NAMES: Aniskha Punter, Shawn Shaw & Lsaedai Williams

LAB TITLE: Qualitative Organic Analysis DATE:06th/10/2016

PRE-LAB QUESTIONS
1. Why is it important to have clean test tubes before running a test?
Before which tests should acetone not be used to clean the test tubes? [2 mks]
It is important to have clean test tubes before running a test because if the test tubes are
dirty then the experiment may be contaminated and produce wrong results. To prevent
contamination of the solution being used from previous reagents that was in the test tube from
previous experiments.
Acetone should not be used to clean the test tubes before the jones test and the Dinitrophenyl
Hydrazine Test (2,4-DNP Test)

2. Why run solubility tests before running the functional group classification tests? [2
mks]
Solubility tests are run before the functional group classification tests because some functional
groups are soluble while others are not hence by performing a solubility test before the functional
group classification test then the number of functional groups possible are narrowed. Thus time
and materials are saved since the solubility tests help determine the size and polarity of an unknown
compound and the presence of basic or acidic functional groups but not all of the classification
tests are needed to be carried out to identify what functional group is present, only specific ones.
3. Determine the functional group present in these unknown: [4 mks]
(a) Unknown A is soluble in water and gives bubbles with 5% NaHCO3.
Unknown A is a Carboxylic Acid. Carboxylic acids are strong acid so they are able to
react with sodium carbonate and forms carbonic acid and carbon dioxide. The carbonic acid is able
to decompose in water and CO2 forms the bubbles.
(b) Unknown B is insoluble in water, insoluble in 5% NaOH, but soluble in 5% HCl.
Unknown B is an Amine. Because the compound was soluble in 5% HCl, it is most likely an
amine.
(c) Unknown C is insoluble in water, insoluble in 5% NaOH, insoluble in 5% HCl,
soluble with a color change in conc. H2SO4, and decolorizes both KMnO4 (aq) and
bromine in cyclohexane.
Unknown C is an Alkene. It is an Alkene because it was able to react with both the Potassium
Permanganate and Bromine in Cyclohexane after the solubility test.
(d) Unknown D is soluble in water, does not produce bubbles with 5% NaHCO3, gives a
precipitate with 2,4-DNP, and gives a fuchsia color with the Schiff test.

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 Unknown C is an Aldehyde. Schiff reagent reacts only with aldehydes to produce a purple
fuchsia solution.
4. In each of the following cases, describe the next test you would perform. [6 mks]
(a) Unknown X is insoluble in water, 5% NaOH, 5% HCl, and conc. H2SO4.
Because Unknown X is insoluble in water, 5% NaOH, 5% HCl, and conc. H2SO4. There are two
sensible things to do. One is to test for alkyl halide. The Silver Nitrate in Ethanol to Test for 2°
and 3° Alkyl Halides should be performed because the unknown is either an alkyl halide or an
alkane. 1 mL of 2% AgNO3 in ethanol is placed into a test tube where 2 drops of sample is added
and stirred. If a precipitate is formed then that indicates a tertiary, allylic, or benzylic halide.
The other is to Perform the Sodium Iodide in Acetone Test for 1° and 2° Alkyl Halides. 1.0 mL
of Sodium Iodide is placed in acetone into a small test tube where 3 drops of a liquid sample are
added and stirred. The tube stands for 3-6 min at room temperature. If a white precipitate is formed
there is an indication a primary, allylic, or benzylic halide.
(b) Unknown Y is insoluble in water, soluble in 5% NaOH, and insoluble in 5% NaHCO3.
Because Unknown Y is insoluble in water, soluble in 5% NaOH, and insoluble in 5% NaHCO3.
There is an indication that unknown Y may be a phenol hence the next step taken is to perform the
Iron (iii) chloride test to test for phenols. 1 mL of 95% ethanol is placed into a small test tube
where two drops of the test sample and 3-5 drops of 3% FeCl3 are added and mixed. If there is the
presence of bright color, then it indicates the presence of a phenol functional group.
(c) Unknown Z is insoluble in water, insoluble in 5% NaOH, insoluble in 5% HCl, and
soluble in conc. H2SO4.
The substance will either be an alkene, alcohol, an aldehyde or a ketone. Therefore, there are
various test that would be performed: The First test that would be performed is the Bromine in
Cyclohexane and the Potassium Permanganate Test for Alkenes. 1 mL of cyclohexane is placed in
a small test tube where 3 drops of Br2/H2O are added and mixed until the bromine color appears
in the top cyclohexane layer. 2 drops of sample to the Br2/H2O are added and mixed. If a colorless
vicinal dibromide is produced, then that is an indication that unknown z may be an alkene. Alkenes
are oxidized to diols by dilute potassium permanganate (KMnO4), If The purple color of KMnO4
disappears and is replaced by the brown color of manganese dioxide (MnO2) along with a positive
reaction in the Bromine in Cyclohexane test then Unknown Z is an Alkene.
If the substance is not an alkene, then it should be tested to see if it is an alcohol via the TCICA
test. 0.5 mL of the TCICA test solution is placed into a test tube and 1 drop of 5% HCl and sample
is added and mixed. The formation of a precipitate within one min indicates a secondary alcohol;
the formation of a precipitate between 3-20 min indicates a primary alcohol and tertiary alcohols
do not react.
If the substance is not an alcohol either, then it will either be an aldehyde or ketone.1 drop of
sample is added to a test tube and 20 drops of DNP reagent is added and stirred. Aldehydes and
ketones rapidly form yellow, orange, or red precipitates with (DNP) reagent.

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5. You suspect that your unknown contains halogen, so you perform the silver nitrate in
ethanol test and the sodium iodide in acetone test, both of which are negative. Do these
results prove that your compound does not contain a halogen? Briefly explain.
If both the silver nitrate in ethanol test and the sodium iodide in acetone test are negative it DOES
NOT prove that the compound does not contain a halogen because halide ions may not be present
but halogens found in another group. And they are only negative for reactions that can undergo an
SN1 reaction with ethanol or SN2 reaction with acetone. Bromobenzene will not undergo either
reaction, yet still it still will give a negative result, and it contain a halogen.
RESULTS:
TABLE 1: TABLE SHOWING SOLUBLITY FOR BOTH KNOWN AND UNKNOWN
ORGANIC COMPOUNDS

Soluble in:
Name Of
Compound
H2O NaOH NaHCO3 HCl H2SO4

A tick (√) indicates that the compound was soluble in the reagents and an (X) indicates
insolubility