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Qualitative analysis of organic mixture (Binary and Ternary) chart for M.Sc.
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Experiment Findings · March 2019

DOI: 10.13140/RG.2.2.28446.18247

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 Nagar Shikshan Vikas Mandal’s
SHRI MADHAVRAO PATIL MAHAVIDYALAYA,
MURUM, TQ. OMERGA, DIST. OSMANABAD
ORGANIC QUALITATIVE ANALYSIS

The Systematic analysis of a two component/three component mixture involves the following points.
1) Nature of the mixture
2) Type of the mixture
3) Separation of the mixture into two/three component.
4) Systematic analysis of each component which involves following
a) Preliminary Tests.
b) Detection of elements.
c) Detection of the functional group.
d) Physical constants. (M.P. OR B.P.)
e) Conformation with preparation of derivatives.
f) Result.

Separation of Two Components from given Binary Mixture of Organic Compounds Qualitatively and
Identification of its components

1. Nature of binary mixture:-

The nature of the binary mixture may be of three types:-
i) Solid – Solid
ii) Solid – Liquid
iii) Liquid – Liquid

 Each of these can be either homogeneous or heterogeneous.

The solid-solid mixture and liquid – liquid mixture is identified directly by observation of the physical
state of the mixture.
 In order to identify the solid – liquid mixture, a small quantity of mixture is placed on a watch glass and
is evaporated. If the liquid part gets evaporated and solid residue is left behind then the given mixture
belongs to solid – liquid type.
If no solid residue is left behind, it is liquid – liquid type.

2. Determination of the Type

I) Type determination of Water insoluble mixture

Sr. Test Observation Inference

No.
1. Mixture + 10% NaHCO3  One component is soluble with Acid Present.
Solution (Shake well & effervescences of CO2 and
Filter) reprecipitated by adding conc. HCl
to the filtrate.
 Insoluble Acid Absent
2. Mixture or Residue + 10%  One component is soluble and Phenol Present.
NaOH Solution (Shake well reprecipitated by adding Conc.
& Filter)
1
 HCl to filtrate. Phenol Absent
 Insoluble
3. Mixture or Residue + dil.  One component is soluble and Base Present.
HCl Solution (Shake well & reprecipitated by adding 10%
Filter) NaOH Solution to filtrate.
 Insoluble Base Absent
4. Mixture or Residue + 10% Insoluble Neutral Present
NaHCO3 or 10% NaOH or
dil. HCl Solution

II) Type determination for water miscible (solution) substance.

Test Observation Inference

Litmus test a)Blue litmus turns red Acid or Phenol present
A) Add few drops on litmus paper b) Red litmus turns blue Base present
c) No change on either litmus Neutral present
Distinguish between acid and Effervescence of CO2 Acid is present
phenol
Substance + 4 drops of 10 %
NaHCO3 NO Effervescence of CO2 Phenol is present

Conclusion: - Type of the given Binary mixture is -------------- + ------------

3) Separation of the mixture into two components.

a) Separation of solid – solid Binary mixture.

 Acid + Phenol
Take the given mixture in a beaker and add about 50 ml of 10% NaHCO3 solution. Stir it with glass rod
till the effervescence ceases. Filter the contents. Residue is Phenol, wash it with water and dry. Filtrate
contains Acid. Add conc. HCl to the filtrate. Acid component reappears. Filter, wash it with water and
dry.
Reactions:- R-COOH + NaHCO3 —› R-COONa + H2O + CO2↑
R-COONa + HCl —› R-COOH + NaCl
 Acid + Amine
Take the given mixture in a beaker and add about 50 ml of 10% NaHCO3 solution. Stir it with glass rod
till the effervescence ceases. Filter the contents. Residue is Amine, wash it with water and dry. Filtrate
contains Acid. Add conc. HCl to the filtrate. Acid component reappears. Filter, wash it with water and
dry.
Reactions:- R-COOH + NaHCO3 —› R-COONa + H2O + CO2↑
R-COONa + HCl —› R-COOH + NaCl
 Acid + Neutral
Take the given mixture in a beaker and add about 50 ml of 10% NaHCO3 solution. Stir it with glass rod
till the effervescence ceases. Filter the contents. Residue is Neutral, wash it with water and dry. Filtrate

2
 contains Acid. Add conc. HCl to the filtrate. Acid component reappears. Filter, wash it with water and
dry.
Reactions:- R-COOH + NaHCO3 —› R-COONa + H2O + CO2↑
R-COONa + HCl —› R-COOH + NaCl
 Phenol + Amine
Take the given mixture in a beaker and add about 50 ml of 10% NaOH solution. Stir it with glass rod.
Filter the contents. Residue is Amine, wash it with water and dry. Filtrate contains Phenol. Add conc.
HCl to the filtrate. Phenol component reappears. Filter, wash it with water and dry.
Reactions:- Ar-OH + NaOH —› Ar-ONa + H2O
Ar-ONa + HCl —› Ar-OH + NaCl
 Phenol + Neutral
Take the given mixture in a beaker and add about 50 ml of 10% NaOH solution. Stir it with glass rod.
Filter the contents. Residue is Neutral, wash it with water and dry. Filtrate contains Phenol. Add conc.
HCl to the filtrate. Phenol component reappears. Filter, wash it with water and dry.
Reactions:- Ar-OH + NaOH —› Ar-ONa + H2O
Ar-ONa + HCl —› Ar-OH + NaCl
 Amine + Neutral
Take the given mixture in a beaker and add about 50 ml of dil. HCl solution. Stir it with glass rod. Filter
the contents. Residue is Neutral component, wash it with water and dry. Filtrate contains Amine. Add
10% NaOH solution till amine component reappears. Filter, wash it with water and dry.
Reactions:- R-NH2 + HCl —› R-NH2.HCl
R-NH2.HCl + NaOH —› R-NH2 + NaCl + H2O

b) Separation of Solid- Liquid mixture:-

Take all the given mixture in a dry distillation flask and place one porcelain piece in it. Attach the flask
to the water condenser. Then attach a thermometer to the flask in such a way that the bulb of the thermometer is
near to the outlet of the flask.
Heat the flask on a boiling water bath. Start collecting the volatile (Boiling point below liquid in a dry
test tube. Note down the Constant boiling point. After collecting one test tube component, stop heating and
pour the remaining liquid on a dry watch glass or evaporating dish and with mouth; solid component will be
obtained. Dry it on filter paper and find out its melting point.

c) Separation of liquid-liquid mixture

Take all the given mixture in a distillation flask, place

one porcelain piece and attach the flask to the water
condenser. To attach a thermometer to the flask and heat
over a boiling water bath. The volatile component will
come first. Collect one test tube volatile component. Note
down constant boiling point. Then stop heating remove the
water bath and dry the flask from outside and heat he flask
on the wire gauge. This time some volatile component may
come out. Discard the middle fraction up to 100 0c. After
1000C start collecting the second pure non-volatile
component in another dry test tube. Note down the highest
temperature i.e. the boiling point of the second liquid

3
PURIFICATION OF THE COMPONENTS BY RECRYSTALLISATION/SUBLIMATION

 After the separation of compounds, it should purify before the Individual Analysis. Generally organic
compounds are purified through recrystlisation and Sublimation method.

A. Recrystallisation: The separated components organic compounds may contain some soluble and
insoluble impurities, which are removed by crystallization method. The insoluble impurities after
crystallization remain on filter paper while soluble impurities are left behind in the mother liquid.
Selection of a solvent for crystallization:

1. The solvent should be such that the given compounds must be insoluble in that solvent at room
temperature and completely soluble in it under hot condition.
2. The choice of the solvent is made in the following order.
1) Water 2) Alcohol + Water mixture 3) Alcohol

 From hot Water :

Take about 0.5 g of the substance in a clean test tube. Add 5 ml distilled water and heat it using test tube
holder. Shake the test tube during heating, till most of the compound dissolves. In this way prepare a saturated
solution of the substance in water (Add more water if compound does not dissolve) remain on filter paper which
should be discarded. The filtrate on natural cooling deposit fine crystals, [After cooling if crystals are not
obtained, concentrate the filtrate by heating on wire gauge and then cool it again]
Now, filter these crystals on a hursh funnel, wash with distilled water to remove adhered mother liquor
or remove the solvent from the test tube by using rubber teat pipette hold the test tube under hot air flow (using
hair dryer) and collect dry crystals on paper find its melting point.

(II) From Alcohol :

 If the given substance is insoluble in hot water. Then water cannot be used for recrystallization.
Then ethyl alcohol is tried. Take about 0.5 g of the substance in a clean and dry test tube. Add about 5 ml
ethyl alcohol and place one porcelain piece in it. Then hold the tube in hot water bath with constant shaking till
most of the substance dissolves. Filter the hot solution through dry fluted filter paper into another test tube.
The insoluble impurities remain on filter paper, which should be discarded the filtrate on natural cooling fine
crystals. [If crystals are not obtained on cooling add little distilled water] Filter these crystals funnel or remove
the solvent from the test tube by using rubber teat pipette. Hold the test tube air flow (Use hair dryer) and
collect dry crystals on paper find its melting point.

(III)From Water-Alcohol :
If the given substance is insoluble in hot water but soluble in cold alcohol then pure water or
pure Alcohol cannot be used for recrystallization in such cases combination of water alcohol in very
high proportions is used.

The solvents used for the recrystallisation of components of various groups are summarized below.
Components Solvents
 Acid Hot water
 Phenol Hot water or Aqueous alcohol
 Amines Aqueous alcohol, Alcohol

4
  Neutral Water, Alcohol, Acetic acid

B. Sublimation :
Sublimation is a process in which the substance on heating directly passes into vapors state without first
passing into the liquid state. The vapors get collected on the cooler part and give pure crystals.

Note :- This method is used under following conditions.

i) If the given organic compound is insoluble in-hot water, hot alcohol, hot alcohol +water as
solvent.
ii) It is used only for solid compound.

Procedure :-
1. Take the given substance in a dry evaporating dish, kept on a sand bath, supported on a
tripod stand.
2. The dish is covered with a filter paper which has been perforated with a number of small
holes.
3. An inverted funnel is placed over the filter paper is shown in fig.
4. The nozzle of the funnel is closed with cotton plug.
5. The dish is gently heated so that the vapors, which passes through the holes deposit as pure
crystals on the inner side of the funnel.
6. The crystals are also collected on the filter paper.
7. Find out the melting point of crystalline substance.

Separation of Three Components from given Ternary Mixture of Organic Compounds Qualitatively and
Identification of its components
 For the ternary mixture separation we have use physical method that depending on solubility of
compounds in organic solvent (Ether or DCM).
 Ternary mixture also separated by using chemical method that can be describe above, but nature
of all constituents in the mixture must different.
 If nature of two or three compounds are same then we can’t separate by chemical method.

 Choice of Extraction Solvent

Although water is almost always one of the liquids in the liquid-liquid extraction process, the choice
of organic solvent is quite wide. A good extraction solvent needs five essential features:
1) has high solubility for the organic compound.
2) be immiscible with the other solvent (usually water).
3) has a relatively low boiling point so as to be easily removed from the compound after extraction.
4) extract little or none of the impurities and other compounds present in the mixture.
5) be nontoxic, nonreactive, readily available, and inexpensive.
Table 1 below shows some organic solvents used in extraction.

Table 1: Some common extraction solvents.

5
 Thus DCM is the good solvent for ternary mixture separation, it has some advantages over other solvent
like Diethyl ether these are :
1. It is inflammable, so safe for use in lab.
2. Very slight soluble in water, so avoid mixing in Aqu. layer
3. Somewhat cheaper than Diethyl ether.
Note: Density of DCM is higher than water, so organic layer is set down in separating funnel which is
opposite in case of ether solvent.

Flow chart for separation of Ternary mixture by using DCM solvent

6
7
8
  Individual Analysis
Identification of Organic Compounds
 Preliminary Tests-
Test Observation Inference
i. Physical State Solid Acids, Phenols, Amines, Anilides,
Hydrocarbons may be Preesent.
ii. A. Colour (Solids) White Benzoic acid, Salicylic acid, Naphthalene,
Acetanilide may be Present.
Cream Cinnamic acid may be Present.
Light pink α-Naphthol may be Present.
Pink Brown β-Naphthol may be Present.
White buff / Pinkish p-Toluidine, Resorcinol may be Present.
Light buff Diphenylamine may be Present.
Yellow p-Nitroaniline/Nitro Compounds may be
Present.
Light Yellow m-Dinitrobenzene may be Present.
Orange O-Nitro aniline May be Present.
Red Azo compounds, β- Napthoquinone,
Alizarine may be present.
B. Colour (Liquids) Colourless Acetone, Acetophenone, Methyl Ethyl
(reddish-brown colour Ketone, Methyl Acetate, Ethyl Acetate,
appears due to oxidation) Chloroform, Chlorobenzene May be Present
Yellow Aniline, Dimethylaniline, Nitro Benzene May
be Present.
iii. Odour Indistinct Benzoic acid, Salicylic acid, p-Nitroaniline,
Acetanilide m-Dinitrobenzene may be
Present.
Carbolic α-Naphthol, β-Naphthol may be Present.
Fishy p-Toluidine, Aniline, Dimethyl Aniline may
be Present.
Pleasant (Alcoholic) Alcohols, Ketones, Chloroform May be
Present.
Sweet Aliphatic And aromatic Halogenated
Compounds May be Present.
Pungent irritating Acetic acid, acetic anhydride, Lower
acids, lower aldehydes, acid halides,
thioacids may be present
Mouse-like Acetamide, acetonitrile
Cinnamon like Cinnamic acid may present
Bitter Almond Aromatic aldehyde like Benzaldehyde,
Nitrobenzene, Nitrotoluenes May be Presents.
Pleasant-fruity Ester may be present
Pleasant, sweet Chloroform, diphenylamine, alcohols
Garlic Thiophenols, Thioalcohols May be presents.
Benzene Like Odour Benzene, Toluene, Xylenes May be Presents.
Fragrant Diphenylamine may be Present.
Camphor-like Pinacol, hexachloroethane
Pyridine-like Heterocyclic bases
9
 Naptha ball Like Naphthalene may be Present.
Odourless Carbohydrates, aromatic acid, glycerol, solid
aliphatic acid May be Present.
iv. Solubility in Water Insoluble Acids, Phenols, Amines, Anilides,
Hydrocarbons may be Preesent.
v. Saturation Test- Action of Decolourisation Unsaturated compound or easily oxidisable
KMnO4 (Baeyer Test) compounds, Exception Hydroxy acids, may
Compound + KmnO4(dil.) be present
No Decolourisation Saturated compound is Present.
vi. Litmus Test – a) Acidic Carboxylic acids, Nitrophenols, Sulphonic
A small amount of the sub is acids, Acid chlorides, Acid anhydries May be
shaken with water and a drop of the presents.
solution is tested for litmus action b) Faintly Acidic Phenols, Cresols may be presents.
c) Faintly Basic Amines May present.
d) Neutral Alcohols, Aldehydes, Ketones, Hydrocarbons
Carbohydrates May be Presents.
vii. Flame Test
Heat the compound on copper wire Sooty Flame Aromatic compound is Present.
Non sooty Flame Aliphatic compound is Present.

 Detection of Elements-
Preparation of Sodium Fusion Extract-
Lassaignes Test:- Heat a small freshly cut piece of sodium metal in a dry fusion tube till sodium melts.
Cool and add given compound to the molten sodium, heat the fusion tube to red hot and then drop it in
about 15 ml of distilled water taken in china dish. Carry out three more fusions in the similar way.
Concentrate the solution of the dish to half its volume by boiling. Cool and filter the solution. The
filtrate, known as sodium fusion extrat is used for the detection of Elements.
This test is aimed to identify the nitrogen, sulphur and halogen in organic compounds and it can
be carried out by fusion of the organic substance with sodium metal in the presence of excess soda lime
(NaOH/CaO). The following equations express the reaction of element after reacted with sodium:-

Na + C + N →NaCN (nitrogen compounds)

2 Na + S → Na2S (sulfur compounds)

Na + X → NaX (halogen compounds, X = Cl, Br, ..)

Test Observation Inference

1. Test for Nitrogen
A) Sodium Extract (2 ml) + Freshly Prepared Green or Blue Precipitate Nitrogen is Present.
Ferrous Sulphate solution Boil and Cool. Add or Colour
dil. H2SO4.
B) Sodium Extract (2 ml) + FeCl3
Blood red colour S And N Present.
2. Test for sulphur
Sodium Extract (2 ml) + Sodium Purple or Violet colour Sulphur is Present
Nitroprusside.
3. Test for Halogens
Sodium Extract (2 ml) + Conc. HNO3, Boil Precipitate Halogens are Present
10
and Cool. Add AgNO3.
If Halogen present proceed as follows
Sodium Extract (2 ml)+ Conc. HNO3 + A) Violet Colour Iodine Present.
Chlorine Water + 1 ml Chloroform + Shake
well & Observe the Colour of Chloroform B) Yellow Colour Bromine Present.

C) Colour less Chlorine Present.

Conclusion: - The compounds contains C, H, (O) and ---- as the Elements.

 Detection of Functional Group(s)-

Test Observation Inference

1. Comp. + 10% NaHCO3 Soln Effervescence of CO2 PPT By -COOH group is Present.
Adding Conc. HCl
2. Comp. + Water + Neutral FeCl3 Blue, Violet or Green Colour. –OH group is Present.
Solution.
3. Comp.+ NaOH Soluble and PPt by adding Phenolic –OH group is Present.
Conc. HCl
4Comp. (if liquid) + Na metal Soluble with effervescence Alcoholic –OH present
5. Comp.+ Dil HCl Soluble And PPT by adding Amino –NH2 group is present.
NaOH
6.a) Comp. + Alcoho l+ 2,4 Yellow, Orange or Red PPT Aldehydes or Ketones Present.
dinitrophenylhydrazine (Boil) Violet colour develops Aliphatic aldehyde present
b)Comp. + Schiff’s Reagent Pink colour slosly develops Aromatic aldehyde present

7. Comp. + NaOH + Sodium Red colouration Ketone present

nitroprusside(freshly prepare)
8. a) Comp.+NaOH + Zn Dust (Boil) Black or Gray PPT
NO2 group is present.
b) Comp. + Conc. HCl+ Zn dust + NaNO2 Orange dye stuff
freshly prepare β- Napthol in NaOH
9. Comp.+ NaOH (Boil) Ammonia gas evolves turns Amide –CONH2 group Present.
moist turmeric paper brown
10. Comp.+Conc. HCl (Boil) Cool and add Red dyestuff Anilide –NHCO group present
Cold NaNO2+β–Naphthol in NaOH.
11. Comp.+1 ml H2O+2,3 drops 10% ἀ– Reddish Violet Colouration at Carbohydrates present.
Naphthol in alcohol+1 ml Conc. H2So4 the Junction of two layer
12. If all above test fails HydroCarbons Present.

Conclusion: - The compound contains ----------------- as the Functional Group(s).

 Confirmatory Tests of respective Functional group

 Compounds containing C, H and (O) as the Elements-
C.T. for Acid
Test Observation Inference
10 mg substance + sat. NaHCO3 Effervesces of CO2 Acid is Confirmed.
11
Separation Of Acid a)Buff or Brown PPt Soluble in Dil. 1)Benzoic Acid (Mp. 122oC)
Neutral Solution of Acid Substance + HCl 2) Cinnamic acid (Mp. 133oC)
2 drops of FeCl3 3) Phthalic Acid (Mp. 133oC)

1) Salicylic Acid (Mp. 158oC)

b) Violet colour discharged by dil 2) Aspirin (Mp. 135oC)
HCl
Acetic acid (Bp 118oC )

c) Red colour disappear in dil HCl

Neutral Solution : 0.1 gm of given acid substance + 1 ml NH4OH boil well till ammonia gets evolved
(i.e. moist turmeric paper should not turn brown). Use this solution for separation of above acids.

Separation of acids
C.T. for Benzoic Acid –

Test Observation Inference

1. Comp. + Ethyl alcohol + 2-3 drops of Pleasant smell of Ethyl Benzoic Acid is Confirmed.
conc. H2SO4 and Heat. benzoate
2. Comp. + Water + Neutral FeCl3 Solution. Buff ppt soluble in NH4OH. Benzoic Acid is Confirmed.

C.T for Cinnamic Acid-

Test Observation Inference
1. Comp. + Ethyl alcohol + CaCl2 White ppt insoluble in acetic Cinnamic Acid is Confirmed.
Solution. acid.
2. Comp. + 2 drops of 1% KMnO4 solution Decolourisation of KMnO4 Cinnamic Acid is Confirmed.
+ 1 ml of Na2CO3 Solution. solution.

C.T for Salicylic Acid-

Test Observation Inference
1. 0.5 gm of Compound + 5 drops of Pleasant smell of methyl Salicylic acid is Confirmed.
CH3OH + 3 drops of conc. H2SO4 and Heat salicylate (Oil of Winter
gently on Water bath. Cool and pour this Green).
into about 5 ml of water. Add solid
Na2CO3.

C.T. for Oxalic Acid:-

Test Observation Inference

1.Neutral Solution of Acid Substance + White PPT insoluble in dil. Acetic Oxalic Acid is Confirmed.
2 drops of CaCl2 Solution acid But Soluble in dil. HCl (water soluble)

 Preparation of Derivative
12
 Amide Derivative
Heat 0.5 gm of Acid with 1 gm of PCl5 or 2 ml of Thionyl chloride in a china dish, cool and add to it
few drops of conc, ammonia. Filter the solid so formed, wash it with water, then with sodium
bicarbonate solution and finally with water. Recrystallise from alcohol. Dry and determine its
melting point.
Amide derivative of Salicyaldehyde (Salicyamide) M.P.= 1350C
Amide derivative of Benzoic acid (Benzamide) M.P.= 1280C

Reactions -
PCl5/
R-COOH R-COCl + NH3 R-CO- NH2
SOCl2
ACID ACID CHLORIDE AMIDE

 Anilide Derivative
Heat 0.5 gm of Acid with 1 gm of phosphorus pentachloride (PCl5) or 2 ml of Thionyl chloride
(SOCl2) to prepare acid chloride in a test tube. The acid chloride is treated with 1 ml of aniline in
benzene. The mixture is warmed carefully in a water bath. Cool and filter the solid, wash with dil.
HCl to remove excess of aniline. Wash the solid with water. Recrystallise from alcohol. Dry and
determine its melting point.
Benzanilide - M.P. 1640C.
Reactions-
PCl5 C6H5-NH2
R-COOH R-COCl R-CO- NH-C6H5

ACID ACID CHLORIDE ANILIDE

 Dibromo Derivative of Cinnamic acid (Cinnamic acid dibromide)-

Dissolve about 0.5 gm of Cinnamic Acid in 5 ml of glacial acetic acid. Add 5 ml of 5% bromine in
acetic acid. Keep the reaction mixture for 10 minutes and pour this content into 20 ml of water. Filter
the precipitate, wash it with water. Recrystallise from alcohol. Dry and determine its melting point.
M.P. 1950C.
Reactions-
Br

COOH COOH
Br2
ACETIC ACID Br

CINNAMIC ACID 2,3-dibromo-3-phenylpropanoic acid

 Acid Derivative of Cinnamic acid (Benzoic Acid)-

Take about 0.5 gm of Cinnamic Acid and add about 5 ml of 10% sodium carbonate solution. Boil the
contents till Cinnamic acid dissolves. Cool and add about 20 ml of saturated KMnO4 solution.

13
 Reflux for 20 minutes and filter. Acidify the filtrate with conc. HCl, when benzoic acid precipitates.
Recrystallise it from hot water. Dry and determine its melting point. M.P. 1220C.
Reactions-

COOH COOH
10%
Sodium Carbonate
KMNO4

CINNAMIC ACID Benzoic acid

 Acetyl Derivative (Acetyl Salicylic Acid or Aspirin)-

Take about 0.5 gm of Acid; add 2 ml of acetic anhydride and 2 drops of conc. H2SO4. Heat the
contents for 5 minutes and pour this into 20 ml cold water. Filter the solid, wash it with water.
Recrystallise it from hot water. Dry and determine its melting point. M.P. 1350C.
Reactions-
O

COOH O
O
+ CH3-CO-O-CO-CH3 Conc.H2SO4

OH OH

Salicyalic Acid Acetic anhydride Aspirin

 5-Nitro Salicylic Acid-

Take about 0.2 gm of Salicylic Acid. Add 5 ml of water. Boil and then add 0.5 ml of conc. HNO 3.
Boil the yellow solution for 5 minutes and pour this into 20 ml of ice water. Filter the product and
crystallise it from hot water. Dry and determine its melting point. M.P. 2300C.
Reactions-
COOH
O2N COOH
Conc. HNO3

OH
OH
Salicyalic Acid 5-nitro Salicyalic Acid
 S- Benzylthiouronium salt of Acids
Dissolve 0.2 gm of carboxylic acid in 2-3 ml of hot water, add to it one drop of Phenolpthalein and
then dil. NaOH till just pink colour appears. Add to it very dil. (0.1N) HCl drop by drop till just pink
colour disappers and solution becomes just neutral. Now add 2 ml of aqueous solution of S-benyl-
iso-Thiouronium chloride and shake solution well. Solid separate out. Filter and recrystallize from
hot water.

14
 NH2 NH2

C6H5-CH2-S-C-NH2 Cl + RCOONa C6H5-CH2-S-C-NH2 COOR

 PHENOLS
Phenols containing C, H and (O) as the Elements-
Test Observation Inference
1. Compound + 10 drops of ethyl alcohol + Blue, Violet or Green Phenolic –OH group is
2-3 drops Neutral FeCl3 Solution. Colour. Present.

 Separation of Phenols:
C.T for α-Naphthol -
Test Observation Inference
1. 1 ml aqueous soln of Compound + 2 ml Violet Colour α-Naphthol is Confirmed
Bromine water + 1 ml of 10% NaOH
Solution.
2. Compound + Phthalic anhydride + 1 drop of Green Colour α-Naphthol is Confirmed
conc. H2SO4 and Heat, cool and pour this into
little NaOH Solution
3. Compound + NaOH Solution + 1 drop of Blue Colour α-Naphthol is Confirmed
CCl4. Add copper foils and warm

C.T for β-Naphthol -

Test Observation Inference
1. 1 ml aqueous soln of Compound + 2 ml Yellow Colour β-Naphthol is Confirmed
Bromine water + 1 ml of 2N NaOH Solution.
2. Compound + Phthalic anhydride + 1 drop Faint Green Colour β-Naphthol is Confirmed
of conc. H2SO4 and Heat, cool and pour this
into little NaOH Solution
3. Compound + NaOH Solution, heat to Blue Colour β-Naphthol is Confirmed
dissolve. Add CHCl3 and warm

C.T. for Resorcinol –

Test Observation Inference
1. Compound + Phthalic anhydride + 1 drop Yellowish red Resorcinol is Confirmed
of conc. H2SO4 and Heat, cool and pour this Solution with green
into little NaOH Solution fluorescence

Preparation of Derivative-
 Acetyl derivative:
Take about 0.5 gm of phenol; add 2 ml of acetic anhydride and 2 drops of conc. H2SO4. Heat the
contents for 5 minutes and pour this into 20 ml cold water. Filter the solid, wash it with water.
Recrystallise it from minium amount of alcohol.

15
 OH O
COCH3
H2SO4
+ CH3- CO O + CH3COOH
2

Phenol Acetyl derivative

of phenol
 Picrate Derivative (Picrate of α-Naphthol / β-Naphthol )
Take about 0.5 gm of phenol 10 ml of benzene or alcohol. Add to it saturated solution of picric acid
in benzene or alcohol and shake well. The orange coloured precipitate separates out. Filter, dry and
determine its melting point.
Picrate of α- Napthol M.P.= 1890C.
Picrate of β- Napthol M.P.= 1560C
Reactions-
OH OH OH
OH
O2N NO2 O2N NO2

NO2 NO2
Phenol Picric Acid Picrate of Phenol

 Benzoyl Derivative (α-Naphthyl benzoate / β-Naphthyl benzoate)-

Dissolve about 1 gm of phenol in 10-15 ml of 10% NaOH solution in a small conical flask. Add
about 2 ml of benzoyl chloride slowly and cork the conical flask immediately. Shake vigorously for
10 minutes. Cool and filter the precipitate, wash it first with dil. HCl and then with water.
Recrystallise the product from alcohol. Dry and determine its melting point.
M.P. of α-Naphthyl benzoate = 560C.
M.P. of β-Naphthyl benzoate = 107oC
Reactions-
OH O COC H
6 5
+ C6H5- CO-Cl 10% NaOH

Phenol phenyl benzoate

 3,5- Dinitrobenzoate Derivative (Chloro Phenol)

Transfer the 3,3-dinitrobenzyl chloride to a test tube. Add 1 ml of phenol, cork the tube loosely and
heat on boiling water bath for 20 min. Cool the mixture , add saturated solution of sodium hydrogen
carbonate solution, break up the resulting solid ester with a stirring rod and filter the ppt. wash with
water. Record the melting point.

16
 COCl COOAr

+ Ar- OH
+ HCl
O2N NO2 O2N NO2

 AMINES
Amines containing C, H, (O) and N as the Elements-
Test Observation Inference
Diazotisation Test
1. Compound + dil. HCl, and cool, and Orange-red dyestuff Aromatic –NH2 group is
add NaNO2 sol . Cool add this to the β-
n
Present.
Naphthol NaOH Soln (Primary amine)
2. Compound + dil. HCl, boil and cool, a)Yellow solid precipitate at Aromatic ›NH group is
and add ice cold NaNO2 soln. top of tube Present.
(Secondary amine)
b)Red colour solution and on
addition NaOH green solute Tertiary amine present
appears
3. a) 10 mg substance + 1 ml of 50% Black or Gray ppt Nitro aniline present
alcohol + 6 drops of CaCl2 + pinch of
Zn dust. Heat to boil and filter into 1 ml
tollen’s reagent.

b)Compound + FeSO4 solution + Reddish-brown precipitate –NO2 group is Present.

NaOH Soln and boil

 Confirmatory Tests-
C.T for p-Toluidine -
Test Observation Inference
1. Compound + 50% H2SO4 + HNO3. Blue Colour p-Toluidine is Confirmed.
2. Compound + 50% H2SO4 + K2Cr2O7 Yellow Colour p-Toluidine is Confirmed.
Solution.
3. Compound + 1 drop of dil. HCl + 2 Pale yellow colour changes p-Toluidine is Confirmed
drops of aqueous FeCl3 to blue

C.T for p-Nitroaniline -

Test Observation Inference
1. Compound + NaOH Solution and Yellow or Brown Colour p-Nitroaniline is Confirmed.
Shake well.
2. Compound + Zn dust + dil. HCl and Green colour changes to p-Nitroaniline is Confirmed.
shake. Allow to stand for 5 minutes. reddish brown
Filter and add NaNO2 solution.

C.T for Diphenylamine -

Test Observation Inference
1. Compound + dil. HCl, cool and add Yellow oil or solid Diphenylamine is
17
 NaNO2 solution Confirmed.
2. Compound + conc. H2SO4 + 1 drop Deep blue colour Diphenylamine is
of NaNO2 Solution. Confirmed.
3. Compound + conc. HCl + HNO3. Blue colour Diphenylamine is
Confirmed.

 Preparation of Derivative-
 Acetyl Derivative -
Heat 0.5 gm of aniline with 1 ml of acetic anhydride. Pour it into water. Filter the product, wash it
with water. Recrystallise from alcohol. Dry and determine its melting point.
Acetyl Derivative of p-Toluidine - M.P. 1480C.
Acetyl Derivative of Diphenylamine – M.P. 1010C.
Acetyl Derivative of nitroaniline - M.P. 2150C
Reactions-
H
NH2 N
COCH3
H2SO4
+ CH3- CO O + CH3COOH
2

Aniline N-phenylacetamide
 Benzoyl Derivative -
Take 0.5 gm of aniline + 3 ml of acetone + 1 ml of benzoyl chloride shake well and pour into cold
water. Filter the solid and crystallise it from aqueous alcohol. Dry and determine its melting point.
Benzoate of p-Toluidine - M.P. 1580C.
Benzoate of Diphenylamine - M.P. 180oC
Benzoate of Nitroaniline - M.P. 199oC
H
NH2 N
COC6H5
Acetone
+ C6H5- CO-Cl

Aniline Benzoate Derivative

Reactions-
Picrate derivative for tertiary amines only
Take about 0.5 gm of substance in 10 ml of benzene. Add to it saturated solution of picric acid in
benzene 2-3cc and shake well till precipitate separates out. Filter, dry and determine its melting
point.
H3C CH3 H3C CH3 OH
N OH N
O2N NO2 O2N NO2

NO2 NO2
Tertiary Amine Picric Acid Picrate of Ter. Amine

4. NEUTRAL COMPOUNDS
18
 Neutral Compounds containing C, H and (O) as the Elements-
Test Observation Inference
1. Compound + Alcohol + No Orange precipitate ›C=O group is Present.
2, 4-DNP Solution.
2. Take 2 ml schiff’s reagents in a test Pink colour (at the bottom) Aromatic aldehyde (Ar-CHO)
tube & add 2, 3 drop of the substance & slowly develops on standing present.
keep it.
3. 2 ml tollen’s reagent+ 2, 3 drop of Silver gates deposited on the Aldehyde group is present
substance shek well and then warm inner walls of the test tube
carefully (Silver mirror is formed)
4. 2 drops of substance+ 2 ml fehlings Red PPT of Cu2 O Aldehyde group present
solution (A+B equal amount) & warm
carefully
5. 2,3 drop of substance + 5 drop of Red Colour Ketonic Group is present
sodium nitroprusside + NaOH Shake
6. 2, 3 drop of substance + 5 drop of 2,4 Yellow or Red PPT Ketonic group is present
DNP reagent shake
7. 2, 3 drop of substance + 1 ml water + 1 Pink colour disappears after Ester group is present
drop of phenolphthalein + dil. NaOH till heating
a pink colour appears then heat
8. 2, 3 drop of substance + 1 ml of Red violet colour Ester group is present
alcoholic hydroxylamine hydrochloride
solution + NaOH (till alkaline) heat to
boil cool and neutralized by dil. HCL
then add 2, 3 drop of FeCl3
9. 5, 6 drop of substance in a dry test tube Evolution of H2 gas Alcohol group is present
+ a piece of dry sodium metal and close
the mouth of the thumb

Conclusion: - The functional group present is ------------

Preparation of Derivative
1) 2,4-dinitro phenyl hydrazine (DNP) for Aldehyde and Ketone
Take 2 mg of substance in test tube and dissolve it in 2 ml of ethyl alcohol. Now add 2,4 dinitrophenyl
hydrazine reagent about 2-3 cc and shake the reaction mixture for 10 minutes, solid separated out.
Recrystilises product from ethanol or acetone or ethyl acetate.
NO2 R NO2

H2N-N C NNH
EtOH
R- CHO + H
NO2 NO2

Aledehyde 2,4-DNP 2,4-dinitro phenyl hydrazone

19
 NO2 R NO2
R
H2N-N C NNH
O + EtOH
R
R NO2 NO2

Ketone 2,4-DNP 2,4-dinitro phenyl hydrazone

2) Acetyl derivative of Alcohol:

Take 0.5 gm of substance in dry test tube and add in it 1-2 ml of acetic anhydride. Then add 2-3 drop of
pyridine and reflux for 2-3 min. Pour it into water. Filter the product, wash it with water. Recrystallise
from alcohol. Dry and determine its melting point.

R- OH + CH3- CO O Pyridine
R- O-CO- CH3 + CH3COOH
2
Alcohol Acetic anhydride Acetyl Derivative Acetic acid
Carbohydrate

Test Observation Inferences

Comp.+1 ml H2O+2,3 drops 10% ἀ– Reddish Violet Colouration at Carbohydrates present.
Naphthol in alcohol+1 ml Conc. H2So4 the Junction of two layer

Derivatives:
1) Osazone derivative: Take in test tube 0.2 gm carbohydrate and add to it one gram of crystalline sodium
acetate and 1 gm of phenyl hydrazine hydro chloride dissolve in 5 cc of water. Now add one ml of
saturated solution of sodium bisulphate, shake the solution and keep test tube in beaker of boiling water.
The osazone derivative separate out. Filter the products and record the melting point.
Reaction:
O
C- H H -C N-NH Ph

H C OH Sodium acetate C N NH Ph
+ 3 Ph-NH-NH2
(CHOH)3 Ethanol (CHOH)3

CH2OH CH2OH

Glucose Osazone
2) Acetyl derivative:
Take 0.5 gm of carbohydrate in dry test tube and add to it 0.5 gm of fused sodium acetate and 5 ml of
acetic anhydride. Then reflux for 5-10 min. and then Pour it into cold water. Filter the product, wash it
with water. Recrystallise from alcohol. Dry and determine its melting point.
Reaction:

20
 O
C- H H -C O

+ CH3- CO O HO C COCH3
(CHOH)4 2 4
CH2OCOCH3
CH2OH

Glucose Acetic anhydride Acetyl Derivative

 If all above test are absent then Hydrocarbon are present.
Confirmatory Tests-

Test Observation Inference

1. Dissolve 0.5gm of Compound in 2ml of a)Yellow precipitate Naphthalene is Confirmed
benzene + 1 ml picric acid in benzene and
shake well. Anthracene is confirmed
b) orang precipitate
2. Compound + CHCl3 + AlCl3 and Heat, Green Colour Naphthalene is Confirmed
cool and pour this into little NaOH
Solution
3. 0.5gm of Compound + 2 ml glacial Yellow precipitate Naphthalene is Confirmed
acetic acid + 1 ml nitrating mixture. Warm,
cool and pour this contents into the water

Preparation of Derivative
 Picrate Derivative
In a dry test tube, dissolve about 1 gm of compound in 10 ml of benzene, add to it saturated solution
of picric acid in benzene and shake well. The yellow coloured precipitate separates out. Filter the
precipitate. Recrystallise the product from alcohol. Dry and determine its melting point..
Picreate of Napthalene - M.P. 1500C
Picreate of Anthracene - M.P. 1380C
Reaction-
OH
H OH H
O2N NO2 O2N NO2

NO2 NO2
Hydrocarcons Picric Acid Picrate of Hydrocarbons

 Nitro Derivative
In a 100 ml conical flask, take about 1 gm of compound and add to it 10 ml of fuming nitric acid.
Heat the contents for 5 minutes. Cool and add 1 full test tube of cold water and shake vigorously.
Filter and wash it with cold water. Dry and determine its melting point.
Nitro derivative of Napthalene - M.P. 610C.
21
 Reaction-
NO2
Conc. HNO3
Conc. H2SO4

Hydrocarcons 1-Nitro napthalene

 Neutral Compounds containing C, H, (O) and N as the Elements-

Test Observation Inference
1. Compound + dil. H2SO4, boil and cool + –NHCOR group is Present.
NaNO2 soln. Cool add this to the β- Orange-red dyestuff
Naphthol NaOH
2. Compound + FeSO4 solution + NaOH Reddish-brown precipitate –NO2 group is Present.
Soln and boil
3. Compound + Acetone + NaOH solution Red or Violet Colouration m-dinitro compound is present
4. Compound + 1 ml 50 % alcohol + 6 Black or Gray PPT NO2 group is present
drop CaCl2 + Pinch of Zinc Dust heat to
boil and filter into 1 ml tollen’s reagent
5. Compound + 1 ml NaOH boil Evolution of NH3 gas which Amide is present
turns termaric paper red
6. Compound + 5 drop conc. HCl boil and Orange Dye Stuff Anilide group is present
Cool in ice water + excess of NaNO2
solution and above solution into 1 ml ice
cold solution of of Ᏸ- naphthol in NaOH

5. Confirmatory Tests-
C.T for m-Dinitrobenzene -
Test Observation Inference
1. 1 gm of Compound + 1 ml of NaOH Red-brown colour m-Dinitrobenzene is
solution and heat. Confirmed
2. Compound + NaOH solution and boil. Violet Colour m-Dinitrobenzene is
Add traces of SnCl2 Confirmed

C.T for Acetanilide -

Test Observation Inference
1. 0.2 gm of Compound + 5 ml of conc. Rosy or Purple colour Acetanilide is Confirmed
H2SO4 and shake to dissolve. Add solid
K2Cr2O7 and Shake well.

Preparation of Derivative-
 Nitroaniline Derivative (m-Nitroaniline) by partial reduction -
Dissolve about 1 gm of m-Dinitrobenzene in 20 ml of ethyl alcohol. Add to it 1 ml of conc.
Ammonia solution. Pass H2S gas in it for 5 minutes. Heat the contents for 5 minutes, add dil. HCl,
dilute with water and filter. Add ammonia solution or NaHCO3 solution to the filtrate to make it

22
 alkaline. Filter the precipitate, wash it with water. Recrystallise the product from hot water. Dry and
determine its melting point. M.P. 1140C.
Reactions-
NO2
NH2

NH4OH
H2S
NO2
NO2
1,3-dinitrobenzene
3-nitrobenzenamine
Acetanilide-
 Bromo Derivative (p-Bromo Acetanilide) -
Dissolve about 1 gm of Acetanilide in 5 ml of glacial acetic acid. Add 5 ml of 5% bromine in acetic
acid. Keep the reaction mixture for 5 minutes and pour this content into 20 ml of water. Filter the
precipitate, wash it with water. Recrystallise from alcohol. Dry and determine its melting point. M.P.
1670C.
Reactions-
NHCOCH3 NHCOCH3

Br2

CH3COOH

Br
N-phenylacetamide N-(4-bromophenyl)acetamide

 Nitro Derivative (p-Nitro Acetanilide) -

Take about 0.5 gm of Acetanilide, add 2 ml nitrating mixture at 0-50C and shake carefully. Pour the
contents in ice cold water. Filter the contents, wash it with cold water. Recrystallise from alcohol.
Dry and determine its melting point. M.P. 2160C.
Reactions-
NHCOCH3 NHCOCH3

HNO3 + H2SO4

o
0-5 C

NO2
N-phenylacetamide N-(4-nitrophenyl)acetamide

Derivative of Urea (Amide)

Nitrate of Urea: Dissolve (0.5 g) urea in water (4ml) & add Conc. HNO3 (1ml) with stirring filter
the urea nitrate and determine the M.P.
Reaction:

23
 NO3
O H
+ O
HNO3
H2 N NH2
H2N NH2
Urea Urea Nitrate
Oxalate of Urea: Dissolve (0.5 g) urea in water (4ml) & add soln of oxalic acid (0.6 g in 8 ml water)
mix well. Filter the urea oxalate & determine the M.P.

Substance containing C, H, (O), N and S element

Test Observation Inference
1. Compound fuse in a test Blood Red Colour Thiourea present
tube cool + 1 ml water + 2
drop FeCl3

Substance contaning C, H, (O) and Halogen elements

Test Observation Inference
1. Compound + 1 ml NaOH a) White PPT settles at the bottom Aliphatic halide present
boil and Cool add 5, 6 drop b) No White PPT
of conc. HNO3 + 2 drop Aromatic Halide present
AgNO3 Shake well

Conclusion: - The compound contains ----------------- as the Functional Group(S).

Derivative of Thiourea and aliphatic or aromatic halide

S-Benzylsothiouronium Chloride: Place a mix. Of 0.5 g of finely powdered thiourea and 0.5 g of
alkyl halide and 5 ml of ethanol in test tube and reflux 10-20 min. Then add 0.5 g of picric acid, boil
until a clear solution is obtained and cool. If ppt not form then add water. Recrystallise the resulting
S-alkyl isothiouronium picrate from ethanol. M.P. 188oC

S NH
HOC6H2(NO2)3
+ X
R- X R-S-C
H2N NH2
NH2
Thiourea Alkyl halide S-alkylisothorium halide salt
NH2
OC6H2(NO2)3
R-S-C
NH2

S-alkylisothorium Picrate

Nitro Derivative of Aromatic halide:

24
 Add 1 g of compound to 4 ml conc. H2SO4 and cautiously introduce drop by drop 4 ml conc. HNO3.
Warm the mix on water bath for 10 min. then pour it on crushed ice. Collect the ppt recrestlises from
ethanol. Determine the M.P.
X X

NO2
Conc. H2SO4
Conc. HNO3

NO2

 Result: Binary / Ternary Mixture-

Steps Component I Component II (Or) Component III
 Nature
 Type
 Elements
 Functional group(s)
 Physical Constant
 Name of Compound
 Molecular formula Of Compound
 Structure Of Compound
 Derivative Of Compound
 Physical constant of derivative
 Structure of derivative

Compounds for Reference

COMPOUND STRUCTURE CHARACTERISTICS DERIVATIVE

Carboxylic acids CH2COOH White Crystalline Solid Anilide 118 0C
Phenyl acetic acid Perfume like Smell Sparingly S-Benzyl 160 0C
M.P. 76 0C Soluble in water

Oxalic acid HO O Soluble in water, insoluble in Anilide 245 0C

(Dihydrate) 102 0C either, white crystalline S-Benzyl 195 0C

O OH
Benzoic acid HO White crystalline solid, soluble Anilide 162 0C
M.P. 101 0C in hot water, alcohol Benzene B-Benzyl 166 0C
etc.
O

25
Cinnamic Acid HO Cream coloured shining Dibromoderivative
M.P. 133 0C crystals sparingly soluble in 195 0C
water soluble in alcohol S-Benzyl 175 0C
O

Adipic acid O OH Colourless crystalline solid Anilide 239 0C

O
M.P. 151 0C soluble in water S-Benzyl 159 0C

OH
Sallicylic acid HO Colorless needle shaped Aspirin 135oC
M.P. 158 0C crystals soluble in hot water, Nitro derivative
HO
gives violet colour with aq. 230oC
Ferric chloride solution

O
Anisic acid HO Crystalline colourless solid, Anilide 171 0C
M.P. 184 0C soluble in cold water, soluble S-Benzyl 185 0C
O
in hot water
O
Succinic acid O Colourless crystalline solid, Anhydride 119 0C
M.P. 185 0C soluble in water and alcohol, S-Benzyl 149 0C
OH insoluble in either
HO (gives phthalein test)

O
Phthalic acid White crystalline solide, Anhydride 135 0C
M.P. 195-235 0C OH soluble in hot water, sparingly S-Benzyl 157 0C
soluble in ether, mix 0.2 gm of
O
acid with 0.4 gm of resorcinol
and 0.5 ml of Conc. H2SO4.
HO
Heat gently until mixture turns
red brown, cool & Pour in
water and add 1 ml of NaOH
O Orange green fluorescence is
formed (Phthalein test)
P-Hydroxy Benzoic O White needle shaped crystals Anulide 197 0C
acid sparingly soluble in water no Acetate 187 0C
OH
M.P. 219 0C colour with aq. FeCl3 S-Benzyl 143 0C
HO
M-Nitrobenzoic acid O Pale yellow, crystalline solid Anilide 151 0C
M.P. 141 0C sparingly soluble in cold water S-Benzyl 159 0C
NO2 soluble in hot water
HO

26
O-Nitrobenzoic acid O2N Pale yellow crystalline solid Anilide 155 0C
soluble in hot water, when S-Benzyl 159 0C
O heated with solalie form Nitro-
benzene with odour of bittle
almonds.
HO
M-Chlorobenzoic acid Cl White crystalline solid soluble Amide 134 0C
M.P. 158 0C in hot water S-Benzyl
O

HO
O-Chlorobenzoic acid Cl White crystalline solid soluble Anilide 114 0C
M. P. 140 0C in hot water S-Benzyl
O

HO
P-Chlorobenzoic acid O White crystalline solid, Anilide 114 0C
M.P.230 0C Sparingly soluble in wter S-Benzyl 186 0C
Cl soluble in hot water

HO

P-Nitrobenzoic acid COOH Pale yellow crystalline solid Anilide 211 0C

M.P. 240 0C sparingly solule in cold water S-Benzyl 180 0C
and benzene . When heated
with sodalime forms
Nitrobenzene with smell of
bitter almonds.

NO2
O-Aminobenzoic acid H2N Crystalline solid, Soluble in Bromo 227 0C
M.P. 144 0C water, with bromine in acetic Acetyl 185 0C
O acid yields 3;5 dibromo
derivative.

HO
M-Amino benzoic acid NH2 Soluble in hot water, Acetyl 250 0C
M.P. 174 0C crystalline solid fusion with Benzal 119 0C
O
Zink chloride, yields violet
product giving brown solution
in alcohol
HO

27
P-Aminobenzoic acid O Crystalline solid, soluble in hot Acetyl 252 0C
M.P. 186 0C water Benzal 193 0C
NH2

HO

Hippuric acid O Crystalline solid, soluble in hot Benzoic acid 121 0C

M.P. 190 0C water on boiling with HCL
OH yields benzoic acid
Ph N M.P. 121 0C
H

PHENOLS
COMPOUND STRUCTURE CHARACTERISTICS DERIVATIVE
Phenol Colourless solid or slightly Benzoate 68 0C
B.P. 181 0C pinkish solid violet colour with
aq. FeCl3, in water. Warmed with
HO phthalic anhydride & a drop of
conc. H2SO4, when solution made
slightly alkaline give red colour
(Phthali test)
O-Cresol Colourless liquid violet color with Bromo 56 0C
B.P. 196 0C aq. FeCl3 with aq. Bromine in
excess gives bromo derivative
HO
Warmed with phthalic anhydride
and a drop of conc. H2SO4, Yield
red colour with alkaline solution
Salicylaldehyde HOC Colourless liquid insoluble in 2,4 DNP 252 0C
B.P. 196 0C water, soluble in organic solvents,
gives violet colour with FeCl3
(alcoholic)
HO

M-Cresol Colourless liquid, Blue-Violet Benzoate 54 0C

B.P. 202 0C colour with aq. FeCl3 Bromo 84 0C

OH
P-Cresol Colourless liquid, Blue colour Benzoate 71 0C
B.P.202 0C with FeCl3 in water, with excess
HO
of bromine water yields bromo
derivative.

28
O-Chlorophenol Cl With Nitric acid in acetic acid, 3,5-
B.P. 175 0C yield Dinitro derivative Dinito
0
M.P. 111 C benzoate
1430C
HO

P-Chlorophenol On adding conc. Nitric acid,yield 3,5-

B.P. 217 0C dintroderivative Dinito
HO Cl
M.P. 81 0C benz ate
1860C
ἀ-Naphthol OH Pale brown colour, very faint pink Benzoate 56 0C
M.P.94 0C colour when pure no colour with
FeCl3 in Water but white ppt
Wrmed with CCl4 + Cu powder
gives jblue colour.

Catechol HO White crystalline solid gives Dibenzoate 84 0C

M.P. 104 0C green colour with FeCl3

HO

Resorcinol Pinkish white crystalline solid Benzoate 117 0C

M.P. 110 0C soluble in water, ether alcohols
Gives blue violet colour with
FeCl3 substance and phthalic acid
in 2:1 ratio & one ml of conc.
H2SO4 heat gently and then
HO OH strongly pour content in very dil
NaOH solution. Gives yellow
green fluorescence
Ᏸ-Naphthol OH Pale pink, solid White crystalline Benzoate
M.P. 122 0C when pure state. Insoluble in 107 0C
water

Hydroquinone Soluble in water, insoluble in Diacetate

M.P. 169 0C HO OH benzene transtent blue colour 133 0C
with FeCl3 in water.
O-Nitrophenol OH Bright yellow solid, sweet smell, Dibromo
M.P. 45 0C sparingly soluble in cold water 117 0C
O- giving yellow colour soluble in
hot water soluble in NaOH giving
N+ orange red colour
O

29
 M-Nitrophenol HO Pale yellow crystalline solid Bromo 91 0C
M.P. 97 0C odourless, soluble in hot water, Bebziate 95 0C
O- soluble in NaOH to produce
orange yellow colour
N+

O
P-Nitrophenol O Colourless crystalline solid, Dibromo 142 0C
M.P. 114 0C soluble in NaOH giving bright Benzoate 142 0C
N+ OH yellow colour
-
O

AMINES
Primary amines
COMPOUND STRUCTURE CHARACTERISTICS DERIVATIVE
Aniline NH2 Light straw colour soluble in ethyl Acetate 114 0C
B.P. 184 0C alcohol-potassium dichromate ( Benzoate 164 0C
0.2 gm) and conc. H2SO4 about 1
ml add one drop of aniline a blue
or black colour is obtained
O-Toludine Colourless liquid red brown Acetate 112 0C
B.P. 200 0C NH2 colour on exposure to air and light Benzoate 114 0C
dissolve small amount of
substance in H2SO4 and add pinch
of K2 Cr2 O7. A blue colour is
obtained which changes to purple
on dilution with water
M-Toludine Colourless liquids, develops pink Acetate 660C
B. P. 203 0C H2N kbrown colour on exposure to air. Benzoate 1250C
Dissolve small amount of
substance in conc. H2SO4 and &
add to it pinch of K2 Cr2 O7., a
yellow brown colour is obtained
which change to red on addition of
HNO3
O-Chloroaniline Cl Colourless liquid, soluble in Acetate 880C
B.P. 2090C organic solvents. Benzoate 990C

H2N

O_Anisidine NH2 Colourless liquid on exposure to Acetate 880C

B.P. 2250C air develops dark coloured liquid

30
M-Chloro aniline Colourless liquid soluble in Benzoate 1220C
B.P. 2300C organic solvents

Cl NH2

M-Anisidine Colorrless liquid soluble in Acetate 800C

B.P. 2510C organic solvents

O NH2
P-Toludine Colorless solid, it has Acetate 154 0C
B.P. 48 0C characteristic odour, sparingly Benzoate 158 0C
soluble in water, soluble in
organic solvents. Dissolve
substance in 1 ml of H2SO4 Divide
H2N solution in two parts to one part
add a pinch of K2 Cr2 O7 & Shake
yellow colour formed to second
portion add dil HNO3 Blue colour
changes to violet to red to brown
is formed.
α- Naphthyl Amine NH2 Crystalline dark brown black
M.P. 50oC colour solid, unpleasant odour Acetate 160 0C
insoluble in water, soluble in Benzoate 161 0C
organic solvents.

P-Anisidine Crystalline colourless solid Acetate 130 0C

M.P. 57 0C develops dark colour on keeping Benzoate 154 0C
H3CO NH2 sparingly soluble in hot water
little substance add 2-3 ml of dil
HCl & two drops of aq FeCl3
violet colour is formed
P-Chloro aniline Colourless crystalline solid, Acetate 1790C
M.P. 700C soluble in organic solvents Benzoate 1930C
H2N Cl

O-Nitro Aniline NH2 Golden yellow or orange coloured Acetate 940C

M.P. 710C solid, soluble in hot water gives Benzoate 980C
O pale yellow colour to water
N+

O-

31
ß-Naphthyl amine NH2 Pink colour crystalline solid Acetate 1340C
M.P. 1130C sparingly soluble in hot water Benzoate 1620C
gives no colour to FeCl3 solution

M-Nitro Aniline H2N Yellow crystalline solid soluble in Acetate 1550C

M.P. 1140C O
hot water gives pale yellow colour Benzoate 1990C
to water
N+

O-

P-Nitro Aniline -
O Yellow solid soluble in hot water Acetate 2160C
M. P. 1480C & organic solvents gives pale Benzoate 1990C
N+ NH2
yellow colour to water
O
Secondary Amines Colourless liquid insoluble in Acetate 1030C
N-Methyl Aniline HN
water, soluble in organic solvent
B.P. 1480C

N-Ethyl Aniline Colourless liquid insoluble in Acetyl 550C

B.P. 2050C water, but soluble in organic Benzoate 600C
HN solvent

Diphenyl Amine Pale pink crystalline solid, Acetyl 1030C

M.P. 540C insoluble in water soluble in Benzoate 1800C
alcohol
N
H

Tertiary Amine
Colourless liquid insoluble in Picreate M.P. 164oC
N
N.N-Dimethyl water but soluble in organic
Aniline solvents.
B.P. 1930C

CARBOHYDRATES CHO White crystalline solid soluble in Osazone 2050C

D-Glucose water and hot alcohol insoluble in Penta acetate
H OH
M.P. 1460C benzeneand either 1120C
HO H

H OH

H OH

CH2OH

32
D-Fructose O OH HO
White crystalline solid, soluble in Osazone 2050C
M.P. 1460C water, insoluble in alcohol,
HO
benzene and ether
HO OH
Maltose (Hydrated) OH OH White crystalline solid soluble in Osazone 2500C
M.P. 1000C HO O OH water Insoluble in alcohole Octa acetate 1580C
benzene and ether
O
HO O OH

OH
HO
Sucrose Cane sugar HO
OH
White crystalline solid soluble in Octa acetate 690C
C12H22O11 cold water Insoluble in benzene &
HO ether, sparingly soluble in alcohol
OH on reaction ppt with phenyl
O
O hydrazine of fehling solution after
HO hydrolysis (i.e. wanning with HCl)
O it reduces fehling solution & react
OH
HO with phenyl hydrazine
HO

CARBONYL O Colorless liquid, has smell of 2,4 –DNP

COMPOUNDS bitter almonds, insoluble & M.P. 2370C
ALDEHYDES heavier than water, soluble in
Benzaldehyde organic solvents. It does not
B.P. 1790C H reduce fehling’s solution
Salicylaldehyde HO Colorless liquid, Sparingly soluble 2,4 DNP
B.P. 1970C H
in water, gives violet colour with 2310C
aqueous FeCl3

O
Anisaldehyde Colourless liquid insoluble in 2,4 DNP
B.P. 2480C water 2540C
HOC OCH3

Vanillin HO Colorless crystalline solid 2,4 DNF

M.P. 810C sparingly soluble in water, vamlla 2690C
smell
O
O

Ketones Colourless liquid has 2,4-DNP

O characteristic pleasant smell gives 128 0C
Acetone
M.P. 560C iodoform test. Compound +3,4
drops of iodine, then NaOH drop
to solution & on warming the
brown colour of iodine disappears
33
 & yellow ppt of iodoform forms &
have characteristic smell of
iodoform
Ethyl Methy CH3 CO C2 H5 Colourless liquid soluble in water 2,4- DNP
Ketone O alcohol &ether has pleasant smell 1150C
B.P.. 800C give iodoform test

Acetophenone O Colourless liquid has 2.4-DNP

B.P.2020C characteristic sweet smell M.P. 2380C
sparingly soluble in water soluble
in organic solyentsgives iodoforn
test
Benzil O Pale yellow crystalline solid very 2,4- DNP
M.P. 950C sparingly soluble in water M.P. 189oC
O

Anthraquinone O Pale yellow crystalline solid very Diacetate

M.P. 289oC C sparingly soluble in ether & M.P. 2600C
Benzene

C
O

HYDROCARBONS Colourless Mobile liquid with M- dinitro benzene 89

Benzene characteristic aromatic odour, 0C
B.P.800C insoluble in water miscible with
alcohol etc.

Toluene Colourless mobile liquid with 2.4- Dinitro

B.P.1100C benzene like odour, insoluble in 710C
water but miscible with organic
solvents.
Ethyl benzene Colourless mobile liquids with 2,4,6- Trinitro
B.P.1360C benzene like odour insoluble in 37oC
water miscible with organic
solvents.
P-Xylene Colourless liquid with 2,3,5- Trinitro
B.P.1380C characteristics aromatic odour 139oC
insoluble in water but soluble in
alcohol and ether.

34
M-Xylene Colourless liquid with benzene 2,4,6- Trinitro
B.P.1390C like odour insoluble in water but 182oC
miscible with orgnic solvents.

O-Xylene Colourless mobile liquid with 4,5- Dinitro

B.P.1440C benzene like odour insoluble in M.P. 71oC
water but soluble in organic
solvents.

Biphenyl White crystalline solid with 4,4’- Dibromo

M.P.700C characteristic aromatic odour M.P. 164oC
insoluble in water but soluble in Dinitro
alcohol and ether. M.P. 164oC

Naphthalene White crystalline solid with Picrate

M.P.800C aromatic odour insoluble in water M.P. 150oC
but soluble in organic solvents .
dissolve 0.019 ml of substance in
CHCl3 & few crystals of
anhydrous AlCl3 a green colour
develops
Anthracene Colourless solid with faint Picrate
M.P.2170C aromatic odour insoluble in water 1380C
but soluble in organic solvents

NITRO Pale yellow liquid with odour of M-dinitrobenzene

HYDROCARBONS bitter almonds insoluble in water 900C
Nitro benzene but miscible in organic solvents.
B.P.2090C
O2N
P-Nitrotoluene Pale yellow crystalline solid Nitro derivative
M.P.540C insoluble in water but soluble in 540C
organic solvents.
O2N
2,4-Dinitrotoluene Yellow coloured solids sparingly Nitro derivative
M.P.710C soluble in cold alcohol and ether 710C
soluble in benzene.
O2N NO2
M-Dinitrobenzene Pale yellow crystalline solid M-nitroaniline
M.P.90 0C insoluble in water but soluble in 1140C
organic solvents.
O2N NO2

35
HALOGEN Colourless liquid with pleasant 2,4- Dinitro
HYDROCARBONS smell insoluble in water but 520C
Cl
Clorobenzene soluble in organic solvents.
B.P. 1320C
Bromo Benzene Yellow colour liquid with pleasant 2,4- Dinitro
B.P. 1550C smell. Soluble in organic solvent 750C
Br
but insoluble in water

P-Dichlorobenzene White crystalline solid with 2-Nitro derivative

M.P. 520C Cl Cl chacteristic smell insoluble in 520C
water soluble in organic solvent.
ANILIDES AND White Crystal and solid soluble in Benzoic acid
AMIDES H2N hot water, alcohol and benzene, M.P. 1210C
Benzamide sparingly soluble in ether. Boil 0.1
M.P. 1290C gm substance in test tube add to it
1 ml NaOH Boil add HCL till
O
solution acidic white ppt of a
benzoic acid formed.
Urea NH2 Colour less crystalline solid Urea Nitrate
M.P. 1320C soluble in water insoluble in ether 1640C
H2N

O
Thiourea NH2 Colour less crystalline and solid S-benzylisothorium salt
M.P.1800C soluble in water insoluble in ether M.P. 1880C
H2N with aq. FeCl3 gives blood red Hydrochloride
colour
S
Acetanilide White Shining Crystals Soluble in Bromo
O
M.P. 1140C hot water. 1670C

N
H
Phenacetine Or White Crystalline Solid Slightly 3-Nitro
Soluble in Boiling Water Soluble 1030C
4-methoxyphenyl-acetamide H3COCHN OCH3 in alcohol.

M.P. 1340C

36

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