King Abdul Aziz University

Faculty of Science
Department of Chemistry
Organic Chemistry

Fundamental Organic Chemistry (I)

231
(Lab Manual)

Edited By:

Nada Tashkandi

Under supervision of:

Dr. Hamida Abdel Hamid

1428-1429H

1
 Safety Precautions

1-Safely Using Chemicals

When working with volatile materials, remember that heat causes

expansion, and confinement of expansion results in explosion. Remember
also that danger exists even though external heat is not applied.

Do not mix sulfuric acid with water inside a cylinder. The heat from the
reaction can break the base of the vessel because of the thickness of the
base and the seal.

Perchloric acid is especially dangerous because it explodes on contact with

organic materials.

Glass will be chemically attacked by hydrofluoric acid, hot phosphoric acid

and strong hot alkalis, so it should never be used to contain or to process
these materials.

Always flush the outside of acid bottles with water before opening. Do not
put the stopper on the counter top where someone else may come in contact
with acid residue.

Mercury is highly toxic. Special care is needed when dealing with mercury.

2-Identifying chemicals - DO NOT taste chemicals for identification.

Smell chemicals only when necessary and only by wafting a small amount
of vapor toward the nose.

3-Label with care - Never fill a receptacle with material other than that
specified by the label. Label all containers before filling.

4-Safely Handling Glassware

Handle glassware carefully. Hold beakers, bottles and flasks by the sides
and bottoms rather than by the tops. The rims of beakers or necks of bottles
and flasks may break if used as lifting points. Be especially careful with
multiple neck flasks.

2
5-Avoid Over Tightening Clamps - To avoid breakage while clamping
glassware, use coated clamps to prevent glass-to-metal contact, and do not
use excessive force to tighten clamps.

6-Safely Using Heat Sources

Be sure to check laboratory or instruction manuals when working with

heat sources.

7-Bunsen Burners
Adjust Bunsen Burner to get a large soft flame. It will heat slowly but also
more uniformly. Uniform heat is a critical factor for some chemical
reactions.

Adjust the ring or clamp holding the glassware so that the flame touches the
glass below the liquid level. Heating above the liquid level does nothing to
promote even heating of the solution and could cause thermal shock and
breakage of the vessel. A ceramic-centered wire gauze on the ring will
diffuse the burner flame to provide more even heat.

Rotate test tubes to avoid overheating one particular area. Uniform heating
may be critical to your experiment. Heat all liquids slowly. Fast heating
may cause bumping, which in turn may cause the solution to splatter. Do
not heat glassware directly on electrical heating elements. Excessive stress
will be induced in the glass, and this can result in breakage.

8-Hot Plates
Always use a hot plate larger than the vessel being heated. Thick-walled
items such as jars, bottles, cylinders and filter flasks should never be heated
on hot plates.

9-Evaporation
Evaporation work should be observed carefully. Be careful when handling a
vessel that has been heated after evaporation has occurred. It may crack
unexpectedly.

10-Heating Thick-Walled Vessels

Glassware with thick walls such as bottles and jars should not be heated
over a direct flame or comparable heat source.

11-Scratched Glassware
Do not heat glassware that is etched, cracked, nicked or scratched. It is
more prone to break.

3
 12-Mixing and Stirring
Use a rubber policeman on glass, or use Teflon rods to prevent scratching
the inside of a vessel. Do not look down into any vessel being heated or
containing chemicals. Do not point a vessel’s open end at another person. A
reaction may cause the contents to be ejected. Spattering from acids, caustic
materials and strong oxidizing solutions on the skin or clothing should be
washed off immediately with large quantities of water.

13-Pipetting

Do not pipet by mouth. For your safety, we suggest using a mechanical

pipetting device. Do not draw any liquids into a pipet by mouth. Serious
injury could result.

14-Vacuum and Pressure Warning

All glass containers used in vacuum work or which are under vacuum must
be securely and adequately taped or shielded to restrain flying glass in the
event of an implosion or other accident. Always wear safety glasses,
goggles, or a face shield.

Because of variations in conditions, Corning cannot guarantee any

glassware against breakage under vacuum or pressure. Adequate
precautions should be taken to protect personnel doing such work.

15- Ventilation

Always work in a well-ventilated area. When working with chlorine,

hydrogen sulfide, carbon monoxide, hydrogen cyanide and other very toxic
substances, always use a protective mask or perform these experiments
under a fume hood in a well-ventilated area. Cryogenic liquids should be
stored and handled in well-ventilated areas to prevent excessive buildup of
gas concentration. These should never be used in closed environmental
chambers

4
Some glassware used in lab:

Erlenmeyer Buchner Beaker

flask flask

Hirsch
Funnel
Buchner funnel
funnel

Stemless
Powder
funnel
funnel

Graduated Graduated
Pastur Pipit cylinder
Pipit

Round neck Round -3

bottomed bottomed flask
flask

5
 Wash bottle Support
stand

Spatulas Metal ring

figer clamp-3 Clamp

Condenser Drying tube

Clasien Stopper
adapter

Cork ring Screw clamp

6
 Distillation adapter
Separation funnel

Vacuum Distillation adapter

Distillation system

7
:Some important techniques
1-Crystallization

Crystallization is a technique which chemists use to purify solid

compounds. Crystallization is based on the principles of solubility:
compounds (solutes) tend to be more soluble in hot liquids (solvents) than
they are in cold liquids. If a saturated hot solution is allowed to cool, the
solute is no longer soluble in the solvent and forms crystals of pure
compound. Impurities are excluded from the growing crystals and the pure
solid crystals can be separated from the dissolved impurities by filtration.

How to do a crystallization

To crystallize an impure, solid compound, add just enough hot solvent is

added to it to completely dissolve it. The flask then contains a hot solution,
in which solute molecules – both the desired compound and impurities –
move freely among the hot solvent molecules. As the solution cools, the
solvent can no longer “hold” all of the solute molecules, and they begin to
leave the solution and form solid crystals. During this cooling, each solute
molecule in turn approaches a growing crystal and rests on the crystal
surface. If the geometry of the molecule fits that of the crystal, it will be
more likely to remain on the crystal than it is to go back into the solution.
Therefore, each growing crystal consists of only one type of molecule, the
solute. After the solution has come to room temperature, it is carefully set in
an ice bath to complete the crystallization process. The chilled solution is
then filtered to isolate the pure crystals and the crystals are rinsed with
chilled solvent.

2-Filtration

Filtration is a technique used either to remove impurities from an organic

solution or to isolate an organic solid. The two types of filtration commonly
used in organic chemistry laboratories are gravity filtration and vacuum or
suction filtration.

Gravity Filtration

Gravity filtration is the method of choice to remove solid impurities from

an organic liquid. The "impurity" can be a drying agent or an undesired side
product or leftover reactant. Gravity filtration can be used to collect solid
product, although generally vacuum filtration is used for this purpose
because it is faster.

A filtration procedure called "hot gravity filtration" is used to separate

insoluble impurities from a hot solution. Hot filtrations require fluted filter

8
paper and careful attention to the procedure to keep the apparatus warm but
covered so that solvent does not evaporate.

Vacuum Filtration

Vacuum filtration is used primarily to collect a desired solid, for instance,

the collection of crystals in a recrystallization procedure. Vacuum filtration
uses either a Buchner or a Hirsch funnel.Vacuum filtration is faster than
gravity filtration, because the solvent or solution and air is forced through
the filter paper by the application of reduced pressure. The reduced pressure
requires that they be carried out in special equipment:

 Buchner or Hirsch funnel

 heavy-walled, side arm filtering flask
 rubber adaptor or stopper to seal the funnel to the flask when under
vacuum
 vacuum source

9
 SATURATED AND UNSATURATED
HYDROCARBONS

Cyclohexane

Test Observation Result

Bromination-1 The colour of It is saturated

In two test tubes put bromine is not .compound
1ml of cyclohexane discharged from
+3ml of bromine with .the first tube
.will constant shaking The colour of the
Leave the first tube in second tube
light, expose the .disappears
second to sun light for
.15min Bromo -1
cyclohexane
Potasium -2 The violet colour It is saturated
Permanganate Test of the .compound
In a test tube Put 1ml Permanganate
of cyclohexane+ few .does not Change
drops of dil acidic
KMnO4 with shaking

10
 Cyclohexene

:Preparation of cyclohexene

:Procedure

To 3ml of cyclohexanol in a dry test tube, add 0.5ml of Conc.

:H2SO4and perform the following experiments

Test Observation Result

Bromination-1 The orange colour It is unsaturated

To 1ml of cyclohexene of bromine .compound
in a test tube add drops discharged
of bromine immediately

Potasium -2 The violet colour It is unsaturated

Permanganate Test of the .compound
In a test tube Put 1ml of Permanganate
cyclohexane+ few drops disappears
from dil KMnO4 acidify .immediately
.with sulfuric acid

11
 Acetylene
H-CC-H
: Preparation of Acetylene
Acetylene gas prepared by adding water to Calcium Carbide
CaC2
: Procedure
To 0.25gm of Calcium Carbide in a dry test tube add 1ml of water
and the acetylene gas will appear, perform the following
:experiments on it

Test Observation Result

Bromination-1 The orange colour It is unsaturated

Pass the acetylene gas of the bromine .compound
on a test tube contains disappear
.bromine immediately

Potasium - 2 The colour of the It is unsaturated

Permanganate Test Permanganate .compound
Pass the acetylene gas disappears
on a test tube contains .immediately
dil KMnO4 acidify by
.Conc. H2SO4
Pass the acetylene -3 White precipitate HCCAg
gas on a test tube that .forms silver acetylide
contains Ammonical
.silver nitrate

12
 Aromatic Hydrocarbons

Benzene

Test Observation Result

: Le Rosen test- 1 Red-brown colour

To 1 ml of benzene add .appears
1ml of formaldehyde,
and then add few drops
.of H2SO4
Nitration- 2
To 5ml of equal Yellow oily layer
volume of HNO3 and will be separated
Conc. H2SO4 add
gradually 1ml of Nitro benzene
Benzene with shaking,
cool the mixture for
about 2 minutes, pour
into cold water

13
 Toluene

CH3

Test Observation Result

Nitration-1
To one ml of HNO3 Yellow oily layer
in a test tube add will be separated
1ml of sulfuric acid
then add gradually
0.5ml of Toluene o-Nitro P-Nitro
with shaking then toluene toluene
pour the content of
the tube in beaker
.that contain ice

14
 Alcohols
Monohydric Alcohols

Methanol
CH3OH

Test Observation Result

Oxidation- 1 The orange colour Cr2(SO4 )3

5ml of K2Cr2O7 of the solution
solution + 2ml .changes to green
[CH3OH + dil.
H2SO4 ] warm in
.water bath
Esterification - 2 Oil of winter
1ml of CH3OH + .green forms
0.5gm salicylic acid
+Conc. H2SO4heat
in water bath for 5
Methyl salicylate
min.cool then pour
the content of the
test tube in a few ml
of cold water in a
.basin
: Iodoform test- 3 ve-
3ml of iodine
solution+1ml of
CH3OH + NaOH
Solution drop wise
until the iodine
colour just
disappear

.W.B

15
 Ethanol
CH3CH2OH

Test Observation Result

Oxidation- 1 The orange colour Cr2(SO4 )3

1ml of C2H5OH + of the solution
K2Cr2O7 +2drops of .changes to green
dil H2SO4 then heat
.in water bath

Esterification - 3 Fruity odor

1ml of C2H5OH appears CH3COOC2H5
+0.5 gm of Sodium Ethyl Acetate
acetate+ Conc.
H2SO4heat in water
bath for 5 min. then
pour the content of
the test tube in ice
.cold water
: Iodoform test - 3 .Yellow ppt CHI3
Iodoform

16
 Dihydric Alcohols

Ethylene glycol

Test Observation Result

Action of - 1 Pink colour

potassium
hydrogen sulphate:
Heat 1ml of ethylene
glycol with 3gm
potassium hydrogen
sulphate on direct
flame, then collect
the acetaldehyde
given in another test
tube. Test for
acetaldehyde by
Schiffs reagent

Borax test- 2 Pink colour

To 1% of borax appears with
solution in a test tube, heating and
add drops of phenol disappears with
phethalen (Ph.Ph.) then .cooling
add drops of ethylene
.glycol, heat

17
 Trihydric Alcohols
Glycerol

Test Observation Result

: Acrolein test - 1 Characteristic and CH2=CH.CHO

Heat 0.5ml of glycerol irritating odour Acrolien
with 1gm of finely .produced
powdered potassium
hydrogen sulphate 

Borax test- 2 Pink colour

To 1% of borax appears with
solution in a test tube, heating and
add drops of phenol disappears with
phethalen (Ph.Ph.) then .cooling
add drops of glycerol,

.W.B

18
 Aldehydes

Formaldehyde
O
H C H
Test Observation Result

: Reduction Reaction- 1 A brilliant silver Ag+HCOOH

a-1ml of HCHO mirror is deposited
few drops of + on the inner walls
, ammoniacal AgNO3 .of the test tube

..W.B
If the tube heated .Black ppt Ag2O
.directly
b- 1ml HCHO+2ml of Reddish brown Cu2O
Fhlings solution .ppt Cupric oxide
[fehling A +fehling B]

.W.B
Colour reaction of - 2 Pink colour
: formaldehyde
1ml HCHO+1ml of
Schiffs reagent

: Iodoform test - 3 ve-

19
 Acetaldehyde
O
H3 C C H

Test Observation Result

+CH3CHO(1ml)- 1 Silver Mirror Ag

Ammoniacal AgNO3 
.W.B
CH3CHO+ (1ml)- 2 Cu2O
.Red ppt
Fehlings reagent 
.W.B
: Schiffs reagent test - 2 .Red colour forms Acetaldehyde is
1ml CH3CHO +1ml of .an aldehyde
Schiffs reagent

Sodium - 4 .Red colour forms

:nitroprusside test
1ml of freshly prepared
solution of sodium
nitroprusside + CH3CHO
solution +dil. NaOH
.solution in excess
: Iodoform test - 5 Yellow crystals CHI3
Iodoform

20
 Chloral Hydrate

CCl3CHO.H2O

Test Observation Result

Action of sodium - 1 Oily drops forms CHCl3

: hydroxide with Chloroform
0.5gm of chloral hydrate+ characteristic
few drops NaOH  .odor

Solution of chloral - 2 Silver mirror Ag

hydrate +Ammonical
AgNO3 
.W.B

3-1ml of chloral hydrate+ .Red ppt Cu2O

1ml of Fehlings solution

.W.B
.

21
 Aliphatic Ketones

Acetone
CH3COCH3

Test Observation Result

drops of freshly (3) - 1

prepared solution of
10% sodium
nitroprusside +5 drops
of Acetone in 2ml H2O
+3 drops of dil.
.10%NaOH solution
Orange red
colour
: Iodoform test- 2 ve+ CHI3
: Oxidation - 3 Violet colour CH3COOH
2ml of acetone +dil of
H2SO4 + dil. KMnO4 permanganate
warm .is discharge

4-1ml of Acetone+(2ml) Yellow needles

of 2,4dinitrophenylhydrazine

Aceton2,4-
dinitrophenylhydrazone

22
 Carboxylic acids

Formic acid

HCOOH

Test Observation Result

: Acidity test- 1 Effervescence with CO2

1ml of HCOOH +solid evolution of gas
NaHCO3
: Ferric chloride test - 2 Red colour 3
Fe(HCOO)
Neutral solution of 
HCOOH +few drops of 
FeCl3 Fe(OH)2(HCOO)
.Brown ppt
Basic Ferric
formate
Ammonical silver - 3 Silver mirror
: nitrate test
Neutral solution of
HCOOH + Ammonical
AgNO3  Ag
4-1ml N.S of HCOOH+ .White ppt Hg2Cl2
1ml Hg2Cl2
If aqueous NH3 added
.ppt. turns black Hg
dil. HCOOH+ (1ml) - 5 Decolourization of
2ml of Na2CO3 solution .violet colour
+ 2 drops of KMnO4

23
 Acetic acid

CH3COOH

Test Observation Result

Acidity test- 1 Effervescence CO2

N.S+ FeCl3 - 2 Red ppt. boil 3

Fe(CH3COO)
.Brown ppt Ferric acetate

Fe(OH)(CH3COO)
2
Basic Ferric acetate
Ester formation - 3 Fruity odor CH3COOC2H5
C2H5OH + (2ml) of (2ml) Ethyl acetate
CH3COOH ]+1 ml H2SO4
.min. pour into NaHCO3 sol 5
.W.B

24
 Succinic acid

CH2COOH

CH2COOH

Test Observation Result

Acidity tes- 1 ve+

N.S+ FeCl3 - 2 Reddish brown

.gelatinous ppt

: Fluorescein test- 3 Red colour forms

resorcinol+ 1gm (1gm) .with intense green Formation of
Succininc acid+ 3drops .Fluorescenece
conc. H2SO4 , melt
pour over excess dil
NaOH

25
 Oxalic acid
COOH
 .2H2O
COOH

Test Observation Result

: Acidity test- 1 ve+

2ml N.S + few drops - 2 White ppt.on cold

of CaCl2
Calsium oxalate
3-1ml KMnO4 +1ml Decolouraization CO2 +MnSO4
Oxalic acid+ drops dil. of violet colour
H2SO4 warm

: silver nitrate test - 4 .White ppt

N.S. + AgNO3

26
 Tartaric acid
HO CH COOH
HO CH COOH

Test Observation Result

: Acidity test- 1 Effervescence CO2

N.S +CaCl2- 2 White ppt. after

scratching

Ammonical silver - 3 Silver mirror Ag

: nitrate test

N.S + AgNO3 - 4 .White ppt

: Fentons reagent- 5 Intinse violet

dil. Solution of tartaric colour forms
acid +1 drop of freshly
prepared FeSO4 + 2 drops
H2O2 +excess of NaOH
: Denigens test - 6 Violet colour of
Deniges A +5ml of (1ml) permanganate is
tartaric acid, boil, add 1- .discharged
2 drops Deniges B
Deniges B:KMnO4*
Deniges A: HgSO4*

27
 Citric acid
CH2 COOH
HO C COOH
CH2 COOH

Test Observation Result

: Acidity test- 1 Effervescence CO2

N.S +CaCl2- 2 White ppt. after

boiling

N.S + AgNO3 - 3 White ppt

: Fentons reagent- 5 ve-

: Denigens test - 6 Colour of

permanganate is
discharged. then a
heavy white ppt.
.forms

28
 Lactic acid

CH3CH(OH)COOH

Test Observation Result

: Acidity test- 1 Effervescence CO2

Alkaline potassium - 2
: permanganate test Decloronization
Dissolve lactic acid in .occurs
NaHCO3 solution +
KMnO4 drop by drop
warm

: Idoform test - 3 .ve+

29
 Aromatic acid

Benzoic acid
O
C OH

Test Observation Result

: Acidity test- 1 Effervescence CO2

Solid acid+ NaHCO3
Solution

N.S +FeCl3 - 2 .Buff ppt

: Soda lime test- 3 .Odor of Benzene

Benzoic acid + Soda
.lime  CO2 +
: silver nitrate test - 4 .ve+

30
: Esterification test - 5
Solid + C2H5OH +conc. Characteristic
H2SO4  odor
.W.B Ethyl benzoate
Pour over Na2CO3
solution

Salicylic acid
COOH
OH

Test Observation Result

Acidity test- 1 Effervescence CO2

N.S +FeCl3 - 2 Violet colour

: Phthalein test- 3 Bright red colour

Phthalic anhydride
+salicylic acid+ few
drops of conc. H2SO4+
Fission pour over
excess NaOH
: Soda lime test- 3 .Odor of phenol
Salicylic acid + Soda
lime 

N.S + AgNO3 - 4 White ppt

31
 Silver salicylate
: Esterification test - 5 Oil of winter
0.5g Salicylic acid + green
2ml C3HOH +3 drops
conc. H2SO4 
.W.B Methyl salicylate
Pour over Na2CO3
solution

Phthalic acid

Test Observation Result

Acidity test- 1 ve+

N.S +FeCl3 - 2 .Buff ppt

Soda lime test - 3 .Odor of benzene

: Phthalein test- 4 Bright red colour

Few crystal of phenol+
Phthalic acid or its
anhydride+ few drops
of conc. H2SO4 Fussion
cool, dissolve in water
add excess NaOH

32
 Cinnamic acid

Test Observation Result

Acidity test- 1 ve+

N.S +FeCl3 - 2 .Buff ppt

: Oxidation - 3 decolourisation
Dissolve (0.1)gm
cinnamic acid in 5ml of
10% Na2CO3
KMnO4 drop by 1% +
drop
: Bromine test- 4 Colourless oil (C6H5.CH=CHBr)
Dissolve (0.2)gm of
cinnamic acid in 5ml of Bromostyrene
Na2CO3 +bromine water
drop by drop

33
 Ammonium salt

RCOONH4

Test Observation Result

salt +NaOH - 1 odour of NH3

Ammonia
Sodium carbonate - 2 odour of NH3
: paste test Ammonia
Solid salt +solid
Na2CO3,moist with 1
drop of water, ground
on watch glass
, CaCl2 3- Aqueous solution + FeCl3 See the table

Acid (solution of FeCl3 CaCl2

salt)
Ammonium -1 Deep red ve-
acetate
Ammonium -2 Red ppt. of the ve-
formate ferric salt change to
brown on boiling

34
Ammonium -3 ve- White ppt. on cold
oxalate insoluble in acetic
acid
Ammonium -4 ve- White ppt. on
tartarate scratching soluble in
hot acetic acid
Ammonium citrate-5 ve- White ppt. after
boiling insoluble in
hot acetic acid
Ammonium -6 Redish brown
succinate .gelatinous ppt

Ammonium -7 .Buff ppt

benzoate

Ammonium -8 Buff ppt. that ve-

phthalate dissolve in HCl
Ammonium -9 and white ppt of White ppt. insoluble
cinnamate free acid formed in acetic acid
Ammonium -10 Violet colour ve-
salicylate

35
 Amides

Formamide

HCONH
2
Test Observation Result

: Hydrolysis - 1 Odor of Ammonia NH3+HCOOH

Boil formamide+15ml
of 10% solution of
NaOH

Acidify with dil H2SO4

+NH4OH, identify acid Red colour
by FeCl3

36
 Acetamide

CH3CONH2

Test Observation Result

: Hydrolysis - 1 ve+ NH3+Acetic acid

Identify the acid

37
 Urea

NH2CONH2

Test Observation Result

of urea ( 1gm)- 1 Ammonia odor

+15ml 10% solution of
NaOH

Formation of - 2 Violet colour H2N-CO-NH-CO-NH2
: Biuret test
urea melt (0.2gm)
dissolve in 2ml of cold
water +1drop very dil
CuSO4

38
 Imides
Succinimide

Test Observation Result

: Hydrolysis- 1 odour of
1gm succinimide Ammonia
+15mlof 10% aq.
NaOH boil. cool,
. acidify with H2SO4 Redish brown
gelatinous
N.S+ FeCl3
Florescein - 2 Green
: reaction florescent
Succinimide (0.1gm)
+(0.1gm) resorcinol
+2drops conc. H2SO4
Fussion add water Pour

39
into excess NaOH

Amines
Aniline

NH2

Test Observation Result

: Salt formation - 1 Mass C6H5NH2.HCl

crystalline
2ml aniline+5ml conc. obtained Aniline hydrochloride
HCl, cool in cold water
: Azo-dye test - 2 .Red –dye ppt
2ml aniline+1ml conc.
HCl +3ml water, cool in
ice + 3ml of NaNO2
solution with constant
shaking
To a cold solution of -

40
Naphthol+ excess 10%
NaOH
: Bromine water test - 3 .White ppt
Dissolve 5-6 drops of
aniline in water; add
bromine water until the Tribromo aniline
.colour is no longer fade

Aniline Salts

Aniline Hydrochloride

Test Observation Result

: Acidity test - 1 ve+

Solution of Aniline - 2 .White ppt
hydrochloride+AgNO3
: Azo-dye test- 3 ve+
Solution of Aniline - 4 ve-
hydrochloride+BaCl2

41
 Aniline Sulphate

Test Observation Result

: Acidity test - 1 ve+

Solution of Aniline - 2 ve-
hydrochloride+AgNO3
: Azo-dye test- 3 ve+
Solution of Aniline - 4 .White ppt BaSO4
hydrochloride+BaCl2

42
 Phenols

Organic FeCl3 Azo.dye test Phthalien Test

compound solution
Phenol Violet colour . Orange ppt Red colour
OH

Catechol Green colour ve- Blue colour

which darken

Resorcinol Violet colour . Orange ppt Green

OH fluorescence

OH

43
 Quinol Deep green ve- Purple colour
. ppt

Exess
FeCl3
. Yellow ppt

OH
Naphthol α- . Green pp Brownish Green colour
OH red
Exess
FeCl3

. Violet ppt

Naphthol β- Green colour . Orange ppt Faint green

OH fluorescence

Organic FeCl3 solution Azo.dye test Phethalien Test

compound
Pyrogallol Orange-red . Orange ppt ve-
colour

Phloglucinol Dark-violet . Orange ppt ve-

44
 Anilides
Acetanilide

Test Observation Result

: Hydrolysis- 1 Odour of
1gm of acetanilide acetic acid
+10mlof 70% H2SO4 CH3COOH+
Boil dil with 3ml of
20min

45
 Heterocyclic Bases
Hexamethylenetertamine
6N4(CH2)
( Hexamine)

Test Observation Result

: Hydrolysis- 1
soild +soda (0.5gm)
.Odor of crab
lime 

46
Action of nitrous - 2 Effervescence Trimethylene-
: acid and colourless trinitrosoamine
0.5gm +few ml of HCl crystals forms
+2ml of 20% NaNO2 in
.cold, cool in ice

Amino acids
Aliphatic amino carboxylic acids
Amino acetic acid
Glycine
NH2-CH2-COOH

Test Observation Result

Glycine+ ( gm 0.5 )- 1 Slow evolution of CO2

Na2CO3 Solution gas
: Sorensens reaction- 2
0.2gm glysine+ few drops
of water in tubeA+2drops
ph.ph.+ very dil. NaOH
drop by drop Pink colour
47
In tube B 2ml 10%
formaldehyde +drops
ph.ph+ very dil. NaOH Pink colour
Pour B into A Decolourisation of
pink colour
Methylene amino
dil NaOH can acetic acid
restore of pink
colour
3-1ml of glycine+FeCl3 Deep red colour

Aromatic amino-carboxylic acid

Anthranilic acid

Test Observation Result

Soild + Na2CO3 - 1 Effervescence CO2

solution
: Heating with sodalime- 2 Odour of aniline
Soild+soda lime 

: Diazotization- 3 ve+

48
 0.2g anthranilic+4ml dil
HCl, cool in ice +slowly
5ml of cold 20% NaNO2
divid intoCOOH
A,B
a-pour A to a cold
OH
alkaline
sol. -naphthol Brilliant red dye
obtained
b- boil B, cool and shake .White ppt Salicylic acid

Aromatic amino sulphonic acid

Sulphanilic acid

Test Observation Result

Soild + Na2CO3 - 1 Effervescence CO2

solution
: Azo-dye test- 2 ve+

solution +BaCl2 - 3 ve-

49
 Carbohydrate

: Molisch test
g of sugar +2ml of water+ 2-3 drops of alcoholic sol. of - 0.1
naphthol, carefully pour 1ml conc. H2SO4 on the side of the test
tube deep violet ring
: Rapid Furfural test
1ml dil sol. of sugar +1ml alcoholic sol. Of -napthol +6-8 ml of
.conc. HCl ,boil violet colour
.3min
: Barfoid test
1ml of conc. Soln. of sugar +3ml of Barfoid reagent,  red
ppt. W.B
.
:. Action of 10% NaOH sol
0.2g of sugar+ 5ml of 10% NaOH boil Yellow colour then
brown then caramel colour

50
 : Iodine test
Sugar soln.+1-2 drop of dil. Iodine sol. Deep blue colour
.disappears on heating

Molisch Fehiling Barfoid Iodine Furfural Heating

test test test test test NaOH+
Glucose ve+ ve+ ve+ delayed
C6H12O6 violet
Fructose ve+ ve+ ve+ Immediate
Fruit sugar violet
Lactose ve+ ve+ ve- ve+
C12H22O11
Maltose ve+ ve+ ve- ve+
C12H22O11
Sucrose ve+ ve- ve-
C12H22O11
Starch ve+ ve- ve+
n( C6H10O5)

Scheme for identification of organic compounds

Liquids
I )-liquid +Schiffs reagent

Violet colour immediately appears -ve go to II

It is formaldehyde or acetaldehyde
To differentiate, do Resorcinol test or Sodium nitroprossid test

Resorcenol test Sodium nitroprossid test

1ml of unknown +1drop of resorcinol 1ml of unknown +0.5 ml of

Solution + 1ml of conc. H2SO4 on the Sodium nitrobrossid solution
Wall of the test tube. Then add NaOH drop by drop

51
 Red violet ring with -ve the solution turns into -ve
white ppt. It is acetaldehyde deep red blood colour it is
Change to red ppt. formaldehyde
It is formaldehyde

II) Liquid +Sodium bicarbonate solution (NaHCO3)

Effervescence -ve
It is carboxylic acid Go to III
( formic acid, acetic acid or lactic acid)
To differentiate, do FeCl3 test
: FeCl3 test
N.S+ FeCl3 solution

Red colour heat brown ppt. –ve

It is formic acid or acetic acid It is lactic acid
To differentiate do KMnO4 test
2ml of acid +2 drops of KMnO4solution

The colour of the permanganate -ve

Disappears it is acetic acid
It is formic acid

III) 1ml of liquid +5ml of iodine, shake then add NaOH drop by drop

. Yellow ppt
It is acetone

52
 Solids
+ I)Molish s test: Dissolve the solid in H2O
-Naphthol(1ml)+conc.H2SO4(0.5ml) dropwise on the wall of the
test tube

Violet ring -ve

It is Carbohydrate Go to II
May be Glucose, Fructose, Lactose, Maltose
.Sucrose or Starch
: a)Fehlings test
Fehling A(1ml)+Fehling B(1ml)+solution(1ml)

Red ppt. Reducing sugar -ve

53
 May be Glucose, Fructose, Lactose or Maltose Succrose or starch
b)Barafoids test: Go to (c)
Solution(1ml)+Barafoids reagent

Red ppt. It isMonosaccharide -ve it isDisaccharides

May be Glucose or Fructose.
d) Rapid Furfural test:
Solution (1ml)+-Naphthol (1ml)+
boil
May be Lactose or Maltose
e) Heating with NaOH(30%)
Solution(1ml)+30%NaOH (3ml)
conc. HCl(5ml)
boil

Immediate violet delayed violet slight Browne colour

Colour colour It is Lactose or Maltose
Ketose Aldose
( Glucose) ( Fructose)

C) Iodine test: Solution (1ml)+Iodine sol. (3drops)

Blue colour it is Starch -ve It is Sucrose

II) solid+ NaOH solution (30%)

Odor of ammonia -ve

It is ammonium salt of an acid Go to III
a) Unknown solution +FeCl3 solution
If (a)is +ve

.Red colour heat brown ppt. Buff ppt. Violet ppt

it isAmmonium formate it is It is
or Ammonium acetate Ammonium Ammonium
benzoate salicylate

54
 -:To differentiate do KMnO4 test
+ 2ml of unknown solution
2drops of KMnO4 solution

The colour of the -ve

Permanganate it is Ammonium
It is Ammonium acetate
formate

-:If (a)is –ve do

b) 2ml of unknown +CaCl2

White ppt. on cooling White ppt. after scratching White ppt. after boiling
It is It is It is
Ammonium oxalate Ammonium tartarate Ammonium
citrate

III) Unknown + sodium bicarbonate solution (NaHCO3)

Effervescence -ve
It is free acid o aniline salt Go to IV
:A)To identify the unknown do azo dye test

1 3 2

1m of unknown NaNO2 solution -naphthol+ excess NaOH

3ml of conc. HCl+
put the tube in ice bath*
Add the tube2 to 1 drop by drop and then add the mixture to tube 3*

If azo dye test is +ve(Red ,orange color or ppt.) It is aniline salt

55
:To identify the aniline salt
Unknown solution +BaCl2 solution

White ppt. –ve

It is aniline sulphate It is aniline hydrochloride

If azo dye test is -ve

B) i) N.S +FeCl3 solution

If (i)is +ve

Buff ppt. Violet colour

It is benzoic acid It is salysilic acid

If (i)is -ve

ii) N.S+CaCl2 solution

White ppt. on cooling White ppt. after scratching white ppt. after boiling
It is oxalic acid It is tartaric acid It is citric acid

IV) Unknown soluble in ethanol +FeCl3

Green colour Green colour turn into violet violet colour

, It is -naphthol it is -naphthol It is Phenol

56
Resorsinol or m- cresol
To differentiate do
Phthalein test:0.5g of
phthalien anhydride +(2-3) drops of
Conc H2SO4 heat and then add the
mixture to the beaker of NaOH solution

Violet-blue Greenish red purple

colour colour colour
It is m-cresol it is Resorsenol it is phenol

: References

Practical Organic Chemistry, Chemistry department -1

Faculty of Science Alexandria University
A-Text Book of Practical Organic Chemistry including -2
.qualitative organic analysis, third edition by vogel
Hetero cyclic compounds chemistry by Morrsen and -3
Boyd

57