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Qualitative Analysis of Functional Groups

Fatima Latif
SCH4U

Question
The purpose of this lab is to classify unknown organic compounds based
on their functional groups. This will be determined based on their
boiling points, solubility, and reactions to a number of compounds. The
general question: Can we classify organic compounds based on their
boiling points or reactions to other compounds?
Hypothesis
Every organic compound is classified by the functional groups that are
present within the molecule. Functional groups have very distinctive
physical and chemical properties, which will allow us to narrow out
certain possibilities. For instance, compounds that contain a hydroxyl
group can form hydrogen bonds with themselves and with water. For
this reason, they tend to have boiling points higher than compounds that
lack a hydroxyl group, and they tend to be soluble, given that the
number of carbons is relatively small. Distinctions can be made with all
functional groups.
Hypothesis: After performing the experiment, the observations
(solubility, boiling points, reactions to other compounds) can be used to
determine which functional groups are associated with each unknown
compound.
Procedure
1.!

Create a data table with the headings and test column similar to the
one on the website.

2.!

Do the Review Tests first. Click on the test tube icon to

determine what indicates a positive or negative results and the
difference between water soluble and insoluble compounds.
Record your observations in your data table.

3.!

Click each test tube for the 5 unknowns youve been assigned and
record your observations in your data table.

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Observations/Results
Unknown

Water
Solubility

Cerric
Nitrat
e

Chromi
c Acid

DNPH

Iron
Chloride

Iodoform

Review
Test

Testing for
solubility
in
water
(how
many
layers
present
when
mixed with
water)

Testing
for
presenc e
of alcohol
(color
change
from
yellow to
red/redbrown)

Testing
for 1 and
2 alcohols
& aldehyde
s (color
change from
red- orange
to bluegreen)

Testing
for presence
of aldehydes
& ketones
(formation of
yellow/ora
nge/orang
e- red
precipitate
)

Testing for
phenols (color
change from
yellow to
purple/red
dish
brown/gre en

Testing for
acetaldehyd e
and
methyl
ketones
(formation
of yellow
precipitate or
suspension)

Testing for
aldehydes,
alkenes and
phenols (purple
color
disappears)

6
bp>130

Insoluble
two layers
were present

Yes Two
layers,
top layer
was red,
bottom
layer was
yellowbrown

Yes
Color
changed to
blue- green

No
Precipitate
was not
formed

No
Color
remained
yellow

No
Precipitate
was not
formed

No Color
remained
purple

7
bp>110

Insoluble
two layers
were present

No Two
layers,
both
layers
were

No
Color
remained
red- orange

Yes
elloworange
precipitate
was formed

No
Color
remained
yellow

Yes
Yellow
precipitate was
formed

No Color
remained
purple

Potass.
Permang
.

yellow

8
bp>110

Soluble
One layer was
present

Yes One layer,

dark
brown

Yes
Color
changed to
blue- green

No
Precipitate was
not formed

Yes- color
changed to dark
brown/gre en

NoPrecipitate was
not formed

Yes Color
changed from
purple to yellowbrown

9
bp<110

Soluble
One layer was
present

Yes One
layer,
dark red

No
Color
remained redorange

NoPrecipitate was
not formed

No- Color
remained
yellow

NoPrecipitate was
not formed

No- Color
remained
purple

10
bp<110

Soluble

No -

No-

Yes-

No- Color

Yes-

No- Color

One layer was

present

One
layer,
yellow

Color
remained redorange

Yelloworange
precipitate was
formed

remained
yellow

Yellow
precipitate was
formed

remained
purple

Discussion
Polar substances are those that have a net dipole. All hydrocarbons
containing only hydrogen and carbon are non-polar. For a substance to
be polar covalent, it must have a bond that has an electronegativity
difference of 0.5-1.7 and is not counteracted by another polar bond. This
information is important because polar molecules tend to be soluble in
water. Their bond dipoles can attract and break apart the bond dipoles on
water, which is also polar. In other words, most polar molecules are
soluble in water. The first test describes the solubility of the unknown
compounds, by placing them in water and observing how they react. The
compounds that completely dissolved in water are soluble, and in turn
polar. The ones that didnt mix with water and formed two layers are

non- polar. The solubility of substances can be used to infer which

functional groups may or may not be present. For instance, an insoluble
compound may not have a hydroxyl group (alcohol), or if it does, it
could have a very large non-polar hydrocarbon chain that renders it
insoluble.
The second test is the cerric nitrate test. In this, three drops are added to
ten drops of acidified cerric ammonium nitrate solution. This tests the
presence of alcohols, or a hydroxyl group. The cerric ammonium nitrate
solution is initially red, if an alcohol is present, it will react with the
solution and therefore change the color to red or red-brown. In the
reaction, the hydrogen on the hydroxyl group will be removed, and the
oxygen will bond with cerium. Because alcohol can form hydrogen
bonds with each other, they tend to have high boiling points. Thus, if an
alcohol is present, the boiling points can be analyzed and one can
determine the relative length of the chain. For instance, the longer the
hydrocarbon chain, the greater the boiling point. This is due to the
London dispersion forces. Moreover, the longer the chain, the more
likely the compound is insoluble in water.
The third test is the chromic acid test. In this, three drops of the
compound are mixed with 5 drops of acetone and 5 drops of chromic
acid. If a primary or secondary alcohol is present, the solution will
change from red-orange to blue-green. When a primary or secondary
alcohol is in contact with chromic acid, a redox reaction occurs. The
primary alcohol is oxidized to aldehydes and then carboxylic acids, and
secondary alcohols are oxidized to ketones. The chromium is reduced
from +6 to +3. This is what changes the color from red-orange to bluegreen. Tertiary alcohols are not included because they cannot be
oxidized. The carbon that the hydroxyl group is attached too is bonded
to three other carbons. Carbon carbon bonds are too strong to be
broken, therefore it cannot be oxidized.
The fourth test is the DNPH test. It detects the presence of aldehydes or
ketones. Five drops of the compound are mixed with five drops of
dinitrophenylhydrazine in 2ml of ethanol. The carbonyl group on the

aldehyde/ketone reacts with dinitrophenylhydrazine and a condensation

reaction occurs. Water is taken out and a bond is formed between the
two. This causes the formation of a yellow, orange, or orange-red
precipitate.
The fifth test detects the presence of phenols. 20 drops of iron (III)
chloride are added to the unknown compound. If a phenol is present, it
will react with the iron and cause the color to change from yellow to
purple/green/reddish brown. The hydroxyl group on the benzene ring
reacts with the Iron in iron (III) chloride.
The sixth test detects the formation of iodoform, a solid precipitate. If
iodoform is present, then acetaldehyde (methanol) and methyl ketones
are also present in the unknown compound. Three drops of the
compound is added to 3mL of water and 10 drops of KI/I2 solution.
Sodium hydroxide is also added, and the solution is heated at 60 degrees
Celsius. If a methyl ketone or acetaldehyde is present, it will react with
sodium hydroxide and the KI/I2 solution to form a solid precipitate,
chloroform.
The last test involves dissolving three drops of the compound in 2mL of
water or aqueous ethanol. Potassium permanganate is added afterwards.
This evokes a redox reaction if in the presence of an aldehyde, alkene, or
phenol. Aldehydes will be oxidized to carboxylic acids, alkenes will be
oxidized to glycols, and dihydroxyl phenols are oxidized to quinones.
This reaction will cause the purple color of potassium permanganate to
disappear, and slowly form a precipitate of manganese dioxide.
The first unknown compound showed positive results for only the
second and third tests. This means that there is a hydroxyl group, and the
compound can be a primary or secondary alcohol. Because the boiling
point is greater than 130 degrees Celsius, the primary/secondary alcohol
has a chain greater than four carbons long. It can be pentanol, hexanol,
or even a more complex compound.
The second unknown compound showed positive results for the fourth

and sixth tests. The compound is insoluble in water, does not contain an
alcohol, however it does contain an aldehyde or a ketone. This is shown
in the fourth test. The sixth test shows that this compound contains
acetaldehyde or a methyl ketone. Because it showed negative results on
the last test, this compound has a methyl ketone in it and not
acetaldehyde. The compound could not be methanone because it is
insoluble in water. It must be a more complex compound that contains a
methyl ketone in it.
The third unknown compound is soluble, and contains a hydroxyl group.
It also tested positive for the presence of a phenol. Therefore, this
compound is a dihydroxyl phenol (benzene with two hydroxyl groups).
This is known because monohydroxyl phenols do not yield stable
products.
The fourth unknown compound only tested positive for the first two. It is
soluble and contains a hydroxyl group. This alcohol is tertiary because it
tested negative on the third test. Because the substance is soluble, there
is not a very large hydrophilic portion, without there being other
hydrophobic portions. In other words, if it is a monofunctional
compound, it has four or five carbons. It could be tert-butanol, or a more
complex compound.
The fifth unknown compound tested positive for the first, fourth, and
sixth test. This means that the compound is a methyl ketone, and is
soluble in water, unlike the second unknown compound. This compound
could be methanone, which is soluble in water.
The hypothesis can be accepted, because after performing the
experiment, based on the physical and chemical properties, the
functional groups that were present could be distinguished.
Conclusion
As a result, from the experiments alone, certain functional groups that
are present within each compounded can be determined. However,
specific compounds cannot be known for sure, only a general idea of the

functional groups that are present or absent, and in some instances, the
relative size of the compound.

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