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In the identification of organic compounds, the following steps should be followed systematically
Haphazard methods will lead to wrong results, waste of chemicals and time.
As far as possible stick to the relative amounts reagents mentioned in the procedure. Use of excess of
chemicals will not always give the desired results.
When you are using volatile and inflammable solvents like ether and benzene, keep the test-tube away
from flame.
1. Physical Examination:
a) State- Solid/liquid
b) Colour- white/colourless / yellow /red/dark
c) Odour- Characteristic odour/odourless.
2. Ignition test:
Experiment
Two or three drops of the
given liquid or a small pinch
of the given solid is taken in a
spatula and heated, till the
substance catches fire and
burns
Observation
a) The compound burns
liberating lot of smoke
b) White fumes are
liberated
c) A voluminous porous,
black residue is left
behind
Inference
The compound is aromatic
and /or unsaturated
Compound may be urea
Compound may be
carbohydrate
Compound may be
unsaturated or a phenol or
amine or an amide or an
aldehyde
Compound is none of the
above
OR
Compound+1-2 drops of 1%
It is an easily oxidizable
compound like an unsaturated
compound or a phenol or an
amine or an aldehyde
Chlorine is present
Iodine is present
6. Solubility Test:
Bromine is present
Bromine is confirmed
a) Orange red globule
b) Violet globule
A green flame is
observed
Iodine is confirmed
The Purpose of this test is to find out the correct group to which the organic compound
belongs. For this purpose different solvents are tried and the solubility of the compound is
determined. This gives the group and the probable functional groups in that group. Then
classification reactions for that particular solubility group are carried out to find out the exact
functional group.
The solute and the solvent should be used in a proper proportion to judge solubility. For this
purpose 2-3 drops of the unknown liquid or about 0.2g of the unknown solid, about 5ml of the
solvent is added and shaken well.
The unknown liquid is said to be soluble in a solvent if,
a)
b)
c)
d)
Solubility Table
Soluble in
ether
Group
Compoun
ds
Insoluble in
ether (
Nitrogen
may be
present)
Soluble in Soluble In
5%
HCI 5% NaOH
(Nitrogen Is
Present)
Soluble in
cold conc
H2SO4
II
III
IV
Many low
mol wt.
compounds
and
Resorcinol
Amides and
carbohydrate
s e.g.
Urea
Glucose
Amines
e.g.
Aniline
O,m,p
Toluidines.
Monomethyl
Aniline
Dimethyl
aniline
Carboxylic
acids and
phenols
e.g.
Benzoic
alcohol,
Salicylic acid
Pehnol
O,m,pcresols
Alcohols
Aldehydes
Ketones
and esters
e.g.
Benzyl
alcohol,
Benzaldeh
yde
Acetophen
one
Methyl &
Ethyl
Benzoates
Insoluble
in cold
conc
H2SO4
(
Halogen
may be
present)
Nitrogen
is present
and
compound
is
insoluble
in water
and
5%HCI
VI
Aromatic
hydrocar
bonds
and their
halogen
derivativ
es
e.g.
Toluene
Biphenyl
Naphthal
ene,
Chlorobe
nzene,
Benzyl
Chloride
VII
Amides
and nitro
compound
s
Benzamid
em
Nitrobenzene mdinitroBenzene,
P-Nitro
toluene
4. Physical Constants:
If the given compound is a solid, determine the melting point. Note down the temperature when the
substance in the capillary tube has just melted
If the given compound is a liquid, determine the boiling point. See that the bulb of the thermometer is just
a little bit below the level of the side arm of the distillation flask. Note down the constant temperature
when about half of the liquid has distilled out. This is the observed boiling point. Since boiling point
decreases by one percent for every 1,000ft. Altitude above sea level, at Bangalore a correction of 3.5% is
to be added to the observed B.P. to get the correct B.P.
Correct B.P. = observed B.P. +3.5% correction.
Observation
A blue or a green coloured
solution or a ppt
Inference
Nitrogen is present
Sulphur is present
Violet coloured solution
OR
Sulphur is present
Black ppt
7. Classification reactions:
Depending on the solubility group to which the organic compound belongs, classification reactions of the
particular group are carried out to detect the functional group. For example, if the compound belongs to
IV group, tests for carboxylic acid and phenolic compounds are conducted.
Experiment
1) Compound dissolved in
water+ a few drops of
neutral ferric chloride
solution.
2) Compound + water +
bromine water dropwise.
Shake well
3) Phthalein Test:
Compound in a dry test
tube +1/2 its quantity of
phthalic anhydride + 2
drops of conc. H2SO4.
Heat till a dark red
coloured mixture is
formed. Pour the mixture
into a beaker containing
cold water.
Add excess of NaOH
solution and stir.
Observation
Inference
It is a phenolic compound
It is a phenolic compound
Reaction of amides:
Experiment
1) Compound +5ml of 4 N
NaOH solutions. Boil
and expose a wet red
limus paper to the
vapour. Expose a glass
rod dispped in HCi to the
gas
2) Biuret test:
The given compound is
heated in a dry test tube
till all ammonia is
expelled in the form of
white fumes. The solid
melts and then solidifies.
On cooling, to the white
residue a few drops of
NaOH solution and a
drop of copper sulphate
solution are added
Observation
Inference
It is an amide
1. Compound+Conc.
H2SO4 Heat
It is a carbohydrate
It is a Carbohydrate
It is a carbohydrate
It is a reducing sugar
Reactions of Carbohydrates:
3. Molisch Test
Solution of compound in
water+(alpha) Naphthol colution
in alcohol+conc. H2SO4 carefully
down the sides of the test tube
4. Compound+ Fehlings
solution ( Mix equal
volumes of Fehlings A
and Fehlings B
Solution)
Heat for a few minutes
Observation
Inference
It is a reducing sugar
6. Osazone Formation:
It is a reducing sugar
Compound dissolved in
water+phenyl hydrazine.
Heat the test tube in a beaker
containing boiling water.
Preparation of derivatives:
A. For amides(ex. Urea)- nitrate derivative
Dissolve a little urea in water taken in a test tube. Add Conc. HNO3 dropwise till a white
crystalline ppt appears. Filter the ppt, wash with minimum quantity of water and dry
Experiment
Observation
Inference
It may be ap or a s- amine but
not a t- amine.
OR
A solid is formed
A foul smell
5. Diazotisation and coupling
reaction:
a. Compound + di HCL.
Cool the test tube in ice
water for 2 minutes
b. Cool a solution of sodium
nitrite in water, in ice
water for 2 minutes.
It is a p-amine
OR
Yellow oily drops
It is a s-amine
OR
Green ppt
It is a t-amine
A red dye is formed
P-amine is confirmed
Derivatives:
(a) Acetyl or benzoyl derivatives of p-and s-amines:
To the compound taken in a dry test tube, add acetyl chloride or benzoyl chloride drop wise. A vigorous
reaction takes place in cold itself. Lot of heat is liberated and a solid if formed. Pour the reaction mixture
into water or dil NaOH solution. Filter the solid derivative and dry.
(b) Preparation of p-bromo derivative of t-amine:
To the compound taken in a test tube, add a solution ofbromine in glacial acetic acid and warm. Filter
the p-bromo derivative which separates out on cooling. Wash and dry.
Compound+water+a piece of
blue litmus paper. Shake well.
2. Compound +5% sodium
bicarbonate solution.
3. Esterification:
Compound +3-4 drops of
ethyl alcohol +2-3 drops of
conc. H2SO4. Heat and pour
the mixture into beaker
contining water. Add a little
NaOH soln to neutralize the
solution
4. Formation of acid amides:
Compound in a dry test tube+
A small quantity of
phosphorus pentachloride.
Heat slightly. Cool. Add
liquor ammonia to the mixture
carefully.
Reactions of Phenols:
Observation
Inference
It is an acidic compound
It is a carboxylic acid
It is a carboxylic acid
It is a carboxylic acid
It is a phenolic compound
It is a phenolic compound
It is a Phenolic compound
(Exception-p-cresol)
3. Phthalein Reaction:
Compound in a dry test tube+half its
quantity of phthalic anhydride + 2-3
drops of conc. H2SO4. Heat the test
tube till a homogeneous red coloured
mass is formed. Pour the mixture into
water taken in a beaker. Add NaOH
solution in excess
Derivative:
(a) Amide derivatives of carboxylic acids:
Take the given compound in a dry test tube and add phosphorus pentachloride. Heat and cool
the liquid product.
Add liquor ammonia dropwise carefully. A Vigorous reaction takes place with the liberation of
heat and white solid is formed.
(b) Preparation of acetyl derivative of salicylic acid(aspirin)
Take the given compound in a test tube. Add acetic anhydride (2ml) and glacial acetic acid
(2ml).
Heat and pour the mixture into dil NaOH solution taken in a beaker. Filter the white solid which
separates out, wash and dry.
(c) Preparation of benzoate derivative of phenol, m-cresol and p-cresol:
Add about one test tube of 5% NaOH to about 2ml of the phenol taken in a 100ml stoppered
conical flask. Add about 2ml of benzoyl chloride dropwise with vigorous shaking. Destroy any
excess of benzoyl chloride by the addition of excess of NaOH solution. Cool, filter the
precipitate,
wash and dry.
Observation
Inference
It is an alcohol
It is an alcohol
It is an aldehyde or a ketone
It is an aldehyde or a ketone
It is an aldehyde or a Ketone
It is an aldehyde
It is an aldehyde
It is a ketone
It is a ketone
It is a methyl ketone
2. Compound + 20%
sodium jhydroxide
A white precipitate is formed
solution. Boil for about
10 minutes. Cool and add
excess of dil H2SO4.
3. Compound + 2-3drops of
ethyl alcohol. Shake.
Add about 0.2g
hydroxylamine
hydrochloride + about
5ml of 2N NaOH
solution. Boil gently;
cool Add 1-2 drops for
neutral ferric chloride
solution and excess of dil
HCI
It may be an ester
It is an ester
It is an ester
It is an ester
Preparation of derivatives:
(A) Benzoic acid from benzyl alcohol.
Take a mixture of a few drops of benzyl alcohol and about 5ml of 10% sodium carbonate
Solution in a 100ml concial flask provided with a one holed cork carrying a long glass tube which
serves as a condenser. Heat the solution and add about 15ml of saturated solution of potassium
permanganate slowly till a light pink colour remains. Boil for a few more minutes. Filter off
brown ppt of managanese dioxide. Add dil H2SO4 to the filtrate till the solution is acidic. On
cooling benzoic acid separates out as a white solid. Filter, wash and dry.
(B) Preparation of phenyl hydrazone derivative of benzaldehyde and acetophenone:
To about 5ml of phenyl hydrazine taken in a test tube add a few drops of glacial acetic acid and a
few drops of benzaldehyde or acetophone. Shake well. Filter off the yellow ppt. of the phenyl
hydrazone. Wash and dry.
(c) Preparation of benzoic acid from methyl and ethyl benzoates:
To about 2ml of methyl or ethyl benzoate taken in 100 ml concial flask provided with a one holed
cork carrying a long glass tube, add about 25 ml of 20% NaOH solution. Boil for about 10-15
minutes. Acidify with HCI and cool. Filter off the precipitate of benzoic acid, wash and dry.
Experiment
Observation
Inference
It is an aromatic compound
2. Small quantity of
substances as above+5
ml of dimethyl sulphate.
Heat the solution
strongly with shaking
It is an aromatic compound
It is an aromatic compound
The following reaction is carried out only if the presence of chlorine in the given compound has been
established by elementary analysis.
Compound + silver nitrate
solution+5ml of ethyl alcohol.
Shake well.
White ppt
No ppt
Preparation of Derivatives:
A. Benzzoic acid from toluene:
For procedure, see the method of preparation of benzoic acid from benzyl alcohol in V group.
Use toluene instead of benzyl alcohol.
B. Pictrate derivative of naphthalene:
To a strong solution of naphthalene in about 3 ml of benzene add a stron solution of picric acid in
about 3ml of benzene. Mix the two solutions. Evaporate the solution to dryness near the window
to get the solid.
C. Preparation of nitro derivatives for biphenyl, chlorobenzene and benzyl chloride.
Take the compound in a test tube and add a mixture of 3ml. of fuming nitric acid and 3ml of
conc. Sulphuric acid, Boil with shaking for about 5 minutes. Add one or two drops of the mixture
to a little ice water taken in another test tube.
If a yellow solid separates out, nitration is complete. If a yellow emulsion is formed nitration is
incomplete and the mixture must be heated for a few more minutes. Finally, pour the mixture into
ice water. Filter off the yellow solid, wash and dry.
CLASSIFICATION REACTIONS FOR VII GROUP OF THE SOLUBILITY TABLE
Compounds belonging to this group contain nitrogen. They are insoluble in water and 5% HCI.
Such compounds are,
Amides- Benzamide
Nitro compounds- Nitrobenzene , mdinitrobenxene, p-nitrotoluene
Experiment
Test for amides
Compound + excess of 2N NaOH
solution. Boil well and expose a
wet red litmus paper to the vapours;
also expose the vapours to glass rod
dipped in HCI. Cool the solution
and add excess of HCI
Observation
Inference
It is an amide
It is a nitro compound
3. Janowskys reaction:
Compound+acetone+NaOH Pale yellow coloured
solution
solution. Shake well
Preparation of derivatives:
It is a mononitro compound
It is a dinitro compound
To a little benzamide taken in a test tube, add about 5ml of 50 % H2SO4. Boil well and pour the
mixture into ice water taken in a beaker. Filter off the precipitated benzoic acid, wash and dry.
B. Preparation of M-dinitrobenzene from nitrobenzene:
To about 3ml of nitrobenzene, add about 3 ml of fuming HNO3 and 3ml of conc- H2SO4. Boil
for about 5 minutes with shaking. Pour the mixture into ice water. Filter off the yellow solid,
wash and dry.
C. Preparation of derivative from m-dinitrobezene
Prepare a strong of m-dinitrobenzene in 3ml of benzene. To this add a strong solution of
naphthalene in 3ml of benzene and mix well. Concentrate and cool the solution or evaporate the
solution to dryness near the window to get the derivative.
D. Preparation of p-nitrobenzoic acid from p-nitro toluene:
For procedure, see method of preparation of benzoic acid from benzyl alcohol in V group. Use pnitro toluene instead of benzyl alcohol.