Identification of an Unknown Organic Compound

Mark Riley

Task Practical report

Introduction An organic compound is any member of a large class of chemical compounds whose molecules
contain carbon with exception of a few types of compounds such as carbonates, carbides and
cyanides. One or more of the carbon atoms are often covalently linked to atoms of other
elements, most commonly hydrogen, oxygen, or nitrogen. Organic compounds are found in
nature but can also be synthesized in the laboratory. We encounter so many organic compounds
everyday, such as when we use perfumes or even drink a glass of alcohol. Each organic
compound belongs to a particular chemical family and this experiment will investigate aldehydes,
ketones, alkyl halides, carboxylic acids and alcohols- culminating in an evaluation of to which
family an unknown organic sample belongs to.

Aim To identify an unknown organic compound using a pre-prepared flow chart.

Hypothesis By following the prepared flow chart, the unknown organic sample will be correctly identified.
(Provided that steps & procedures are followed as carefully and accurately as possible)

Method 1. Follow the procedures in the series of tests outlined on the flow chart.
2. Using the results, determine the nature of the unknown organic compound.
3. Knowing the nature of the unknown compound, determine (even if by elimination) the family
to which the unknown sample belongs.
4. Use confirmation tests to confirm these results.
5. If there is more than one organic compound listed that belongs to this same family, conduct
further experimentation using boiling points or density to identify the compound.

(refer to flow chart and pages 5-9)

Mark Riley 3107631608 I dentification of an Unknown Organic 1

Equipment

 Safety glasses
 Lab coat
 Rubber gloves
 Test tubes
 Blue litmus paper
 Dropping pipettes
 Bulb pipette
 250mL beaker
 Digital scales
 Test tube rack
 Bunsen burner
 Heating mantle or oil bath
 Reflux apparatus
 Thermometer
 Heat resistant mat
 Tripod
 Gauze
 Retort stand
 Clamp
 Chemicals-
o 1M H2SO4 (Sulphuric acid)
o 0.1M K2Cr2O7 (Potassium dichromate)
o 0.1M AgNO3 (Silver nitrate)
o 2M NH3 (Ammonia)
o NaHCO3 (Sodium bicarbonate)
o 2-butanol
o Sodium metal
o 2-methyl-2-propanol
o Ethanol
o KOH (potassium hydroxide)
o 2M HNO3 (Nitric acid)

Safety Precautions

 Some of the chemicals being used are considered to be toxic and gloves as well as safety glasses should
be worn throughout the experiment.
 Check that the eye wash basin is functioning correctly before starting the experiment.
 A pathway to the wash and eye wash basin should be clear at all times.
 A chemical & flame retardant protective lab coat should be worn during the experiment.
 Fully covered shoes must be worn.
 Work benches should be kept clear and used equipment should be rinsed after use.
 All chemicals being used should be clearly labeled.
 Chemicals are flammable so open containers must be kept away from flames.
 Much care should be taken when using sodium as it is very reactive.

Mark Riley 3107631608 I dentification of an Unknown Organic 2

 Organic 2-methyl-2-
1-propanol 1-butanol 2-butanol dichloromethane
Compound propanol
Chemical Alcohol Alcohol
Alcohol Secondary Alcohol Tertiary Alkyl Halide
Family Primary Primary
Chemical
C3 H8 O C4 H10 O C4 H10 O C4 H10 O Cl2 H2 C
Formula

Structure

CONFIRMATION TESTS Use density wherever possible

Boiling point 97.4°C (96-98) 118°C (116-120) 99.5°C (99-101) 82.3°C (81-83) 61.7°C (96-98)
𝐺𝑟𝑎𝑚𝑠 𝐺𝑟𝑎𝑚𝑠 𝐺𝑟𝑎𝑚𝑠 𝐺𝑟𝑎𝑚𝑠 𝐺𝑟𝑎𝑚𝑠
Density 𝟏𝟔. 𝟎𝟕 20𝑚𝐿
𝟏𝟔. 𝟐𝟎 20𝑚𝐿
16.14 20𝑚𝐿
𝟏𝟓. 𝟕𝟕 20𝑚𝐿
𝟐𝟔. 𝟒𝟎 20𝑚𝐿

Organic Compound methanal propanone propanoic Acid ethanoic Acid

Chemical Family Aldehyde Ketone Carboxylic Acid Carboxylic Acid

Chemical Formula CH3 O C3 H6 O C3 H6 O2 C2 H4 O2

Structure

CONFIRMATION TESTS Use density wherever possible

Boiling point 100°C 56.1°C (55-58) 141°C (139-142) 117.9°C (116-119)

𝐺𝑟𝑎𝑚𝑠 𝐺𝑟𝑎𝑚𝑠 𝐺𝑟𝑎𝑚𝑠 𝐺𝑟𝑎𝑚𝑠
Density 𝟐𝟏. 𝟓𝟔 20𝑚𝐿
𝟏𝟓. 𝟕𝟎 20𝑚𝐿
𝟏𝟗. 𝟖𝟔 20𝑚𝐿
𝟐𝟎. 𝟗𝟖 20𝑚𝐿

Mark Riley 3107631608 I dentification of an Unknown Organic 3

 THIS
BLANK
PAGE
IS
WHERE
THE
FLOWCHART
GOES

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 TEST 1.

Test Number 1

Equipment •Test tube •Test tube rack •Distilled water •Dropper •Blue litmus paper

1. Add a few drops of distilled water into a test tube along with 10 drops of the unknown organic
Procedure sample.
(also see flow chart)
2. Test the mixture using blue litmus paper.

The unknown sample and the water were miscible. The solution remained colourless and transparent. The
Observations
litmus paper did not undergo any colour change.

Blue litmus paper will turn red if [H+] present which identifies a solution as acidic. From the organic
compounds listed, only carboxylic acid will ionize to any extent (H-atom attached to the –OH group).

Discussion
The litmus paper did not undergo any colour change and remained blue indicating the unknown solution
was not acidic, thus eliminating carboxylic acid as a possible family to which the unknown sample could
belong to.

Families &
The carboxylic acid family of organic compounds have been eliminated which include propanoic acid and
compounds
ethanoic acid.
eliminated
Alkyl halides Dichloromethane
Primary alcohols 1-propanol, 1-butanol
Remaining Secondary alcohols 2-butanol
possibilities Tertiary alcohols 2-methyl-2-propanol
Aldehydes Methanal
Ketones Propanone

Mark Riley 3107631608 I dentification of an Unknown Organic 5

 TEST 2.

Test Number 2

•Test tube •Test tube rack •1M H2SO4 sulphuric acid •0.1M K2Cr2O7 potassium dichromate
Equipment
•Dropper

1. Place 10 drops of the unknown substance into a test tube.

Procedure 2. Add 20 drops of 1M H2SO4 sulphuric acid into the test tube.
3. Add 5 drops of K2Cr2O7 potassium dichromate

Observations The solution was miscible and orange. The solution remained orange and no noticeable reaction occurred.

K2Cr2O7 potassium dichromate is easily reduced & works as a mild oxidant. K2Cr2O7 is orange & when
reduced (𝐶𝑟 6+ → 𝐶𝑟 3+) it turns green. When a reactant is reduced another reactant has been oxidized.
The only organic compounds listed that can be oxidised are as follows-

Primary Alcohol OXID→ Aldehyde Aldehyde OXID→ Carboxylic acid Secondary Alcohol OXID→ Ketone
Discussion
A positive test (orange to green) therefore indicates that one of the substances underlined above is
present. A carboxylic acid can be oxidized to CO2 + H2O but this is with much difficulty and for the purpose
of this experiment will be ignored. In this test the solution remained orange, so there must not have been
any primary alcohols, secondary alcohols or aldehydes present. Therefore all three ofthese can be
eliminated as possibly being the unknown organic sample.

Families & Primary alcohols have been eliminated which include 1-propanol and 1-butanol. 2-butanol is no longer a
compounds possibility either as all secondary alcohols have been eliminated. Methanol is from the aldehyde family
eliminated which has also been eliminated.

Alkyl halides Dichloromethane

Remaining
possibilities Tertiary alcohols 2-methyl-2-propanol
Ketones Propanone

Mark Riley 3107631608 I dentification of an Unknown Organic 6

 TEST 4.

Test Number 3

Equipment •Test tube •Test tube rack •Sodium metal •Dropper

1. Add 5 drops of the unknown organic sample to a clean DRY test tube.
Procedure
2. Carefully add a small piece of sodium metal to the test tube.

There was no visible reaction. The sodium metal stayed in a solid state and underwent no transformation.
Observations
The unknown sample remained colourless and transparent.

Just as sodium reacts with water to liberate hydrogen gas so too does sodium liberate hydrogen from
alcohols or carboxylic acids. A positive test (fizzing as the hydrogen gas is released) indicates that the
substance is either a carboxylic acid or an alcohol. Because no reaction happened when the sodium metal
Discussion
was added to the unknown organic sample, it can now be deduced that the organic sample is not a tertiary
alcohol. This test has also further proved the results from the previous tests that had already eliminated
primary alcohols, secondary alcohols and carboxylic acids as being the unknown organic sample.

Families &
2-methyl-2-propanol is a tertiary alcohol and the possibility that the unknown organic sample may be a
compounds
tertiary alcohol has now also been eliminated.
eliminated
Remaining Alkyl halides Dichloromethane
possibilities Ketones Propanone

Mark Riley 3107631608 I dentification of an Unknown Organic 7

 TEST 5.

Test Number 4

•Test tube •Test tube rack •Dropper •0.1M AgNO3 silver nitrate solution •Ethanol •Potassium
Equipment
hydroxide solid KOH •2M HNO3 Nitric acid •Blue litmus paper

1. Add 6 drops of the unknown organic sample into a mixture of 12 drops of ethanol with a little solid
KOH potassium hydroxide (the ethanol helped dissolve the KOH)
Procedure
2. Cool mixture & add 2M HNO3 (nitric acid) until blue litmus paper turns red indicating solution is
(Alkyl halide test)
acidic.
3. Add 7 drops of AgNO3 (silver nitrate) solution.

The potassium hydroxide was added to the solution and reacted instantly. The solution heated up and
bubbled as gas was released. After the potassium hydroxide had completely dissolved, the solution was
Observations
colourless and miscible. After the solution was made acidic and the AgNO3 silver nitrate solution was added,
a white cloudy precipitate formed.

This is an Alkyl Halide Test and a precipitate forming is a positive indication that the unknown organic
sample is a halo alkane and therefore the unknown organic sample must be dichloromethane. This test
works because hallogens on carbon chains are easily displaced by hydroxide ions. An aqueous solution of
potassium hydroxide is a good source of hydroxide ions. In step 1, the unknown organic sample was added
Discussion
to a hydoroxide solution & the halogen was displaced. The solution is basic so drops of HNO3 Nitric Acid
were added to the solution until it just became acidic. The silver nitrate solution (nitrate because soluble in
almost everything) was then added. (Acid+metal → salt+water). The white cloudy precipitate that formed
was AgCl.

Families &
Propanone has now been ruled out as ketones have been eliminated because the unknown organic
compounds
substance has been found to be an alkyl halide.
eliminated

Mark Riley 3107631608 I dentification of an Unknown Organic 8

CONFIRMATION TEST

Confirmation Test

Equipment •Digital scales •Test tube •50 mL beaker •Bulb pipette

1. Weigh and record the mass of the empty beaker

2. Using the bulb pipette measure 5 mL of the unknown sample
Procedure 3. Add the 5 mL of the unknown sample to the beaker and record the new mass
4. Work out the mass of the 5mL sample of dichloromethane
5. Compare this mass with the expected mass per 1mL (density)

Mass of empty beaker- 𝟐𝟗. 𝟒𝟑 grams

Expected density of dichloroethane per mL- 𝟏. 𝟑𝟐 grams

35.79g − 29.41g = 6.38g per 5mL

Results
6.38g
= 1.28 grams per mL
5mL

1.32 − 1.28 = 0.04

0.04
1.32
× 100 = 𝟑% difference ( very small )

CONFIRMATION TEST IS POSITIVE FOR DICHLOROMETHANE

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 CONCLUSION

The unknown sample was found to be dichloromethane from the functional group
haloalkanes. The hypothesis was correct. By following the pre-prepared flow chart and the
steps and procedures included in it carefully and as accurately as possible, the unknown
organic sample was able to be identified. Flow charts can make identifying unknown
chemicals and compounds a much simpler task.

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