Pharm. Chem. Dept.

Faculty of pharmacy
Delta University for Science and Technology

Notes in
Practical Organic Chemistry-I

Pharm.D. Clinical (CPC-102)

First Year - First Semester

By

Staff Members of Pharmaceutical Chemistry

0
Contents

laboratory Safety Rules and Practices ............................................. 3

Organic Lab Equipment .................................................................... 7

General Scheme for Identification of Organic Compounds .......... 9

A) Physical Characteristics ............................................................... 9

B) Chemical reactions ...................................................................... 20

(1) Action of soda lime ..................................................................... 20

(2) Action of sodium carbonate solution ........................................ 28

(3) Action of Na2CO3 ........................................................................ 32

)4) Detection of elements other than C, H, or O ............................ 36

Qualitative Organic Chemistry ....................................................... 42

1) Alcohols (ROH) ............................................................................ 42

2) Aldehydes & Ketones ................................................................... 51

3) Carboxylic Acids .......................................................................... 60

1
 Student Name

Student ID.

Lab. No

Attendance sheet

No Subject Date Signature

- Laboratory Safety rules

1.
- Physical characters
2. - Action of Soda lime

- Action of sodium carbonate

3.
- Elements tests

4. - Action of ferric chloride

5. Exam

6. - Alcohols

7. - Aldehydes and ketones

8. - Aliphatic acids and their salts

9. - Aromatic acids and their salts

10. Revision

11.
Practical Exam
12.

2
 LABORATORY SAFETY RULES AND PRACTICES

❖ Safety in the laboratory is an extremely important element in the

chemistry program at this university.
❖ Failure to follow safe practices can cause laboratory accidents which may
result in the loss of time, damage to clothing and other property, and most
importantly personal injury.
❖ By following suitable precautions, you can anticipate and prevent
situations that would lead to accidents.
❖ You must become thoroughly familiar with the information in the
following sections.

A) PERSONAL PROTECTION

1. You may work in the laboratory only if the teaching assistant is present.
2. You must work only on authorized experiments.
3. You must wear proper eye protection and a lab coat in the laboratory
whenever any laboratory work is in progress.
4. You must not wear contact lenses in the laboratory.
5. You must wear shoes which do not have open spaces; sandals and open-
toe shoes are not acceptable.
6. You must not eat, drink in the laboratory. You must not even bring food
or drink into the laboratory.

3
7. You must confine long hair and neckties. You must cover frilly or flared
clothing with a lab coat. (Loose jewelry may also be a hazard.)
8. You must not engage in acts of carelessness while in the laboratory.
9. You must work carefully with a full awareness of what you are doing in
order to avoid breaking equipment or spilling chemicals.

B) PROPER LABORATORY PRACTICES

1. Carefully read the label on a bottle twice before using its contents.
2. Take only the quantity of reagent needed. Never return an unused reagent
to its container.
3. Mix reagents only when specifically directed to do so.
4. Never place chemicals directly on the balance pan. Weigh reagents using
a beaker, flask or weighing paper.
5. If instructed to observe the odor of a chemical, do so by fanning air over
the container toward your nose. Do not smell the substance directly.
6. Never taste any chemicalsor reagents.
7. Avoid handling chemicals directly with your hands unless directed to do
so. If contact occurs, immediately flush the area with cool water.
8. Use a bulb or a pipetting device to draw liquids into a pipette. Never
pipette by mouth.
9. When diluting strong acids or strong bases, the acid or base should be
added to the water, not vice versa.
10.Before igniting a Bunsen burner, make sure no flammable liquids or
vapors are in the area.
11.Heat test tubes at the surface of the liquid. Agitate the tube. Be sure to
slant its open end away from other people.
12.Stay clear of an open vessel in which a process is occurring that could
produce spattering.

4
 13.Keep reagents and equipment well back from the edge of the lab bench.
14.Do not use cracked glassware, as it may break when stress is put on it.

C) ACCIDENTS AND INJURIES

❖ Report all accidents and injuries to the teaching assistant as soon as

possible.
❖ You will also have to complete an Accident Report form at the
stockroom.
❖ First Aid kits with some supplies and latex gloves are located in each
laboratory.
❖ In the event of an injury, some basic first aid procedures to be followed
immediately include:
1. Skin burns: Place the affected area immediately under cold running tap
water for 10 minutes to remove the heat or irritant.
2. Chemicals in Eyes: Flush your eyes with water at the eyewash for at least
15 min.
3. Hair or Clothing Fires: Use the safety shower to extinguish flames.
D) Fire and explosion precautions

If flames are used, observe the following precautions:

❖ Never heat an inflammable liquid in an open container.
❖ Never pour inflammable liquids from one container into another within
several feet of a flame.
❖ Work only in a properly operating chemical fume hood.

E) In Case of FIRE Accident

❖ Your first consideration is to avoid any danger.

❖ Notify your instructor immediately.
❖ To help prevent spread of the fire, remove any containers of flammable

5
 solvents from the area and turn off any burners, if this is possible.
❖ If your clothing is on fire, do not run; rapid movement will only fan the
flames.
❖ Roll on the floor to smother the fire and to help keep the flames away
from your head.
❖ If burns are minor, apply a burn ointment. In case of serious burns, do not
apply any ointment but visit hospital at once.
F) Chemical burns

❖ Areas of the skin with which corrosive chemicals have come in contact
should be immediately washed thoroughly with water.
❖ If the burns are minor apply burn ointment; for treatment of serious
burns, see a physician.
❖ Apply cod liver oil ointment and a dressing.
❖ If chemicals particularly corrosive or hot reagent came in contact with the
eyes immediately flood the eyes with water. A specially designed eye
wash fountain is useful.
❖ Do not touch the eye. The eyelid as well as the eyeball should be washed
with water for several minutes.
❖ If the injury appears to be serious, see a physician as soon as possible.

G) Chemical Hazards and Symbols

6
Organic Lab Equipment

7
8
 GENERAL SCHEME FOR IDENTIFICATION OF ORGANIC
COMPOUNDS
A) Physical Characteristics
1- Condition
Any organic compound may be a gas, liquid or solid.
Solid organic compound
• If the substance is solid, examine a few particles on a watch glass and notice
whether it is crystalline, amorphous or fine powder.
• The crystalline compound possess a definite shape which may be plates,
prisms, needles or in the form of microcrystalline powder.
N.B. Hygroscopic substance: Substance has the ability to absorb water.
Liquid organic compound
The liquid compounds may be mobile e.g. methyl and ethyl alcohol or viscous
e.g. glycerol and lactic acid.
2- Color
• The color of the original sample must be noted. Simple aliphatic and
aromatic compounds with single functional groups tend to be colorless,
whereas aromatic compounds with both electron-donating and electron
withdrawing groups in conjugation with each other tend to be strongly
colored.
• Many organic compounds, particularly aromatic ones, show color due to
impurities (this is produced mainly as a result of their slow oxidation by
air. e.g. aniline is colorless and on standing it converted into brown
color).
• The colors are due to the presence of chromophoric group e.g. nitro
group (NO2), carbonyl group (C=O), azo group (N=N), ….. etc (usually
indicating extended conjugation in the molecule).
• When such groups are introduced into a molecule, absorption maxima

9
 are shifted towards the visible region and the substance appears colored.
A group that increases the color in the molecule is known as
auxochroms e.g. hydroxyl group (OH), amino group (NH2).

A summary of the color is shown in the following

Color Expected substance (s)

Orange red Nitroaniline, Azo compounds
Brown Higher aromatic amines
Pink Naphthols
Yellow Nitro compounds, Iodoform
Colorless turns to reddish brown or pink Phenols, Aniline, Aminophenols,
(air oxidation) α,β-naphthylamines.
Colorless turns to yellow or yellowish
Anthracene, Cinnamic acid, Cresol
brown

The color of an organic compound is due to the transmitted color (complementary

color) not the absorbed color. As example, the green color of plant leaf is due to
the leaf absorb all the color and transmits the complementary color only (green).
The next table indicates the correlation between the absorbed and the transmitted
light.
3-Odor
Many types of organic compounds have characteristic odors. Therefore,
the ability to detect odors and to be familiar with it is very helpful in
their identification. Some compounds and their common odor are listed in
the following table.
Odor Expected substance (s)
Bitter almond odor Benzaldehyde, Nitrobenzene, Benzyl alcohol.
Mice like odor Acetamide
Oil of winter green Methyl salicylate
Apple like odor Ethyl acetate
Pleasant sweety Chloroform, Carbon tetrachloride
Phenolic Many phenols

10
 Pungent; irritant Formic acid, Formaldehyde, Chloral hydrate.
Vinegar like odor Acetic acid
Ammonia odor Aliphatic amines
Fishy odor Aromatic amines
Alcoholic odor Ethanol, Methanol
Carbohydrates, aromatic acid, solid aliphatic acids, all
Odorless
salts of aromatic and aliphatic acids, glycerol, urea

4- Solubility/Miscibility characteristics
Determination of the solubility or miscibility characteristics of an organic
compound can often give valuable information about its structure.
Several schemes have been proposed to place a substance in a definite
group according to its solubility or miscibility as indicate d in the next
scheme.
N.B. The term Solubility is used for solid compound, while miscibility is
used for liquid compound.
In doing the solubility tests follow the next scheme in the order given.
Keep a record of your observations.
• Step I Test for solubility/miscibility in water.
If soluble, test the solution with litmus paper.
If it is immiscible (in case of liquid), density of the immiscible liquid
should be recorded whether it is lighter or heavier than water.
• Step II Water-insoluble compounds are tested for solubility in a 10%
NaOH aqueous solution.
If soluble, determine the solubility in NaHCO 3 aqueous solution.
• Step III Test for solubility in NaHCO3 aqueous solution.
if it is soluble, so the compound is strong acid.
if it is insoluble, so the compound is weak acid.
• Step IV Compounds insoluble in 10% NaOH aqueous solution are
tested for solubility in dil. HCl solution.

11
 • Step V Compounds insoluble in dil. HC1 solution are considered
insoluble in all reagent
a) Solubility or miscibility in water:
Place the compound (0.1-0.2 gm or 0.3 ml) in a test tube, add 5 ml H 2O
and shake-well at room temperature. Record your results. If the compound
completely soluble or miscible. Test the aqueous solution with litmus
paper and observe whether it is neutral, basic or acidic.
If the unknown substance is liquid and miscible with water. Test the
liquid with anhydrous CuSO 4 (white) and observe whether the unknown is
true liquid or aqueous solution through change the color of anhydrous
CuSO 4.
1. If the white color of CuSO 4 changed to blue, the unknown may be
aqueous solution, i.e. the compound is diluted with water.
2. If the white color of CuSO 4 unchanged, the unknown may be true
liquid, i.e. the compound is pure and not containing water.
If the unknown substance is liquid and immiscible with water the
density of the immiscible liquid should be recorded whether it is lighter
or heaver than water.
b) Solubility or miscibility in 10% sodium hydroxide:
If the unknown substance is insoluble in water, try its solubility in dil.
sodium hydroxide (10%). If it is soluble add conc. HC1 and examine
carefully any sign of separation for the original unknown which
indicates acidic substance.
Observation Expected product (s)

Aromatic carboxylic acids, higher

Soluble in dil. NaOH and aliphatic acids, aromatic amino
re-precipitate by conc. acids. acids, sulfonic acids, and
polynitrophenols.

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c) Solubility in sodium bicarbonate solution.
This test should be carried out for acidic substance. Add few crystals or few
drops of the unknown substance to a test tube containing 2 mL of dil. NaHCO3
and mild shake of the test tube. Note the solubility and any effervescence. If
soluble with effervescence of CO2, the unknown is strong acid e.g. aromatic acid,
sulphonic acid, and nitrophenols. If it is insoluble and no effervescence of
CO 2 , the unknown is weak acid e.g. phenols, and imides.

IV) Solubility or miscibility in dil. hydrochloric acid:

If the substance is insoluble in water and dil. NaOH solution, try its solubility
in dil. HC1. If the substance is soluble and re-precipitates again by adding 30%
NaOH solution it is classified as basic substance e.g. monoarylamines (aniline
and toluidines).
N.B If the substance is soluble in dil. NaOH and not reprecipitated by conc. HCl,
meanwhile, it is soluble in dil. HCl but not re-precipitated by NaOH, these
compounds are classified as amphoteric compounds, e.g. amino acids.

13
Unknown No. Date: / /

A- Physical Characters:
1- Condition:

2- Color:

3- Odor:

4- Solubility/Miscibility

a- H2O
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:

b- NaOH (10%) Comment:

c- NaHCO3 Comment:

d- Dil. HCl Comment:

14
Unknown No. Date: / /

A- Physical Characters:
1- Condition:

2- Color:

3- Odor:

4- Solubility/ Miscibility

a- H2O
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:

b- NaOH (10%): Comment:

c- NaHCO3 Comment:

d- Dil HCl: Comment:

15
Unknown No. Date: / /

A-Physical Characters:
1- Condition:

2- Color:

3- Odor:

4- Solubility/ Miscibility

a- H2O
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:

b- NaOH(10%): Comment:

c- NaHCO3 Comment:

d- Dil HCl: Comment:

16
Unknown No. Date: / /

A-Physical Characters:
1- Condition:

2- Color:

3- Odor:

4- Solubility/ Miscibility

a- H2O
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:

b- NaOH(10%): Comment:

c- NaHCO3 Comment:

d- Dil HCl: Comment:

17
Unknown No. Date: / /

A-Physical Characters:
1- Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

18
Unknown No. Date: / /

A- Physical Characters:
1- Condition:

2- Color:

3- Odor:

4- Solubility/ Miscibility

a- H2O
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:

b- NaOH(10%): Comment:

c- NaHCO3: Comment:

d- Dil HCl: Comment:

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 B. Chemical reactions
(1) Action of soda lime
Soda lime is a fused mixture of sodium hydroxide (NaOH) and calcium
oxide (CaO). Its main function is based upon the action of sodium hydroxide
itself, while CaO decompose or dehydrate the substance.
Procedure:
Step-1: Mix one part of the substance with three parts of soda lime and
triturate this mixture with grinding in a dry porcelain mortar. The odor of
ammonia on cold (without heating) usually indicates an ammonium salt, and
sweat odor of chloroform indicates chloral hydrate, while the fishy odor of
aniline indicates aniline salt.
Step-2: Place the mixture in a dry test tube and add another layer of soda
lime of the same thickness then heat the test tube from up to down. The
upper layer of soda lime acts as a safe guard against escape of any unreacted
substance.
Mode of action of Soda lime:
Hydrolyzing agent:
a) Ammonium salts give ammonia odor on cold when triturated with soda
lime. You can smell it upon trituration in the mortar (it turns moist red litmus
paper blue).

b) Soda lime acts on amides and imides upon heating to give ammonia odor.

• Phthalimide and benzamide give, in addition to ammonia, bitter

almonds odor due to the formation of benzonitrile with soda lime upon

20
 heating.

c) Aniline salts give fishy odor of aniline on cold when triturated with soda lime.

d) Anilindes (e.g. acetanilide and benzanilide) give fishy odor of aniline upon
heating when triturated with soda lime.

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Decarboxylation:
a) Benzoic acid, phthalic acid, and their metallic salts (sodium or potassium) give
the odor of benzene on heating. Salicylic acid or its salts give the odor of
phenol. Cinnamic acid yields styrene odor (pleasant odor).

Dehydrating agent :
Burnt sugar odor is produced when carbohydrates and some hydroxy
aliphatic acids such as tartaric, and citric acids or their salts are heated
strongly with soda lime.
* Salts of lactic acid (solid) give also, burnt sugar odor when are heated
strongly with soda lime.
* Ammonium salts of hydroxy aliphatic acids give ammonia odor on cold
when triturated with soda lime due to hydrolysis while, it gives burnt
sugar odor when are heated strongly with soda lime due to
dehydration.

22
Unknown No.: Date: / /
A-Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:

23
Unknown No.: Date: / /
A-Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:

24
Unknown No.: Date: / /
A-Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:

25
Unknown No.: Date: / /
A-Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:

26
Unknown No.: Date: / /
A-Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:

27
(2) Action of sodium carbonate solution
Procedure: Place about 2 ml of dilute Na 2 CO 3 solution in a clean
test tube, and then add few drops or few portions of the sample.
Observe any effervescence on the surface of the solution.
Effervescence indicates that carbon dioxide has been evolved which
means that the sample compound is stronger acid than carbonic acid .
The following classes of compounds cause effervescence with sodium
carbonate solution with evolution of CO 2 gas:

a) Carboxylic and Sulfonic acids (but not phenols, so this reaction can be
used to distinguish between true acids and phenols).

b) Salts of weak bases e.g. aniline sulfate and aniline hydrochloride which
hydrolyses in aqueous solution to aniline which appear as white
emulsion separated into oily droplets and free acid (H 2 SO 4 or HCl).

c) Nitrophenols: In these compounds the nitro group enhances the acidic

properties of the phenolic group which become stronger acid than
carbonic acid and is thus able to liberate CO 2 from sodium carbonate
solution.

28
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

29
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

30
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

31
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:

3) Action of Na2CO3: Comment:

32
(3) Reaction with aqueous ferric chloride solution:

Generally, Ferric chloride (FeCl 3 ) solution usually contains a large

excess of HCl, due to the method of preparation, which interfere with
the reaction product. Therefore, a neutral solution of ferric chloride
should be prepared by adding dilute NaOH solution, drop by drop, to the
ferric chloride solution until a little but permanent precipitate of ferric
hydroxide is obtained. The solution is then filtered off and the clear
filtrate is used. Characteristic colors or colored precipitates are
frequently given by the reaction of ferric chloride solution with:
a) Solutions of neutral salts of acids.
b) Phenols.
c) Amines.
The color produced with these compounds may be, either due to:

1) The formation of ferric salts of acids. These ferric salts of organic

acids are salts of weak acids that dissolve in mineral acids. Therefore,
the presence of HCl in excess with the reagent will dissolve these
salts. The reaction of neutral FeCl 3 with oxalic acid gives lemon yellow
color of ferric oxalate. In case of using FeCl 3 without neutralization, the
ferric oxalate will dissolve in HCI with the formation of oxalic acid
again. It means that, neutral solution of FeCl 3 must be prepared in case of
reaction with free acids.

33
2) The oxidation effect of FeCl3, in case of phenols and amines, giving colored
oxidation products. This redox reaction may need acidic pH to go smoothly
towards the formation of this colored oxidation product. Therefore, the
neutralization step for FeCl3 is not recommended in such case.

Place about 0.2 g of the acid in a test tube and a slight excess of ammonia
solution is added i.e. until the solution is just alkaline to litmus paper.
The solution is then boiled, until the odor of ammonia is completely
disappeared, and then cooled. To the neutral solution of acid obtained,
add a few drops of the neutral ferric chloride solution. Compare the color
produced with that of water and few drops of FeCl 3 solution (control
test).
N.B: Unless all the excess ammonia has been evaporated in the
preparation of the neutral salt, the result obtained on adding ferric
chloride will be misleading owing to the precipitation of ferric hydroxide
a) Lower aliphatic acids as formic and acetic acids give deep red color
(blood red) which on boiling yield brown precipitate of the basic ferric
salt, which on adding dil. HCI it dissolves to give a clear solution.

b) Oxalic acid gives a lemon-yellow color.

c) Aromatic nonphenolic carboxylic acids e.g. benzoic acid, phthalic and
cinnamic acid, give buff colored precipitate, which dissolves in dil. HCI with
the production of a white precipitate of the free acid.

34
d) Salicylic acid yields violet color. A dilute solution of salicylic acid will
give this color without neutralization.
e) Hydroxy aliphatic acids e.g. lactic, tartaric and citric acids yield dark
yellow color in neutral solutions (a blank test should be done).
f) In case of aromatic amines, dissolve few drops or a few crystals of the
amine in dil. HCI then add few drops of FeC13 without neutralization and
observe the color obtained on cold with occasional shaking and then apply
heating and observe whether the color changed or still present.
g) In case of phenols, make a very dilute aqueous or alcoholic solution and
add ferric chloride solution. Most phenols form colored complexes in the
presence of ferric ion Fe +3, in which six molecules of a monohydric phenol
are combined with one atom of iron to form a complex anion. Most
phenols produce red, blue, purple, or green color. Sterically hindered
phenols give negative tests. Aliphatic enols (ethyl acetoacetate,
acetylacetone) give a positive test.

N.B: The above chemical reactions of identification are applied to see further
information about the nature of the unknown concerning the presence or
absence of common functional groups. These tests must be performed accurately
and careful observations should be made. If the observation is doubtful, you
should carry out a control test. Thus it is possible to make direct and immediate
comparison between the results of the experiments. It is very important to
observe which positive and negative tests look like.

35
)4) Detection of elements other than carbon, hydrogen, or
oxygen.

The elements other than C, H and O that are most often present in organic
compounds are nitrogen, sulfur, and halogens (X = F, Cl, Br or I). To detect the
presence of these elements, the organic compound is generally fused with
metallic sodium. This reaction converts these heteroatoms to the water-soluble
inorganic compounds NaCN, Na2S and NaX. By using inorganic qualitative tests
enable us to detect the presence of the corresponding anions.

36
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

4) Action FeCl 3 : Comment:

5) Element Test: Halogen ( ), N ( ) and S ( ).

37
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

4) Action FeCl 3 : Comment:

5) Element Test: Halogen ( ), N ( ) and S ( ).

38
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

4) Action FeCl 3 : Comment:

5) Element Test: Halogen ( ), N ( ) and S ( ).

39
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

4) Action FeCl 3 : Comment:

5) Element Test: Halogen ( ), N ( ) and S ( ).

40
Unknown No.: Date: / /
A) Physical Characters:
1- Condition:
2- Color:
3- Odor:
4- Solubility/ Miscibility
a- H2O:
Litmus Paper: Comment:
Anhydrous CuSO 4: Comment:
b- NaOH (10%): Comment:
c- NaHCO 3 Comment:
d- Dil. HCl: Comment:

B) General Reactions:
1) Action of Soda lime:
On Cold:
On Hot: Comment:
2) Action of 30% NaOH:
On Cold: Comment:
On Hot: Comment:
3) Action of Na 2 CO 3 : Comment:

4) Action FeCl 3 : Comment:

5) Element Test: Halogen ( ), N ( ) and S ( ).

41
 Qualitative Organic Chemistry
1) Alcohols (ROH)

An alcohol is a compound that contains one or more hydroxyl groups i.e alcohols are
hydroxy derivatives of the alkanes. They are classified into primary, secondary or tertiary
depending on whether the hydroxyl group attached to primary, secondary or tertiary carbon
atom.

H H R``

R C OH R C OH R C OH
H R` R`
Primary Secondary Tertiary

Also they are classified according to the number of hydroxyl groups into monohydric,
dihydric, trihydric and polyhydric alcohols.

OH CH2OH
Methanol CH3OH CH2OH

Ethanol C2H5OH H OH
CH2OH
n-Butanol C4H9OH
Glycerol Cyclohexanol Benzyl alcohol
Physical Characters
* All are colorless liquids
* Glycerol is odorless, benzyl alcohol has a faint bitter almond odor and other alcohols have
faint odor.
* Alcohols form strong intermolecular hydrogen bonds, the lower-molecular weight alcohols
can readily replace water molecules in the hydrogen-bonded network.

R R H R H
O H ........ O H O H ........ O H ....... O H

42
This hydrogen bonding accounts for the miscibility of much alcohol in water.
* Methyl alcohol, ethyl alcohol, glycerol are freely miscible with water.
* N-Butanol is lighter than water (if add excess alcohol) but miscible in excess water
GENERAL REACTIONS OF ALCOHOLS
(1) Esterification:
Alcohols form esters when treated with acyl halides or with carboxylic acids in presence
of a dehydrating agent such as conc. sulfuric acid. The products are usually pleasant smelling
ester.

O +
1 H 1
ROH + R C OH RCOOR + H2O
alcohol acid ester

Add to a mixture of 0.5 ml of alcohol and 0.5 g of the carboxylic acid or its salt, about 2ml
of conc. sulfuric acid. Heat gently for 2 minutes and then pour into sodium carbonate solution
(2g. in 100 ml of water) in order to decompose the acid vapours and to get a more clear odor.
The ester will be separated as oil droplets.
(2) Oxidation:
Alcohols are readily oxidize with potassium dichromate and sulfuric acid or with
potassium permanganate in presence of sodium carbonate.

Take about 5 ml of the alcohol, add to it 5 ml of strong solution of K2Cr2O7 and 2 ml of

conc. H2SO4. Boil the mixture under reflux for about five minutes. A positive test is
indicated by a color change from orange to the blue green. Or, take 1 ml of the alcohol, add to
it 3 ml of KMnO4 solution and 0.3 g of Na2CO3 solid. Boil the mixture for about 2 minutes,
The color of KMnO4 disappears.

43
 SPECIAL TESTS
1) METHANOL
CH3OH
It is a mobile colorless liquid (Bp = 64.5º) with a characteristic alcoholic odor. It catches fire
easily and burns with non-luminous flame.
1- Esterification:
By esterifying salicylic acid with methanol in presence of conc. H2 SO4, the characteristic
oil of winter green odor of methyl salicylate is detected on pouring into sodium carbonate
solution.

OH OH
COOH COOCH3
+ CH3OH + H2O

Salicylic acid Methanol Methyl salicylate ester

Oil of winter green odor
- Ethanol gives ethyl salicylate which has a similar but fainter odor.

2) Oxidation:

[O]
CH3OH HCOOH

Methanol could be oxidized completely into formic acid using alkaline KMnO4. Formic acid
could be distilled over in a test tube containing dil. ammonium hydroxide. The solution is
boiled to drive off the excess ammomia and the neutral solution is tested for formate with
neutral FeCl3 solution, and by its reduction of Hg Cl2 solution.
2) ETHANOL
C2H5OH
It is a colorless mobile liquid with characteristic alcoholic odor (Bp78.5º)
1) Esterification:

conc.
CH3COOH + C2H5OH CH3COOC2H5 + H2O
H2SO4

44
 Esterification of ethanol could be carried out using glacial acetic acid or sodium acetate in
presence of conc. H2SO4. Notice the agreeable fruity odor (apple-like odor) of ethyl acetate.
The odor of methyl acetate is similar to ethyl acetate but fainter in odor, it is therefore
impracticable to attempt to distinguish methanol and ethanol by this test alone.
2) Oxidation:
Oxidation of ethanol is carried out with pot.dichromate and sulfuric acid the characteristic
odor of acetaldehyde is produced at this stage and the solution turns green. The acetaldehyde,
can be distilled over, collected in water and tested by Schiff`s reagent. Continue to heat for 3
minutes and distill off a few ml. Test the distillate with blue litmus paper to show that it is
definitely acid. Then apply test for acetic acid.
3) Iodoform test:
Compounds containing CH3CO- or CH3CHOH- linkage attached to carbon or hydrogen
give a positive haloform reaction e.g. methyl ketones and methyl carbinols.

O
R C CH3 +3I2 + NaOH RCOONa + CH I3
Iodoform

O O
- -
R C CH3 + 3 I2 + 3 OH RCCI3 + 3H2O + 3 I
-
O O
-
R C C I3 + OH R C CI3
OH

O
O
- -
RC O + CHI3 R C OH + C I3

To 1 ml of the alcohol add 3 ml of 10% NaOH solution. Add iodine solution little by little
till a persistent yellow color is given. Warm gently for 1-2 minutes. The pale yellow crystals
of Iodoform should be apparent.

45
 3) BENZYL ALCOHOL
CH2OH

It is colorless oily liquid, immiscible with water, with faint odor of bitter almonds.
(1) Esterification:
By esterifying benzoic acid with benzyl alcohol in presence of conc. sulfuric acid, the
fragrant odor of benzyl benzoate is detected on pouring into sodium carbonate solution.
(2) Action of conc. sulfuric acid:
To 0.5 ml of benzyl alcohol add 0.5 ml of conc. H2SO4 and shake the mixture. Heat is
evolved and a greenish white gelatinous polymer gradually separates.

4) GLYCEROL
CH2OH
H OH
CH2OH
It is viscous liquid, with sweet taste, very hygroscopic miscible with water and alcohol
(Bp=290 ºC with decomposition) glycerol contains one secondary and two primary alcoholic
groups.
(1) Borax test:
Boric acid is a very weak acid. So borax solution is alkaline due to hydrolysis into a strong
base and a weak acid.
Na2B4O7 + 7H2O → 2NaOH + 4B(OH)3

If you add glycerol to the solution of borax it will react with boric acid giving glyceroboric
acid complex which is strong acidic
CH2OH CH2OH
H O O H
B H
H O O H
H H

Glyceroboric acid

Prepare a dilute solution of borax and few drops of ph.ph., when a pink color is produced,
add few mls of glycerol then the color will fade. On heating the color appears again and fades
on cooling.

46
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S

( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

47
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

48
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

49
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

50
2) Aldehydes & Ketones
A) Aldehydes
RCHO

HCHO CH3CHO
formaldehyde Acetaldehyde

CCl3CH(OH)2
CHO
chloral hydrate
benzaldehyde
Physical Characters
* Formaldehyde is a colorless gas, it is provided in the form of 40% aqueous
solution which has a characteristic pungent odor and known as formalin.
* Acetaldehyde is a liquid b.p.20 ºC, usually used in aqueous solution as it is
miscible with water in all proportions. It has a characteristic disagreeable odor.
In dilute aqueous solution, it has apple-like odor. Aqueous solutions of
formaldehyde and acetaldehyde sometimes are slightly acidic due to partial
oxidation with atmospheric oxygen.
* Benzaldehyde is a colorless liquid, bp.179 ºC, immiscible with and heavier
than water. It has a characteristic odor of bitter almonds.
GENRAL REACTIONS OF ALDEHYDES
(1) Reduction of ammoniccal silver nitrate:
Place about 3 ml of silver nitrate solution in a clean test tube and add few
drops of dil. NaOH solution. Add dil. ammonia solution drop by drop until the
formed ppt. of silver oxide is almost redissolved. Then add few drops of the
aldehyde and heat for a few minutes on a water bath. A silver mirror is formed.
Aldehydes are sensitive to oxidizing agents, one of these is AgNO 3
solution in presence of NH4OH, where a complex ion is formed which is

51
Ag(NH3)2+. The aldehyde is oxidised to the corresponding carboxylic acid
which will be fixed as its ammonium salt and the complex silver ion is reduced
to metallic silver which form a mirror on the wall of the test tube.

RCHO + 2Ag (NH3)-2+ 2OH- .3O + 3NH2+ H 42Ag + RCOO NH→

(2) Fehling's Solution:

Fehling's solution is made by mixing Fehling A (CuSO 4 solution) with

Fehling B (alkaline solution of Roschel salt). This combination results in a deep

blue solution containing a complex cuppric ion and on interaction with
aldehyde, the copper is reduced to univalent state with precipitation of Cu 2O.

RCHO + 2Cu++ + NaOH + H2O → RCOONa + Cu2O + 4H+

Aliphatic aldehydes in aqueous solutions are usually acidic owing to

atmospheric oxidation, and therefore frequently fail to reduce Fehling's solution,
since the alkali of the latter is neutralized by the acid present. On the other hand,
an excess of Fehling's solution is not recommended, as the blue color of
Fehling's solution may then mask the ensuing reduction. Thus, it is advisable to
add sod. carbonate solution to the aldehyde at first.
Add about 1 ml. of 10% Na2CO3 solution to an equal volume of the

aldehyde. Add a few drops of Fehling's solution and boil the mixture gently on a
water bath.
The solution usually turns green and on standing a red ppt. of cuprous oxide
slowly separates.
(3) Action of sodium hydroxide:
Aliphatic aldehydes with the exception of formaldehyde when treated with
30% NaOH solution give the aldehyde resins which are yellow and possess a
characteristic odor of bad apples.
Formaldehyde and aromatic aldehyde undergo Cannizzaro's reaction i.e. self
oxidation reduction.

52
 30% Na OH
2 HCHO CH3OH + HCOO Na
30% Na OH
2C 6H5CHO C 6H5CH2OH + C 6H5COO Na

a- Warm 1 ml of acetaldehyde solution with 2 ml. of 30% NaOH solution, a

yellow resin is obtained.
b- Reflux 2 ml of benzaldehyde with 4 ml of 30% NaOH solution for 15
minutes. Add sufficient water to dissolve the sod. benzoate which has been
formed. Add concentrated hydrochloric acid, a white precipitate of benzoic acid
is obtained on cooling.
In case of formaldehyde, formic acid could be distilled after acidification.
(4) Oxidation:
Warm a mixture of 0.5 ml of benzaldehyde and 15 ml of saturated KMnO 4
solution and 0.5g. of Na2CO3. Acidify with conc. HCl and add 25% sod.
sulphite solution until the precipitated manganese dioxide has redissolved. On
cooling benzoic acid crystallises out.
(8) Special test for formaldehyde:
To 0.5 ml. of formaldehyde solution add 2g. of salicylic acid and one ml of
conc. H2SO4 on the wall of the test tube, a crimson red color is produced.

(9) Special tests for acetaldehyde:

a- Nitroprusside reaction:
Add I ml of the freshly prepared solution of sod. Nitroprusside to about 2 ml.
of acetaldehyde solution. Add about 10 ml. of dil.NaOH solution, when a
reddish violet coloration is produced (No color is obtained in case of
formaldehyde).
b- Iodoform test:
Add about 5 ml of a dil. solution of NaOH to about I ml of acetaldehyde. Add

53
iodine solution little by little till a persistent yellow color is obtained. Warm
gently for a few minutes, to obtain a pale yellow crystals of iodoform.
CH3CHO + 3I2 + 3NaOH → CI3CHO+ 3NaI + 3H2O

CI3CHO + NaOH → CHI3 + HCOONa

B) KETONES

COCH3 CO
CH3COCH3
Acetone acetonphenone benzophenone

Physical characters:
* Acetone is a colorless liquid, bp. 56°, with characteristic odor, miscible with
water and its aqueous solution is neutral to litmus.
* Acetophenone is a colorless liquid, bp. 202°, mp. 20° , sparingly soluble in
water, and possesses a faint odor.
* Benzophenone is a colorless solid mp. 49° with characteristic odor, insoluble
in water.
GENERAL REACTIONS OF KETONES:
(1) Iodoform reaction:
Add 5 ml of 10% solution of sodium hydroxide to 1 ml of acetone. Add
iodine solution little by little till a persistent yellow color is obtained. Warm
gently if necessary. Pale yellow precipitate with characteristic odor of iodoform
is formed on the cold.
Acetophenone similarly gives iodoform, but the mixture must be shaken
vigorously due to the slight solubility of acetophenone in water. Benzophenone
does not give iodoform.
RCOCH3 +3I2 +4NaOH → CHI3 + RCOONa +3NaI+H2O

54
(5) Nitroprusside test:
Add 1 ml. of freshly prepared solution of sodium nitroprusside to 1ml. of
acetone or acetophenone. Add dil, sodium hydroxide solution in excess, to
obtain a red coloration.
(3) All ketones fail to reduce amm. silver nitrate solution or Fehling's solution
(distinct from aldehydes).

55
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

56
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

57
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

58
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

59
3) Carboxylic Acids
Members of this group are characterized by the presence of a crarboxyl
group in the molecule. The acid character is due to the presence of a replaceable
hydrogen atom in the carboxyl group which could be replaced by a metal
forming a salt.
General reactions of carboxylic acids

1- Solubility in alkali hydroxide:-

All acids dissolve readily in NaOH. The solubility in sodium hydroxide is a
great evidence for the acidity of these compounds. Aromatic acids soluble in
NaOH (insoluble in H2O) and reprecipitate on acidification.

2- Solubility in sodium carbonate solution:

Strong acids soluble in and decompose Na 2CO3 solution with evolution of
CO2.

RCOOH + Na2CO3 → RCOONa + CO2 + H2O

To carry out this tests:

a- For acids soluble in H2O:
Dissolve 1g of the unknown acid in 5ml of water followed by adding 1g of
sodium carbonate on the surface of the solution.
b- For acid insoluble in H2O:
Dissolve 1g of Na2CO3 in 3ml of H2O and boil untill bicarbonate present is
converted into carbonate and to remove any CO 2. Add the acid gradually and
observe the effervescence with evalution of CO2.
3- Decarboxylation with soda lime:
In a dry mortar triturate 1g of the acid and 1g of soda lime. You have to put
0.5g of the mixture between two layers soda lime (0.25 g each). Heat from

60
bottom to top, and smell the odor of the produced parent hydrocarbon .
4- Esterification:
Add 1ml of the alcohol (methyl or ethyl) to 0.5g of the acid in a dry test
tube. Add a few drops of conc. H 2SO4 and heat gently in the presence of
brocken glass. Cool the mixture and pour into a solution of sodium carbonate.
Notice the fragrant odor of the produced ester.
5- Action of Ferric choride (FeCl3):
The neutralized acids give with a neutral FeCl 3 solution characteristic color
or precipitate:
a- Neutralization of the acid:
In a test tube add 0.5 g of the acid followed by slight excess NH 3 solution
till the solution is just alkaline to litmus. Boil the solution until ammonia odor is
completely removed.
b- Neutralization of FeCl3 solution:
To 5ml FeCl3 in a test tube, NaOH (dil.) is added dropwise, until a small
but permanent turbidity of Fe (OH)3 is obtained. Filter the reaction mixture
from Fe (OH)3 and the clear filtrate is used.
Formic Acid; Methanoic acid
HCOOH
Mol. wt. 46.03, b.p. 100.7°C (volatile liquid), m.p. 8.4°C, solubility: water,
alcohol, ether, acetone, benzene. It has pungent odor.
1- Reduction of permanganate:
a- In acid medium:
To a solution of formic acid (2ml) or formate (1g) in water (5ml), 2ml of dil
H2SO4 is added. Few mls of dil solution of KMnO 4 is added drop by drop.
Observe the decolorization.
b- In alkaline medium:
Dissolve 0.2g of the acid or its salt in 10ml of 10% Na2CO3 solution and

61
 add dilute solution of KMnO 4 dropwisely. Notice the decolorization and
simultaneous precipitation of manganese dioxide.
2- Mercuric choloride:
Warm a few mls of HgCl2 solution with formic acid or its salt to give a
white ppt. of mercurous chloride. On adding excess formic acid metallic
mercury will precipitate as gray or black ppt.
3- Fehling's solution:
A neutral solution of formate reduces fehling's solution in presence of
Na2CO3.
Acetic Acid; ethanoic acid
CH3COOH
Mol. wt. 60, b.p 122.13ºC. Soluble in H 2O, alcohol, acetone, benzene,
volatile liquid. It has vinegar odor.
1- It does not contain CHO (c.f formic acid), so it does not reduce
permanganate, mercuric chloride, amm. AgNO3 or Fehling's solution.
2- Esterification: with ethanol it gives ethyl acetate (apple like odor).
3- FeCl3.
1 ml neutral FeCl3 was added to 2ml neutral acetic acid solution to give
blood red color, from ferric acetate (CH3COO)3Fe which by heating give
brown ppt. from basic ferric acetate CH3COOFe(OH)2.

Oxalic acid; Ethanedoic acid:

HOOC-COOH

Solid, M.W 90.4, sublime at 157°C, M.p. 101.5ºC hydrous, 182°C

anhydous, Soluble in H2O, and alcohol.
1- Reduction of acid KMnO4:
Warm gently a tube containing (0.5g of oxalic acid + 10ml H 2O). Add a

62
dilute solution of KMnO4 dropwise to obtain decolorization of the pink color.
2-CaCl2:
It gives Ca. oxalate (ppt.) on cold, which is insoluble in acetic acid but soluble
in dil HCl.
3- Conc. H2SO4 :
oxalic acid or oxalate with conc. H 2SO4 gives CO and CO2. No charring.
CO burns with blue flame.
Lactic acid
CH3-CH(OH)-COOH

Liquid, M.W 90.08. b.p. 103°C, miscible with H2O and alcohol. It has sour
milk odor.
1- Iodoform test:
Corresponding to CH3CHOH - group: Dissolve 0.1g of neutral lactate or
1ml of lactic acid in water (5ml). Add 2ml of NaOH (10%) solution followed by
addition of potassium iodide-iodine reagent. The latter reagent is added
dropwise with shaking until a persistent yellow color is obtained. Warm the test
tube in a water bath at 60°C if necessary.
The test is positive if a yellow ppt. of Iodoform is formed.
2- Conc. H2SO4:
Brisk effervescence takes place with evolution of CO, CO 2 and SO2.
The reaction mixture suffers blacking but no marked charring.
Tartaric acid; 2,3 dihydroxybutanedoic acid.

OH CH COOH
OH CH COOH

Solid, M.W. 150,09,M.p 171°C, soluble in water, alcohol, and acetone.

63
1- Fenton's test:
One drop of freshly prepared FeSO4 solution is added to a solution of
tartaric acid or its salt followed by 2 drops of H 2O2 solution and excess of
NaOH solution.
Violet coloration is produced due to the ferric salt of dihydroxy maleic acid.
HOOC C=C COOH
OH OH

2- CaCl2 As mentioned under formic acid.

Calcium tartarate is formed on cold and it is soluble in acetic acid.
3- Conc. H2SO4:
Tartaric acid or its salt gives with conc. H 2SO4 on heating charring,
effervescence and odor of burnt sugar.
Citric acid; 2-hydoxy-1,2,3- propane tricarboxylic acid.
CH2COOH
HO C COOH
CH2COOH

M.w, 192.14 M.p 53°C solid soluble in H2O, alcohol and ether.
1- Denige's test.
Dissolve citric acid or citrate salt (0.5g) in H2O (10ml) then add 1ml of acid
mercuric sulfate followed by a few drops of 2% KMnO 4 solution. Warm the
mixture from up to down. Decolorization occurs with the formation of a heavy
white ppt. immediately.
2- CaCl2 :white ppt after neutralization and boiling
Calcuim citrate is formed after boiling and it is insoluble in acetic acid.
3- Conc. H2SO4:
The solution turns yellow with evaluation of CO and CO 2 but no charring
takes place. The yellow color is due to the formation of acetone dicarboxylic
acid.

64
 Aromatic Acids

Phthalic acid; 1,2 - benzene dicarboxylic acid

M.W. 166.14, M.p 211°C (dec.), soluble in alcohol.

1- Dry heat: Aromatic
2- Soda-lime Benzene odor on hot.
3- Phthalein test:
Few crystals of phthalic acid and phenol are fused in dry test tube in
presence of few drops of conc H2SO4.
The reaction mixture, which contains phenolphthalein is poured into dil
NaOH solution to give red solution which is decolorized by acid.
4- Neutral FeCl3
Buff colored precipitate is formed. Addition of dilute acid to the precipitate
led to the formation of a white ppt of the aromatic acid, which you start with.
5- Fluorescein test:
Mixture of phthalic acid, resorcinol, and few drops of conc. H 2SO4 was
fused completely then pour the reaction mixture into 10ml NaOH to give red
coloration which exhibit an intense green fluorescence on further dilution with
water.
Benzoic acid: benzene carboxylic acid.

65
 Solid M.w:122.12, M.p 122.12°C,soluble in alcohol, ether, acetone, and
choroform.

1- Soda lime: as mentained under phthalic acid

2- Phthalien test: Does not responde to the test.

3- Fluorescien test: Does not responde to the test.

4- Neutral FeCl3: as mentained under phthalic acid.

Salicylic acid; 2- Hydroxy benzoic acid.

Solid, M.w. 138.12, M.p. 159°C soluble in alcohol, ether, acetone it is

considered as acid and/or phenol.

1- Soda lime: It gives phenol on hot.

2- FeCl3: It gives violet color without neutralization.
3- Phthalein test:
As mentioned under phthalic acid (bright red coloration).
4- Esterification:
With methyl alcohol it gives methyl salicylate (oil of winter green odor).
5- Formaldehyde test:
In a dry evaporating dish, moist few crystals of salicylic acid or its salt with
few drops of formalin. Add few drops of conc. H 2SO4 and notice the produced
crimson red color.

66
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

67
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

68
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

69
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

70
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

71
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

72
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

73
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

74
 Unknown No: Date / /

A-Physical Characters:
1-Condition:

2-Color:

3-Odor:

4-Solubility/ Miscibility

a-H2O
Litmus Paper: Comment:

Anhydrous CuSO4 Comment:

b-NaOH(10%): Comment:

c-NaHCO3 Comment:

d-Dil HCl: Comment:

e-Conc. H2SO4 Comment:

B) General Reactions:

1) Action of Soda lime:

On Cold:
On Hot: Comment:

2) Action of NaHCO3
Comment:

3) Action of FeCl3:
Comment:

4) Element Test X N S
( ) ( ) ( ) Comment:
5) Special Tests
1)

2)

75