SEPERATION OF TERNARY ORGANIC MIXTURE USING MICROSCALE TECHNIQUE
Aim: To separate given ternary mixture.
Theory:
A mixture of organic compounds may be in the solid or liquid form or may consist of a solid dissolved
or suspended in a liquid. If a solid and a liquid are present it is usually unwise to expect separation to
be accomplished by filtration because the liquid phase almost certainly contains some dissolved solid
and traces of the liquid component may be difficult to remove from the solid compound. The
methods of isolating pure samples of the components from a mixture may be either physical or
chemical. The physical method consists of fractional distillation and is applicable only if there is a
wide difference between the boiling points of the two compounds and provided that an azeo-trope
is not formed. The chemical method of separating two compounds depends on their differing
solubility in water, ether, dilute acid or alkali.
CHEMICAL SEPERATION OF ORGANIC COMPOUND (TERNARY MIXTURE)
1. Nature of the mixture: The given mixture contains solid-solid-liquid state.
2. Solubility Test of the mixture: The given ternary mixture consists of 2
water insoluble and 1 water immiscible compounds.
3. Determination of type :
Tests Observation Inference
Test for acid:
Compound+ sat. NaHCO3. Strong Acid present
Shake well and filter. Effervescence
Filtrate+ conc. HCl
Test for phenol: Soluble + reprecipitated
Residue washed with water by adding conc. HCl Phenol Present
and treated with 10% NaOH.
Test for base: Soluble + reprecipitated by
Residue washed with water adding 10% NaOH to filtrate Base Present
and treated with dil. HCl.
(Increased Quantity)
Conclusion: Since Only three components are present i.e., water insoluble acid, water
immiscible base and water insoluble phenol.
Bulk Separation of ternary mixture
Test Separation Agent Observation
Water Insoluble Acid NaHCO3 Effervence of CO2 + reprecipitation by conc. HCl.
Water Immiscible Base Conc. HCl Soluble in conc. HCl + reprecipitated ny adding 10%
NaOH
Water Insoluble Phenol NaOH Soluble + reprecipitated by adding HCl
FOR COMPOUND 1(Water insoluble acid): -
I. PRELIMINARY TEST:
Test Observation Inference
Physical State Solid Acids, Phenols, Amides,
Hydrocarbons, Aniline, etc. May
be present
Color White Benzoic acid, Salicylic acid,
Naphthalene, etc. May be
present.
Odor Indistinct Benzoic acid, Salicylic acid, etc.
May be present.
Water solubility test soluble Acid, phenol, hydrocarbon may be
present
Flame test: Sooty flame Aromatic compounds may be present
Take small amount of
compound on a porcelain
piece and heat in an
oxidizing flame
Beilstein Test: compound on No green flame Halogen absent
Cu foil and heat in an observed
oxidizing flame
Test for unsaturation: Unsaturated compound or easily
KMnO4 test: 0.01g of oxidizable compounds are present.
compound + 2cm of diluted Decolorization of
KMnO4, solution KMnO4
CONCLUSION: Aromatic unsaturated compound may be present
II. DETECTION OF ELEMENTS (N, S & Halogen):
Preparation of Lassaigne Filtrate (Sodium Fusion Test):
1. Heat a small fresh cut, piece of sodium metal in a dry fusion tube till it melts.
2. Add a small amount of the dry substance (2-3 drops, if liquid) to the molten sodium.
3. After the initial reaction has subsided, heat the fusion tube further to red hot and then drop it in
about 5 cm3 of distilled water taken in porcelain dish covering it immediately with an asbestos
sheet.
4. Carry out two or more fusion tubes in the similar way and concentrate the content of the dish to
half of it’s volume.
5. Cool and filter the solution.
Test Observation Inference
Test for nitrogen: No coloration Nitrogen
2 drops of filtrate + freshly absent
prepared FeSO4, boil + 2-3
drops of H2SO4
Test for Sulphur: No coloration Sulphur absent
2 drops of filtrate + 1 drop of sodium nitroprusside
solution
Test for halogen: No precipitate Halogen
0.5cm3 of filtrate +0.5cm3 absent
of dilute HNO3
CONCLUSION: -
Hence the elements Nitrogen, Sulphur and halogen are absent. Therefore, the
compound 1 contains C, H, [O] only. Therefore, functional groups such as acids,
phenol, ketones, aldehydes etc. can be present.
DETERMINATION OF THE FUNCTIONAL GROUP OF COMPOUNDS
Test Observation Inference
Test for carboxylic acid Soluble with brisk Carboxylic acid
Compound+ sat. NaHCO3 effervescence present.
solution
CONCLUSION: In the given compound carboxylic acid is present.
Separation of acids: -
C.T. for Benzoic acid:
Test Observation Inference
Compound + Water + No buff ppt soluble in Benzoic Acid absent
Neutral FeCl3 solution NH4OH
C.T. for Cinnamic acid:
Test Observation Inference
Compound + Ethyl alcohol No White ppt insoluble in Cinnamic acid absent.
+ CaCl2 solution acetic acid
C.T. for Salicylic acid:
Test Observation Inference
0.5 gm of compound + 5
drops of CH3OH + 3 drops Pleasant smell of methyl
of conc. H2SO4 and heat salicylate (Oil of winter Salicylic acid Confirmed.
gently on water bath. Cool green)
and pour this into about 4ml
of water. Add solid Na2CO3
Conclusion: The first compound is Salicylic Acid.
FOR COMPOUND 2 (Water insoluble phenol): -
I. PRELIMINARY TEST:
Test Observation Inference
Physical State Solid Acids, Phenols, Amides,
Hydrocarbons, Aniline, etc. May
be present
Color Pink Brown β-Naphthol may be present
Odor Carbolic β-Naphthol, α-Naphthol may be
present
Water solubility test soluble Acid, phenol, hydrocarbon may be
present
Flame test: Sooty flame Aromatic compounds may be present
Take small amount of
compound on a porcelain
piece and heat in an
oxidizing flame
Beilstein Test: compound on No green flame Halogen absent
Cu foil and heat in an observed
oxidizing flame
Test for unsaturation: Decolorization Unsaturated compound or easily
oxidizable compounds are present.
KMnO4 test: 0.01g of of KMnO4
compound + 2cm of diluted
KMnO4, solution
CONCLUSION: Aromatic unsaturated compound may be present
II. DETECTION OF ELEMENTS (N, S & Halogen):
Preparation of Lassaigne Filtrate (Sodium Fusion Test):
1. Heat a small fresh cut, piece of sodium metal in a dry fusion tube till it melts.
2. Add a small amount of the dry substance (2-3 drops, if liquid) to the molten sodium.
3. After the initial reaction has subsided, heat the fusion tube further to red hot and then drop
it in about 5 cm3 of distilled water taken in porcelain dish covering it immediately with an
asbestos sheet.
4. Carry out two or more fusion tubes in the similar way and concentrate the content of the
dish to half of its volume.
5. Cool and filter the solution.
Test Observatio Inference
n
Test for nitrogen: No
2 drops of filtrate + freshly coloration Nitrogen
prepared FeSO4, boil + 2-3 absent
drops of H2SO4
Test for Sulphur: No Sulphur absent
2 drops of filtrate + 1 drop of sodium nitroprusside coloration
solution
Test for halogen: No Halogen
0.5cm3 of filtrate +0.5cm3 of precipitate absent
dilute HNO3
CONCLUSION: -
Hence the elements Nitrogen, Sulphur and halogen are absent. Therefore, the
compound 1 contains C, H, [O] only. Therefore, functional groups such as acids,
phenol, ketones, aldehydes etc. can be present.
Phenols containing C, H, (O) as the Elements: -
Test Observation Inference
Compound + 10 drops of Phenolic -OH group is
ethyl alcohol + 2-3 drops Blue Color present.
neutral FeCl3 solution
Separation of Phenols:
C.T. for α-Naphthol
Test Observation Inference
Compound + NaOH solution No color α-Naphthol absent.
+ 1 drop of CCl4 . Add
copper foils and warm.
C.T. for β-Naphthol
Test Observation Inference
Compound + NaOH +
solution, heat to dissolve. Blue Color β-Naphthol is Confirmed.
Add CHCl3 and warm.
Conclusion: The second compound is β-Naphthol.
FOR COMPOUD 3 (water immiscible base): -
I. PRELIMINARY TEST:
Test Observation Inference
Physical State Solid Acids, Phenols, Amides,
Hydrocarbons, Aniline, etc. May
be present
Color Yellowish Brown Aniline, Nitroaniline, etc, may
be present
Odor Fishy Aniline, p-Toluidine, etc. may be
present.
Water solubility test soluble Acid, phenol, hydrocarbon may be
present
Flame test: Sooty flame Aromatic compounds may be present
Take small amount of
compound on a porcelain
piece and heat in an
oxidizing flame
Beilstein Test: compound on No green flame Halogen absent
Cu foil and heat in an observed
oxidizing flame
Test for unsaturation: Decolorization
KMnO4 test: 0.01g of of KMnO4
compound + 2cm of diluted Unsaturated compound or easily
oxidizable compounds are present.
KMnO4, solution
CONCLUSION: Aromatic unsaturated compound may be present
DETECTION OF ELEMENTS (N, S & Halogen):
Preparation of Lassaigne Filtrate (Sodium Fusion Test):
1. Heat a small fresh cut, piece of sodium metal in a dry fusion tube till it melts.
2. Add a small amount of the dry substance (2-3 drops, if liquid) to the molten sodium.
3. After the initial reaction has subsided, heat the fusion tube further to red hot and then drop
it in about 5 cm3 of distilled water taken in porcelain dish covering it immediately with an
asbestos sheet.
4. Carry out two or more fusion tubes in the similar way and concentrate the content of the
dish to half of its volume.
5. Cool and filter the solution.
Test Observation Inference
Test for nitrogen: coloration Nitrogen
2 drops of filtrate + freshly present
prepared FeSO4, boil + 2-3
drops of H2SO4
Test for Sulphur: No coloration Sulphur absent
2 drops of filtrate + 1 drop of sodium nitroprusside
solution
Test for halogen: No precipitate Halogen
0.5cm3 of filtrate +0.5cm3 absent
of dilute HNO3
Hence the element Nitrogen is present. Therefore, the compound 3 contains C, H, [O] &
N. Therefore, functional groups such as amine, aniline, etc. can be present.
Test Observation Inference
1) Compound + conc. HCl + Primary amine (-NH2 grp)
solution of NaNO2 + β- Red – Orange ppt Present.
Naphthol solution.
2) Mullikan Baker test Black color -NH2 grp present
Amines containing C, H, (O), & N as the elements:
Test Observation Inference
Diazotization Red – Orange ppt Aniline confirmed
Mullikan Baker test Black color Aniline confirmed
C.T. for Aniline:
Conclusion: The third compound is Aniline.
Result: -
Element Nature Function M.P/B. P Structure and name
present al group
C, H, [O] Water -C, H, [O]
insoluble (carboxylic
acid acid)
C, H, [O] Water -C, H, [O]
insoluble (Phenol)
phenol
C, H, [O] & Water C, H, [O] &
N immiscible N (amine)
base
