Yemen Republic
Taiz University
Faculty of Applied Science
Dep- of Chemistry
A laboratory manual on
(1)
Prepared By:
T- Muataz Sufyan
October / 2013
Taiz University
Org. Chem. Lab.
Contents
NO
Page No
1
Lab Safety
2
2
Chemical Hazard Symbols
3
3
First Aid in Lab
4
4
Lab Equipment
5
5
An Introduction to Organic Chemistry
7
6
Identification of Alcohol
10
7
Identification of liquid Carboxylic acids (Aliphatic)
19
8
Identification of Solid Carboxylic acids (Aliphatic)
25
9
Identification of Solid Carboxylic acids (Aromatic)
31
10 Identification of Solid Carboxylic acids salts
37
11 Identification of carbohydrates
41
12 The Periodic Table of Elements
46
1
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
1. Never work alone in the lab.
2. In the lab area do not touch any equipment, chemicals, or other
materials .
3. Do not drink or eat food and gum in the lab.
4. Always work in a well-ventilated area.
5. Read carefully instructions of equipment before use .
6. Keep hands from face, eyes, mouth, and body while using chemicals
or lab equipment and wash your hands with soap and water after
performing all experiments.
7. Contact lenses may be not being worn in the lab.
8. Long hair must be tied back, and clothing must be secured and shoes
must completely cover the foot.
9. A lab coat,gloves should be worn during lab experiments.
10. If a chemical should splash in your eyes or on your skin,
quickly wash with water for at least 20 minutes.
11. All chemicals in the lab are dangerous because of that do
not taste, or smell any chemicals.
12. Never return unused chemicals to their original container.
13. Never remove chemicals or other materials from the lab area.
14. Examine glassware before each use and never use cracked or dirty
glassware.
15. Do not inter hot glassware in cold water.
16. Do not operate a hot plate by yourself and take care that hair,
clothing, and hands are a safe distance from the hot plate at all times.
17. Never look into a container that is being heated.
2
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Chemical Hazard Symbols
Toxic substances
Flammable substances
Explosive substances
harmful substances
oxidizing substances
Corrosive substances
3
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
First Aid in Lab
Chemical or causes
Neutralizing wash or treatment
Acids
2M ammonium carbonate
Alkalis
M acetic acid
Bromine
2M ammonia
Hydro fluoric acid
As for acids , then hospital treatment.
Phenol
Ethanol , then hospital treatment.
Phosphorus
0.1 M copper sulphate.
Sodium
Ethanol on a cotton wool pad.
Poison swallowed
Plenty of water at once if the patient is conscious.
Corrosive poisons
Plenty calcium hydroxide(lime water) as soon as.
Gassing
In case of gassing acknowledge of artificial respiration.
Cuts
The wound is washed well with cold water,
inspected,
And any foreign bodies removed. Then an
intersected
cream of certrimide is applied and the affected part
protected with a suitable dressing.
Severe bleeding
Firm pressure round the wound, a cover with a pad
And firm bandaging.
Electrical mishaps
These are usually avoidable by the correct
installation of equipment.
4
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Lab Equipment
Test Tube Brushes
Pipet
Beaker Tongs
Test Tube Holder
Test Tube Racks
Dropper
Test Tube
Wash Bottle
Spatulas
5
T- Muataz Sufyan
Taiz University
Glass Stir Rod
Org. Chem. Lab.
Reagent Bottles
Conical flask
Watch Glass
Cylinder
Water Bath
Bunsen Burner
Beaker
Hood
6
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
An Introduction to Organic Chemistry
Organic chemistry is the study of carbon containing compounds and their
properties. This includes the great majority of chemical compounds on the
planet, but some substances such as carbonates and oxides of carbon are
considered to be inorganic substances even though they contain carbon.
Organic chemicals are continually released into the environment in large
quantities. For example, global production of mineral oil exceeds 3 billion
tonnes a year and the amount of new organic chemicals made each year in
research laboratories and industry is increasing exponentially. There is a need
to understand how these organic molecules will interact with the environment
in order to minimise their impact. To achieve this the type of reactions that
organic molecules undergo needs to be understood.
How do you tell the difference between an Organic and an Inorganic
Compound?
Probably the best way is to compare the chemical and physical properties of
substances to the table below. If they concur with those properties on the left
column of the table then the substance is probably organic, whilst if they
compare to the properties listed in the right column then the substance is most
likely inorganic.
Inorganic Compounds
Organic Compounds
Mostly ionic bonding.
Use mostly covalent bonding.
Are generally solids with high melting
points.
Are gases, liquids or solids with low
melting points.
Many are water soluble.
Mostly insoluble in water.
Most are not soluble in organic solvents.
Many are soluble in organic solvents such
as petroleum, benzene and hexane.
When dissolved in water conducts
electrical current.
Solution in water generally do not conduct
electricity.
Most not combustible.
Almost all burn.
Often undergo fast chemical reactions
Slow to react with other chemicals.
Table 1: Comparison of the properties of organic and inorganic compounds
7
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
* Organic Molecules
All organic molecules contain carbon (C), virtually all of them contain
hydrogen (H), and most contain oxygen (O) and/or nitrogen (N) atoms. Many
organic molecules also have halogen atoms such as fluorine (F), chlorine (Cl),
bromine (Br), or iodine (I). Other atoms in organic compounds include sulfur
(S), phosphorous (P), and even boron (B), aluminum (Al), and magnesium (Mg)
* Why does carbon form so many compounds?
Carbon has the ability to bond with itself to form long chains and ring
structures; hence it can form molecules that contain from one to an infinite
number of C atoms.
Functional Groups
Type of Functional Group
General Formula
Alkane
C
Alkene
C
C
Alkyne
C
C
Alkanol (old name alcohol)
C
OH
Amine ( Primary)
C
NH2
C
Amine ( Secondary)
C
NH R
Amine (Tertiary)
C
N
R
R
O
Alkanal (old name aldehyde)
C
C
H
O
Alkanone ( old name k etone)
C
C
C
O
Ester
C
C
O
R
O
Alkanoic acid (also called carboxylic acid)
C
OH
O
Amide
R
C
N
8
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
ALCOHOLS COMPOUNDS
R-OH
Alcohols are compounds contains one or more hydroxyl groups (OH)
Classification of Alcohols
Alcohols are classified according to the nature of the carbon to which
the -OH group is attached. This classification is very useful in
categorizing the reactions of alcohols. Primary alcohols (designated 1o)
have the -OH group attached to a carbon atom bonded to only one
nonhydrogen group. In secondary alcohols (2o), the -OH group is attached
to a carbon atom bonded to two nonhydrogen groups. In tertiary alcohols
(3o), the -OH group is attached to a carbon atom bonded to three
nonhydrogen groups.
ALCOHOLS
Primary
R
CH2
OH
Secondary
R
CH
Tertiary
R
R
R
OH
C
R
OH
CH3
CH2
CH2
OH
CH3
CH
OH
CH3
CH3
CH3
C
CH3
OH
9
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Identification of Alcohol
Oxidation test:
It was found that Primary alcohols oxidizing to aldehyde the Secondary
alcohols oxidizing to ketone, but tertiary alcohols not oxidized according to the
following equations.
O
RCH2OH
O
[O]
R
Primary alcohol
C
H
[O]
R
C OH
carboxylic acid
aldehyde
O
R2CHOH
[O]
Secondary alcohol
R3COH
R
C
R
[O]
No reaction
Ketone
[O]
No reaction
Tertiary alcohol
oxidation loss of H2
gain of O, O2
10
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
1-Methanol CH3OH
Methyl alcohol is colorless liquid , have characteristic odor , miscible in water ,
toxic , burned by blue flame .
Test
Observation
1-Oxidation Reaction:
In a test tube put 1 ml of methanol
The orange color
+1ml of potassium dichromate
K2Cr2O7 + drops of conc.sulphuric
of the solution
changes to green.
acid .
Result
The green color is chromium
sulphate Cr2(SO4 )3 which
formed due to the oxidation
of methanol to Formaldehyde
O
K2Cr2O7 + 4 H2SO4 + 3 CH3OH
3H
H + K2SO4 + Cr2(SO4)3 + 7 H2O
C
Formaldehyde
2-Esterification :
In a test tube put 1ml of methanol
+ 0.5 gm of salicylic acid + drops
of conc. H2SO4 & heat in water
Vix (oil of winter
green ) odor
bath for 3 min. then cool and pour
The product is
methyl salicylate.
appear.
the content of the test tube into
beaker contains Na2CO3 .
COOH
OH
+
CH3OH
H2SO4
COOCH3
Conc
OH
+ H2O
Methyl Salicylate
11
T- Muataz Sufyan
Taiz University
2-Ethanol
Org. Chem. Lab.
CH3CH2OH
Ethyl alcohol is colorless liquid , have characteristic odor , miscible in water ,
toxic , burned by colorless flame .
Test
1-Oxidation Reaction:
In a test tube put 1ml of ethanol
+1ml of potassium dichromate
K2Cr2O7 + drops of conc.
sulphuric acid .
Observation
Result
The orange color
of the solution
changes to green.
The green color is chromium
sulphate Cr2(SO4 )3 which
formed due to the oxidation of
ethanol to acetaldehyde.
O
K2Cr2O7 + 4 H2SO4 + 3 CH3CH2OH
3 CH3
C
H + K2SO4 + Cr2(SO4)3 + 7 H2O
acetaldehyde
2-Esterification :
In a test tube put 1ml of ethanol
+ 0.5 gm of sodium acetate
+ drops of conc. H2SO4 & heat in
water bath for 3 min. then cool and
pour the content of the test tube into
beaker contains Na2CO3 solution .
H2SO4
CH3COONa + CH3CH2OH
Conc
Fruity odor
appears
(apple odor) .
The product is
Ethyl acetate.
CH3COOCH2CH3 + NaOH
Ethyl acetate
3-Iodoforms Test :
In a test tube put 1ml of ethanol
+ 3ml of iodine solution & heat in
water bath for 3 min. then cool &
add NaOH drop wise till the color is
straw yellow a pale yellowish ppt. of
iodoform is produced.
O
CH3CH2OH
[O]
CH3
C
The yellow ppt. is
Iodoform
CHI3 .
Yellow ppt.
formed.
O
H
NaOH
3 I2
CI3
-3 HI
C
Iodal
H
CH3I  + HCOONa
Iodoform
12
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
3-Glycerol
CH2
OH
CH
OH
CH2
OH
Glycerol is a colorless viscous liquid, melted at 10 °C, miscible in water and
alcohol and has a sweet taste.
The most characteristic test for glycerol is the Borax test.
Test
Observation
Result
The disappearance of (ph.ph)
1-Borax Test :
In a test tube add 2 drops of
The color
phenolphthalein (ph.ph) to
disappears and is
dilute borax solution then a pink
color on cold due to the
formation of strong acid and
by heating this acid
restored on
color is produced Add few
dissociated into boric acid
heating.
& glycerol , the pink color
drops of glycerol & shake.
3 NaOH + 4 H3BO3
Na2B4O7 + 7 H2O
CH2
OH
CH
OH +
CH2
OH
returned.
HO
CH2
O
CH
O
CH2
OH
B
Cold
Glyserol
B
OH
Hot
HO
O
+
H
+ H2O
Strong acid
Boric acid
{ Basic Media } Pink colour
_
{ Acidic Media } colourless
13
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
14
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
15
T- Muataz Sufyan
4- Borax test
3- Iodoforms test
2- Esterification
1- Oxidation
Test
Compound
Glycerol
Ethanol
Comparison
Methanol
Taiz University
Org. Chem. Lab.
16
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
CARBOXYLIC ACIDS
Carboxylic acids
Aromatic acid
Aliphatic acids
Formic
acid
Solid
Solid
Iiquid
Benzoic
acid
Acetic
acid
Oxalic
acid
Salicylic
acid
Phthalic
acid
Citric
acid
Tartaric
acid
carboxylic acids are organic compounds that have a carboxyl group
attached to an alkyl group(RCOOH) or to an aryl group (ArCOOH). The
'R' may be a hydrogen and the result is formic acid. They may be mono
carboxylated, multi carboxylated, substituted (e. g., hydroxyl groups), or
they may be aromatic.
Acids divided into two major classes.Aliphatic acid and aromatic acid.
17
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Identification of Carboxylic acids
1) Identification of liquid Carboxylic acids (Aliphatic)
2) Identification of Solid Carboxylic acids (Aliphatic)
3) Identification of Solid Carboxylic acids (Aromatic)
Neutral Solution of acid:
N.S of acid is the ammonium salt for acid
RCOOH + NH4OH
RCOONH4
+
H2O
Some chemical reactions used to identify such acids carried out on its N.S.
To Make Neutral Solution N.S :
Add to the acid aqueous NH3 (NH4OH) till the solution is just alkaline to
litmus. Boil the solution until the evolution of NH3 gas ceases ( this can
be ensured by exposing a red litmus paper to vapor ).
General properties for acids :
1. Acids react with alcohol in present of conc. H2SO4 produce ester with
specific odor.
'
RCOOH + ROH
H2SO4
'
RCOOR
+
H2O
2. N.S of acid with ferric chloride solution.Gives specific color for each
acid.
3. Acids Solution turns litmus paper to red.
♦ Aliphatic acids :
HCOOH
CH3COOH
COOH
HO
CH
COOH
COOH
HO
CH
COOH
CH2
HO C
COOH
COOH
CH2
Formic acid
Acetic acid
Oxalic acid
Taritaric acid
COOH
Citric acid
♦ Aromatic acid :
COOH
COOH
COOH
OH
COOH
Benzoic acid
Phthalic acid
Salicylic acid
18
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
1)Identification of liquid Carboxylic acids (Aliphatic)
1- Formic acids
HCOOH
Formic acid is a colorless liquid, immiscible in water, alcohol and
ether. It has a pungent irritating odor. All formate as soluble except those
of Ag, Hg, and some basic salt.
Test
1-Acidity test:
1ml of acid + 2ml of NaHCO3
Observation
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
CH3COONa + H2O + CO2 
CH3COOH + NaHCO3
Sodium formate
2-Ferric chloride test:
1ml of N.S. of acid + few drops
of FeCl3 .
Red color is ferric
Red color turned with format (HCOO)3Fe and
brown ppt. is basic
heating into Brown ppt.
ferric formate
(HCOO)Fe(OH)2
(HCOO)3Fe + 3 NH4Cl
3 HCOONH4 + FeCl3
ferric formate
(Red Color)

2 H2O
(HCOO)Fe(OH)2 
basic ferric formate
(Brown ppt.)
3-Mercury chloride test:
1ml of N.S. of acids + 1ml HgCl2 &
added excess then boil.
2 HCOONH4 + HgCl2
White ppt. immediately
appear &change to
gray ppt. with boiling .
White ppt. is Hg2Cl2
& the gray ppt. is
metallic Hg
Hg  + CO  + CO2  + 2 NH4Cl
19
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Test
Observation
4-Permanganate test:
1ml of warm acids + drops of
The color of KMnO4
Oxidation for formic
will disappear .
KMnO4 .
HCOOH
Result
[O]
acid below.
CO2  + H2O
5-Esterification test:
In dry test tube but 1ml of acids
+ 1ml of ethanol + 1ml of conc.
H2SO4 & then heat in water
Pleasant odor is
detected.
The odor due to the
formation Ethyl formate
HCOOC2H5
bath for 3 min., then pour into
beaker contain Na2CO3 solution .
HCOOH + CH3CH2OH
H2SO4
HCOOCH2CH3 + H2O
Ethyl formate
20
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
2- Acetic acid CH3COOH
Acetic acid is a colorless liquid, with a penetrating odor of vinegar ,
miscible with H2O, alcohol and ether . Most of its salts soluble with water
except those of Ag, mercurous and basic salts.
Test
1-Acidity test:
1ml of acid + 2ml of NaHCO3 .
Observation
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
CH3COONa + H2O + CO2 
CH3COOH + NaHCO3
Sodium Acetate
2-Ferric chloride test:
1ml of N.S. of acid + few drops
of FeCl3 .
Red color is Ferric
acetate (CH3COO)3Fe
Red color turned with
heating into Brown ppt. and brown ppt. is basic
ferric acetate
(CH3COO)Fe(OH)2
(CH3COO)3Fe + 3 NH4Cl
3 CH3COONH4 + FeCl3
ferric Acetate
(Red Color)

2 H2O
(CH3COO)Fe(OH)2 
basic ferric formate
(Brown ppt.)
3-Mercury chloride test
1ml of N.S. of acids + 1ml of
HgCl2 & added excess then
boil .
White ppt. Change to
yellow ppt. with
boiling.
Confirmatory test for
acetic acid.
21
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Test
Observation
Result
4-Permanganate test:1ml of warm acid + drops of KMnO4
The color will not
disappear .
No oxidation for acetic
acid occur.
apple odor.
This odor characteristic
for Ethyl acetate
CH3COOC2H5 .
5-Esterification test:
In dry test tube put 1ml of acids
+ 1ml of ethanol
+ 1ml of conc. H2SO4 &heat in water
bath then pour into beaker contain
Na2CO3 solution .
CH3COOH + CH3CH2OH
H2SO4
CH3COOCH2CH3 + H2O
Ethyl Acetate
Experiment to differentiate between Formic and Acetic acid
Test
Formic acid
1-Permanganate test:
1ml of warm acid + drops
The color disappear.
of KMnO4 .
2-Mercury chloride test:
1ml of N.S. of acid +1ml
of HgCl2 & added excess
then boil.
Acetic acid
The color will not
disappear.
White ppt. immediately
White ppt. change to
appear & change to
yellow ppt. with
gray ppt. with boiling.
boiling.
22
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
23
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
24
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
2)Identification of Solid Carboxylic acids (Aliphatic)
1-Oxalic acid
COOH
COOH
Oxalic acid is a colorless crystalline solid freely soluble in water and
alcohol, it undergo pyrolysis without charring up on heating.
Test
1-Acidity test :
0.25gm of acid +1ml of NaHCO3
solution .
COOH
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
COONa
+
COOH
Observation
Na2CO3
COONa
+ CO2  + H2O
Sodium Oxalate
2-Ferric chloride test :
1ml of N.S. + drops of FeCl3 .
No change for FeCl3
yellow color.
Oxalic or tartaric or
citric acid.
3-Calcium chloride test :
1ml of N.S. of acid +1ml of CaCl2 .
White ppt. on cold.
The ppt. is calcium
oxalate.
specific test for oxalic
acid.
COONH4
COONH4
+ CaCl2
COO
Ca 
COO
+ 2 NH4Cl
Calcium Oxalate
(White ppt.)
4-Denig's test :
2ml of N.S. + 2ml of denig's A
denig's A ( HgSO4 )
COONH4
COONH4
+ HgSO4
White ppt.
The ppt. is mercuric
oxalate
specific test for oxalic
acid.
COO
Hg  +
COO
Mercuric Oxalate
(NH4)2SO4
(White ppt.)
25
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
2-Tartaric acid
HO
CH
COOH
HO
CH
COOH
Colorless crystalline solid, freely soluble in water and alcohols. Heating of
acid or its salts, they undergo charring with evolution of burned sugar odor
Test
1-Acidity test :
0.25gm of acid +1ml of NaHCO3
solution .
HO
CH
COOH
Observation
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
HO
CH
COONa
+ Na2CO3
HO
CH
COOH
HO
CH
COONa
Sodium Taritarate
2-Ferric chloride test :
1ml of N.S. + drops of FeCl3 .
3-Calcium chloride test :
1ml of N.S. of acid +1ml of CaCl2 .
HO
CH
COOH
No change for FeCl3
yellow color.
oxalic or tartaric or
citric acid.
White ppt. appear after
scratching the inner wall
of the tube.
The ppt. is calcium
tartarate
specific test
for tartaric acid.
HO
CH
COO
HO
CH
COO
+ CaCl2
HO
CH
+ CO2  + H2O
COOH
Ca  + 2 NH4Cl
Calcium Taritarate
White ppt.
4-Denig's test :
2ml of N.S. + 2ml of denig's A
& heating until boiling then add
2 drops of deng's B .
Color of
permanganate will
disappear.
specific test for
tartaric acid.
26
T- Muataz Sufyan
Taiz University
3- Citric acid
Org. Chem. Lab.
HO
CH2
COOH
C
COOH
CH2
COOH
Citric acid is Colorless crystalline solid, freely soluble in water and alcohols.
By heating a heavy vapor with irritating smell evolved and finally undergo
charring.
Test
1-Acidity test :
0.25gm of acid +1ml of NaHCO3
solution .
HO
CH2
COOH
C
COOH + Na2CO3
CH2
COOH
Observation
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
HO
CH2
COONa
C
COONa + CO2  + H2O
CH2
COONa
Sodium Citrate
2-Ferric chloride test :
1ml of N.S. + drops of FeCl3 .
No change for FeCl3
yellow color.
oxalic or tartaric or
citric acid.
White ppt. appear
after boiling.
The ppt. is calcium
citrate
specific test of citric
acid.
3-Calcium chloride test :
1ml of N.S. of acid +1ml of CaCl2 .
HO
CH2
COONH4
C
COONH4 + CaCl2
CH2
COONH4
4-Denig's test :
2ml of N.S. + 2ml of denig's A
& heating until boiling then add
2 drops of deng's B .

HO
CH2
COO
C
COONH4
Ca
 + 2 NH4Cl
CH2
COO
Calcium Citrate
White ppt.
Color of
permanganate will
disappear and heavy
white ppt. formed after
add deng's B.
specific test of citric
acid.
27
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
28
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
29
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
30
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
3) Identification of Solid Carboxylic acids (Aromatic)
COOH
1- Benzoic acid
Benzoic acid is a white crystalline solid
undergo sublimation by heating partially soluble in cold water, freely
soluble in hot water and ethanol m.p. is 121 °C .
Test
1-Acidity test :
0.25gm of acid +1ml of NaHCO3
solution .
Observation
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
COOH
COONa
+ Na2CO3
2
+ CO2  + H2O
2
Sodium Benzoate
2-Ferric chloride test :
1ml of N.S. + drops of FeCl3 .
The ppt. is basic ferric
benzoate.
buff ppt.
COONH4
(COO)Fe(OH)2
+ FeCl3

+ NH4Cl
basic ferric benzoate
3-Estrification test :
0.25gm of acid +1ml of ethanol
+1ml of conc. H2SO4 &heat in water
bath 3 min. then pour into beaker
contain NaHCO3 solution .
Specific odor.
COOH
The odor due to Ethyl
benzoate.
COOC2H5
+ C2H5OH
H2SO4
+ H2O
Conc
Ethyl benzoate
31
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
COOH
2- Phthalic acid
COOH
Phthalic acid is a white crystalline
solid undergo sublimation by heating, partially soluble in cold water, freely
soluble in hot water and ethanol m.p. is 210 °C .
Test
1-Acidity test :
0.25gm of acid +1ml of NaHCO3
solution .
Observation
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
COONa
COOH
+ CO2  + H2O
+ Na2CO3
COONa
COOH
Sodium Phthalate
2-Ferric chloride test :
1ml of N.S. + drops of FeCl3 .
The ppt. is basic ferric
benzoate.
buff ppt.
COONH4
-
COO
+ FeCl3
Fe2  + NH4Cl
COONH4
3- Fluorescence test :
In a dry test tube mix equal quantities
of Phthalic acid and resorcinol with 2
drops of concentrated sulphuric acid.
Heat the mixture on direct flame for
1 minute until the mixture melts.
Cool and add excess of 10% sodium
hydroxide solution to get a
-
COO
ferric phthalate
red colour with green
fluorescence.
3
Special test for
Phthalic acid
(Fluorescence test)
32
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
COOH
3- Salicylic acid
OH
Salicylic acid is a white crystalline
solid undergo sublimation by heating, partially soluble in cold water, freely
soluble in hot water and ethanol m.p. is 159 °C .
Test
1-Acidity test :
0.25gm of acid +1ml of NaHCO3
solution .
Observation
Result
CO2 evolves with
effervescence.
The compound is
carboxylic acid.
COONa
COOH
2
+ Na2CO3
+ CO2  + H2O
2
OH
OH
Sodium Salicylate
2-Ferric chloride test :
1ml of N.S. + drops of FeCl3 .
COOH
3
Specific test of
salicylic acid.
Violet color.
COOH
+ FeCl3
+ NH4Cl
Fe
OH
-
O
ferric Salicylate
Violet color
3-Estrification test :
0.25gm of acid +1ml of methanol
+1ml of conc. H2SO4 &heat in water
bath 3 min. then pour into
beaker contain Na2CO3 solution
3
The odor due to
Methyl
salicylate ester.
Vix odor.
COOH
COOCH3
+ CH3OH
H2SO4
+ H2O
Conc
OH
OH
Methyl Salicylate
Vix Odor
33
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
34
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
35
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
36
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Identification of Carboxylic Acids Salts
Carboxylic acids salts are organic compounds with the general formula
(R/ArCOOM) where (R/ArCOO-) refers to the carboxylic acid part and (M+)
is the alkali part which, in this experiment, may be either a metal cation (Na+
or K+) or ammonium (NH4+). These salts are colourless or white crystalline
solids and are soluble in cold or hot water.
1- Identification of the alkali part (cationic part)
• Identification of sodium or potassium cations
Place about 0.1 g of the salt on the edge of a metal spatula and start
heating it gently on a flame with gradual increase in the heat strength.
Sodium and potassium salts leave a residual amount of solid on the spatula in
addition to the carbon coming from decomposition of the organic part. This
residual solid may be sodium carbonate or potassium carbonate and can be
detected, after cooling, by the addition of few drops of dilute hydrochloric
acid solution which results in a strong effervescence within the residual so lid
due to liberation of carbon dioxide gas.
During ignition observe the colour of the flame. Sodium salts burn with a
golden yellow flame whereas potassium salts burn with a purple flame.
• Identification of ammonium cation
Repeat the ignition procedure mentioned above and note that ammonium
salts don't leave any residual solid except the carbon coming from
decomposition of the organic part. After cooling, addition of few drops of
dilute hydrochloric acid does not result in any effervescence. Ammonium
cation can be detected as follows. Place few crystals of the salt in a test tube
and add 0.5 mL of 10% sodium hydroxide solution. At this stage free
ammonia is liberated and can be smelt easily:
R COONH4
+
NaOH
NH3  + R COONa
+ H2O
Ar COONH4
+
NaOH
NH3  + Ar COONa
+ H2O
2- Identification of the carboxylic acid part (anionic part)
The carboxylic acid part can be identified by the usual steps for
identification of carboxylic acids starting with ferric chloride test and,
37
T- Muataz Sufyan
Salicylate
Benzoate
or
Phthalate
red colour
with green
fluorescence
Phthalate
No
change
Benzoate
Fluorescence
test
Or
Citrate
Violet Color
Buff ppt
38
T- Muataz Sufyan
Acetate
The color
of KMnO4
will not
disappear
Formate
The color
of KMnO4
will
disappear
Permanganate
test
Formate or Acetate
Red Color
Citrat
e
Color of
KMnO4
will
disappear
&
white ppt
Yellow Color
Taritrate
Color of
KMnO4
will
disappear
denig's A
( HgSO4 )
+
deng's B
(KMnO4)
Oxalate or Taritrat
or Citrate
denig's A
( HgSO4 )
+
deng's B
(KMnO4)
2ml of Solution salt + drops of FeCl3
Oxalat
e
White ppt
denig's A
( HgSO4 )
Taiz University
Org. Chem. Lab.
according to the result observed; the proper special test should be performed
then to conclude the carboxylate name (formate, lactate, salicylate, etc.).
Can you skip the neutralization step in the reaction between
carboxylic acid salts and ferric chloride solution? Explain.
deng's B
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
39
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
40
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Identification of carbohydrate
* Carbohydrates :
Are organic molecules with the general formula Cn(H2O)n in 1:2:1 ratio. Although
carbohydrates constitute only 1 to 2 percent of cell mass, they provide the raw fuel for
cellular energy production. Carbohydrates are classified according to molecular size and
solubility. In general, the smaller molecules are more soluble than the larger ones.
Carbohydrates divide to :
monosaccharide
formula C6H12O6
e.g.
- glucose (grape sugar)
- fructose (fruit sugar)
aligosaccharide
polysaccharide
formula C12H22O12
e.g.
formula (C6H10O5)n
e.g.
- lactose (milk sugar)
- maltose (malt sugar)
- starch
- sucrose
- glaicogen
41
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
* To determine and compare between carbohydrate should follow these steps order :
solubility in water
dissolve
insoluble
mono or aligo
saccharide
polysaccharide
fehling test
iodine test
so it's starch
to confirm
+ve
so it's reducing sugar
blue color
lactose - maltose - glucose fructose
_ve
so it' s unreducing
sugar
barafoide test
it's sucrose
(test time)
red brown precipitate
after
red precipitate after
2 min
10 min
so it's
monosaccharide
so it's aligo saccharide
lactose - maltose
glucose - fructose
ozazone test
forfural test
in microscope
lactose
glucose and fructose
maltose
_ve
+ve
so it's glucose
so it's fructose
42
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
* Molisch’s Test:
Molisch’s Test is a sensitive chemical test for all carbohydrates, and some
compounds containing carbohydrates in a combined form, based on the
dehydration of the carbohydrate by sulfuric acid to produce an aldehyde
(either furfural or a derivative), which then condenses with the phenolic
structure resulting in a red or purple-colored compound.
Procedure:
1- In a test tube, add 2 ml of the test carbohydrate solution + 2 drops of
α-naphthol solution.
2- Carefully pour dropwise 1ml conc. H2SO4, using a dropper, on the
inner wall of test tube.
Observation:
A "violet colored ring" appears at the junction between the two layers.
1-
Fehling test :
1ml from Fehling reagent + 1 ml from sugar solution , and heat in positive
result it will give red brown precipitate.
*Fehling reagent = fehling A + fehling B
Fehling A = CuSO4.5H2O …
Fehling B = potassium sodium tartrate (also known as Rochelle salt)
2-
Barafoide test (test time) :
1 ml from Barafoide reagent + 1 ml sugar solution , then heat it will give a red
precipitate different in appearance time regard the sugar.
3-
Ozazone test :
1 gm solid sugar + 1 gm phenyl hydrazine hydrochloride + 1 gm sodium
acetate, then heat it in bath water above 20 min it will give a special structure
for every kind of sugar under microscope.
4-
Forfoural test :
1 gm solid sugar + 1 ml of conc.HCl, then heat until boiling and let vapors
contact with small paper which is moist by aniline acetate.
5-
Iodine test :
Starch solution + 1 drop from iodine , it has colored by blue color.
43
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
44
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Determine unknown organic substance
* physical properties :
Substance No.
Shape
color
Solubility in water
* chemical properties :
No.
Test
Observation
Inference
So this substance is : ………………………………………….
45
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
The Periodic Table of Elements
46
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
‫حمض‬
Acid
‫حمىضح‬
Acidity
Alkaline
‫لهىي‬
Amount
‫كميح‬
Analysis
‫ذحهيم‬
Anion
‫أويىن‬
‫ماء مهكي‬
Aqua regia
‫مائي‬
Aqueous
‫رسج‬
Atom
Atomic
‫رسي‬
Base
‫لاعذج‬
Basic
‫لاعذي‬
Basicity
‫لاعذيح‬
Beaker
‫كأط‬
Bond
‫ساتطح‬
Bonding
‫اسذثاط‬
Brush
‫فششاج‬
‫مىلذ إحرشاق‬
Bunsen Burner
‫حشق‬
Burn
Cation
‫كاذيىن‬
Charge
‫شحىح‬
‫خىاص كيميائيح‬
Chemical properties
‫كيمياء‬
Chemistry
47
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
‫كهىس‬
Chlorine
‫ذصىيف‬
Classification
Cold
‫تاسد‬
Colour
‫نىن‬
Combustion
‫إحرشاق‬
Concentrate
‫يشكض‬
Concentrated
‫مشكض‬
Concentration
‫ذشكيض‬
‫مادج آكهح‬
Corrosive
Crystalline
‫تهىسي‬
Crystals
‫تهىساخ‬
Decomposition
‫ذفكك‬
Density
‫كثافح‬
Detection
‫كشف‬
)‫داي (تادئح ذعىي ثىائي‬
DiDissociation
‫ذفكك‬
Dissolve
‫يزية‬
Divalent
‫ذكافؤ ثىائي‬
‫مضدوج‬
Double
‫ذأثيش‬
Effect
Electron
‫انكرشون‬
Element
‫عىصش‬
Flask
‫دوسق‬
‫فهىس‬
Fluorine
48
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Forceps
‫مهمظ‬
Formula
‫صيغح‬
‫اوصهاس‬
Fusion
‫غاص‬
Gas
‫مدمىعح‬
Group
Heterogeneous
‫غيش مرداوظ‬
Homogeneous
‫مرداوظ‬
Hydrolysis
‫ذحهم‬
Hydroxide
‫هيذسوكغيذ‬
‫غيش ومي‬
Impure
Index
‫دنيم‬
Inert
‫خامم‬
‫غيش عضىي‬
Inorganic
‫يىد‬
Iodine
‫أيىن‬
Ion
‫أيىوي‬
Ionic
‫مشكثاخ أيىويح‬
Ionic compounds
‫ذأيه‬
Ionization
‫معمم – مخرثش‬
Laboratory
‫خالخ انشصاص‬
Lead Acetate
‫عائم‬
Liquid
‫وسلح عثاد انشمظ‬
Litmus Paper
‫مادج‬
Material
49
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Medium
‫وعظ‬
Metal
‫معذن‬
Mineral
‫فهض‬
Mixture
‫خهيظ – مضيح‬
Molecule
‫خضيء‬
Neutral
‫معرذل‬
Oxidation
‫أكغذج‬
Oxide
‫أكغيذ‬
‫عامم مؤكغذ‬
Oxidizing agent
‫أوكغديه‬
Oxygen
Pipette
‫ماصح‬
Precipitate (ppt)
‫ساعة‬
‫تشوذىن‬
Proton
Pure
‫ومي‬
Radical
‫شك‬
Reactant
‫مادج مرفاعهح‬
Reagent
‫كاشف‬
Reduction
‫اخرضال‬
Sample
‫عيىح‬
Saturated
‫مشثع‬
‫محهىل مشثع‬
Saturated Solution
‫صهة‬
Solid
‫روتاويح‬
Solubility
50
T- Muataz Sufyan
Taiz University
Org. Chem. Lab.
Soluble
‫رائة‬
Solute
‫مزاب‬
Solution
‫محهىل‬
Solvent
‫مزية‬
Stable
‫ثاتد‬
Standard
‫لياعي‬
Sulfur
‫كثشيد‬
‫فىق مشثع‬
Super saturated
‫سمض‬
Symbol
‫خذول‬
Table
‫أوثىتح اخرثاس‬
Test Tube
Tin
‫لصذيش‬
Tri-
)‫ذشاي (تادئح ذعىي ثالثي‬
Unsaturated
‫غيش مشثع‬
Unsoluble
‫غيش رائة‬
Unstable
‫غيش مغرمش‬
Vapor
‫تخاس‬
Weight
‫وصن‬
‫خاسصيه – صوك‬
Zinc
‫مغحىق انخاسصيه‬
Zinc dust
51
T- Muataz Sufyan