background theory:

Ethanol and 2-Methyl-propanol are both categeorized as alcohol group species. The

difference between the two is that ethanol is a primary alcohol whereas 2-Methyl-propanol is a

tertiary alcohol. Generally, alchohols are compounds in which one or more hydrogen atoms in an

alkane have been replaced by an –OH group. Primary (1°) alcohols, the carbon which carries the

–OH group has only one alkyl group attached to it. For example:

𝐶𝐻3 − 𝐶𝐻2 − 𝑂𝐻

Ethanol

Tertiary alcohols however, have three alkyl groups attached to the carbon carrying the –OH

group. As shown in 2-Methyl-propanol :

In order to differentiate between the two, we used the acidified potassium permanganate, KmnO4

which was provided to oxidize the alcohols. When added to ethanol which is a primary (1°)

alcohol, a colour change from purple to brown is observed. The colour change can be attributed

to the reduction of Mn7+ to Mn2+ in acidic condition. Partial oxidation occurs where an aldehyde

is formed. This outcome can only be achieved with excess amount of primary (1°) alcohol added.

The excess of alcohol means that there isn’t enough oxidizing agent present to carry out the

second stage of oxidization so an aldehyde and water are produced.

Tertiary alcohols have no reaction when acidified potassium permanganate is added. This

happens due to the lack of hydrogen atom attached to the carbon linked to the –OH group. In a

primary alcohol, the oxidizing agent is removing the hydrogen from the carbon atom attached to

the –OH group. The lack of which in a tertiary alcohol results in no reaction occuring.

*There is no hydrogen attached to the carbon for the oxygen to remove.

To further conclude the findings and observations recorded, tollen’s reagent is added to both the

ethanol and 2-Methyl-propanol after being oxidized by the acidified potassium permanganate.

The primary (1°) alcohol would produce an aldehyde which will undergo a visible colour change

from brown to grey with precipitate. An aldehyde is a simple compound which contains a
carbonyl group (a carbon-oxygen double bond) that has a hydrogen atom attached to it with

either a second hydrogen atom or a hydrocarbon group like an alkyl. An example would be

ethanal which is one of the labels fallen off.

Tollens' reagent contains the diamminesilver(I) ion, [Ag(NH3)2]+. Diamminesilver(I) ion is

reduced by aldehyde to produce metallic silver which results in the grey precipitate produced.

𝐴𝑔(𝑁𝐻3 )2 + 𝑒 − → 𝐴𝑔 + 2𝑁𝐻3

𝑅𝐶𝐻𝑂 + 3𝑂𝐻 − → 𝑅𝐶𝑂𝑂− + 2𝐻2 𝑂 + 2𝑒 −

2𝐴𝑔(𝑁𝐻3 )+ −
2 + 𝑅𝐶𝐻𝑂 → 2𝐴𝑔 + 𝑅𝐶𝑂𝑂 + 4𝑁𝐻3 + 2𝐻2 𝑂

Tertiary alcohol in this case would not react with tollen’s reagent having unable to be oxidized

by acidified potassium permanganate.

Moving on, one of the fallen labels had acetic acid written on it. Acetic acid can be grouped

under the organic compound branch of carboxylic acids. A carboxylic acid is a compound which

contains a –COOH group which is attached either to a hydrogen atom or to an alkyl group.
 *ethanoic acid is also known as acetic acid.

To identify which one of the five unkown colourless solutions is acetic acid, sodium carbonate is

used. Theoretically, when a metal carbonate is added to a carboxylic acid; carbon dioxide, CO2

gas is formed which is physically visibe through a brisk effervesence.

𝐶𝐻3 𝐶𝑂𝑂𝐻 + 𝑁𝑎𝐻𝐶𝑂3 → 𝐶𝐻3 𝐶𝑂𝑂𝑁𝑎 + 𝐻2 𝑂 + 𝐶𝑂2

Propanone is classified under the organic compound group of ketones. Ketones are carbonyl

group compounds that have two hydrocarbon groups attached to it. They never have hydrogen

atoms attached to the carbonyl group which makes it distinct from aldehydes.

Aldehydes and ketones being nearly similar having carbonyl groups are distinguishable via the

addition of Tollen’s reagent as mentioned above. Ketones do not have any hydrogen atom

attached to the carbonyl group making it unable to be oxidised by tollen’s reagent.

 Materials and apparatus:

Materials  Five colourless solutions of unkown

identity.
 Tollen’s reagent.
 Sodium Carbonate powder.
 Acidified potassium permanganate,
KMnO4.
Apparatus  Test tubes.
 Test tube rack.
 Liquid droppers.
 250ml beaker.
 Tripod stand.
 Wire gauze.
 Bunsen burner.
 Gas lighter.
 Labelling stickers.
 Spatula.
 Experimental procedures:

1. A sample of each one of the five unknown colourless solutions is put into five test tubes

labelled A, B, C and D accordingly up to 2cm depth.

2. A warm water bath is set up using a beaker half-filled with water placed on top of a

tripod stand with wire gauze which is then heated with a bunsen burner.

3. Three drops of tollen’s reagent were then added to test tubes labelled from A to D.

4. After that, all of the test tubes were put into the warm water bath to speed up the rate of

reaction.

5. Any changes in physical appearance and reactions were then recorded down.

6. Steps 1 to 5 were repeated using different reagents.

7. The recorded observations were then tabulated.

 Safety precautions:
Hazard
1.Usage of bunsen burner.
2.Warming/heating of substances.
3.Handling of apparatus.
Safety precaution
 Ensure that the lighter or match is lit
before opening the gas valve of the
bunsen burner to prevent injuries.
 Place the bunsen burner on a stable
surface to prevent it from toppling and
becoming a fire hazard.
 Make sure that no flammable
substances come in contact with the
open flame of the bunsen burner.
 Goggles are to be worn at all times
when heating/warming chemical
substances to prevent injury to eyes.
 A mask is to be worn when
heating/warming chemicals to prevent
inhalation of harmful gaseous
products.
 Ensure that all glass apparatus are
handled with care to prevent injury
due to broken sharp glass.
 Covered shoes are to be worn at all
times when in the lab to prevent injury
from falling apparatus.
 Observations and results:

Raw data

Sample. Tollen’s reagent. Sodium Acidified Addition of

bicarbonate. Potassium tollen’s
Permanganate. reagent after
acidified
KMnO4
A - - - -
B Light brown - - -
C Grey solution - Brown solution Grey
precipitate
D White fumes Brisk - -
effervesence
E Grey precipitate - - -

Analysis of data

Based on the observations recorded above, Sample C is determined to be the primary

alcohol, ethanol since it reacts with acidified potassium permanganate to produce a colour

change from purple to brown. The resulting brown solution formed an aldehyde as the alcohol

was oxidised. Tollen’s reagent was then added to the mixture and a grey precipitate was formed.

The grey precipitate formed was in fact silver metal as a result of the Diamminesilver(I) ion

being oxidised by the aldehyde produced. When Sodium bicarbonate was added to D, it

produced a brisk effervesence which was not observed in the other four samples. This

observation is in line with the reaction of metal carbonates with acids where in which carbon

dioxide gas is produced. Sample D can be then said to be acetic acid. Finally, the last sample E

reacted with tollen’s reagent to produce a grey precipitate which then confirmed it to be the

aldehyde propanal.
 Lastly, the remaining two labels are that of ketone and tertiary alcohol species. The

challenging part arises when both of the samples do not exhibit any significant chemical reaction

that differs them from each other when tested with all three available reagents. A suggestion

would be to use 2,4-dinitrophenylhydrazine in order to differentiate the two remaining samples

of A and B. If the sample were to be a ketone, a few drops of 2,4-dinitrophenylhydrazine would

yield an observation of a bright orange or yellow precipitate. The test is mainly to prove the

existence of a carbon-oxygen double bond.

When added to tertiary alcohols, a similar condensation reaction occurs but no visible

colour change is observed.

The findings of the experiment can be summarized into a table as shown below:

Sample Label
C Ethanol
D Acetic acid
E Propanal
Discussion:

1. The concentration of the unkown colourless solutions may have been too low to

observe a silver mirror when tollen’s reagent was added and the test tube was left

in a warm water bath. Hence, grey precipitate was observed instead.

2.
 Reference list:

Clark, J. (2004) ADDITION-ELIMINATION REACTIONS OF ALDEHYDES AND KETONES

Available at: https://www.chemguide.co.uk/organicprops/carbonyls/addelim.html (Accessed:26

March 2018)

Clark, J. (2003) INTRODUCING ALCOHOLS Available at:

https://www.chemguide.co.uk/organicprops/alcohols/background.html (Accessed:26 march

2018)

James (2018) 1°, 2°, 3°, 4° Available at:

https://www.masterorganicchemistry.com/2010/06/16/1%C2%B0-2%C2%B0-3%C2%B0-

4%C2%B0/ (Accessed:26 march 2018)