CHEMISTRY DEPARTMENT

INTRODUCTION TO ORGANIC
CHEMISTRY
(CHEM-108) and (CHEM-109)
Student Name
Student ID

Written By
Ahmad Jumah Ibrahim Aldossari
Rayana Alkhalifah Razan Alotaibi

Reviewed By
Dr. Sultan Almadhhi Dr. Zainab Almarhoon

2024
 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Table: 109 CHEM EXPERIMENTS 1446 FIRST SEMESTER

DAY DATE EXPERIMENT NOTES

( 5/ 7 /1446 H )
SUNDAY REGISTRATION
( 5/ 1 /2025 G )

( 12/ 7 /1446 H ) EXP (0) INSTRUCTION, EQUIPMENT AND SAFETY

SUNDAY
( 12/ 1 /2025 G ) EXP (1) SOLUBILITY

( 19/ 7 /1446 H )
SUNDAY EXP (2) EXTRACTION
( 19/ 1 /2025 G )

( 26/ 7 /1446 H ) QUIZ (1)

SUNDAY EXP (3) ALIPHATIC HYDROCARBONES
( 26/ 1 /2025 G ) IN EXPERIMENT (1,2)

( 3/ 8 /1446 H )
SUNDAY EXP (4) AROMATIC HYDROCARBONES
( 2/ 2 /2025 G )

( 10/ 8 /1446 H )
SUNDAY EXP (5) HYDROXY COMPOUNDS
( 9/ 2 /2025 G )

( 17/ 8 /1446 H ) QUIZ (2)

SUNDAY EXP (6) ALDEHYDES AND KETONES
( 16/ 2 /2025 G ) IN EXPERIMENT (3,4,5)

( 25/ 8 /1446 H )
SUNDAY EXP (7) PREPARATION OF ASPIRIN
( 24/ 2 /2025 G )

( 3/ 9 /1446 H )
SUNDAY EXP (8) CARBOXYLIC ACIDS
( 3/ 3 /2025 G )

( 10/ 9 /1446 H )
SUNDAY VACATION
( 10/ 3 /2025 G )

( 8/ 10 /1446 H ) QUIZ (3)

SUNDAY EXP (9) CARBOHYDRATES
( 6/ 4 /2025 G ) IN EXPERIMENT (6,7,8)

( 15/ 10 /1446 H )
SUNDAY EXP (10) AMINO COMPOUNDS
( 13/ 4 /2025 G )

( 22/ 10 /1446 H )
SUNDAY FINAL EXAM
( 20/ 4 /2025 G )

( 29/ 10 /1446 H )
SUNDAY ALTERNATIVE EXAM
( 27/ 4 /2025 G )
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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

INTRODUCTION

Instruction, Equipment and Safety

PLEASE READ THE FOLLOWING BEFORE YOUR FIRST DAY IN THE LAB.

Aim and Purpose of the Course

Obviously the overall aim of the course is to give you experience in practical
organic chemistry and help you generally to learn about organic chemistry as a part
of medical/pharmacy course, but the purpose of the course will be clearer perhaps
from the following five objectives:
1) Experience the process of discovery for yourself and relate it to the role played
by experiment in scientific investigations.
2) Become familiar with isolating and purifying compounds by solvent/solvent
extraction.
3) Handle as wide a variety of compounds bearing different functional groups as
possible.
4) Exploit the opportunities for learning about organic chemistry during the
practical time to the full by asking your demonstrator questions.

Continuous Assessment and the Practical Exam

You will receive a mark for your laboratory work after each experiment. Credit
for an experiment will be based on attendance, and completion of the experiment to
your demonstrators’ satisfaction. He will be looking at a number of different things
such your neatness and tidiness while working in the laboratory. Your demonstrator
will grade your book like this:
A = Excellent result
B = Satisfactory
C = poor work

This grading will count towards your final grade and will help you to assess
how well you are progressing in your practice of organic chemistry. For this reason,
your demonstrator will discuss the assessment with you when he grades the
experiment at the end of the practical period.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Experimental Method and Write-up

No note books are required. Spaces are provided at appropriate places in the
manuals for you to record your observations, results etc. These must be written in
during the laboratory period and graded by your demonstrator before you leave.

General Instructions
This course deals with a number of test tube reactions which illustrate many of
the functional groups covered in the lecture course. These test tube experiments ae to be
done during the first half period that you are in the lab.
The first experiments involve important practical techniques. These experiments are
followed by experiments which follow the lecture course closely, so the lectures and
practical are all part of the same organic chemistry course.
When you first come into the laboratory you will be allocated a certain cupboard
containing most of the apparatus required for this terms work. Make sure all your
apparatus is returned to this cupboard at the end of every practical.
Additional supplies of more special apparatus is also available for common use, but
of limited supply. It is essential that this apparatus is returned clean at the end of each
practical.
Please refer to the lecture material before you come to the laboratory so that you are
familiar with the organic chemistry involved before you carry out any reaction.

Grading
Thirty percent of your final grade will come from the practical part of the course. At
the end of the course there will be a final practical exam. In addition, there will be five
or three “drop quizzes”, five of which will count towards your grade. These “drop
quizzes” will be short 5-minute test which will come without warning. They are
designed to encourage you to read the instructions concerning the experiment before
you come to the lab.
Distribution Marks
Attendance and Reports 10
Quizes 5
Final Exam 15
Total 100

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PRACTICAL ORGANIC CHEMISTRY CHEM 109

Laboratory Equipment

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

List of Glassware and Equipment

1) Condenser
2) Round-bottomed flask (50 mL and 100 mL) 3) Distilling head.
4) Adaptors.
5) Stoppers.
6) Separating funnels.
7) Beaker (50 mL, 100 mL, 250 mL and 400 mL).
8) Conical flask (100 mL and 250 mL).
9) Buchner funnel.
10) Buchner flask.
11) Funnel.
12) Glass rod.
13) Capillary tubes.
14) Test tubes.
15) Washing bottles.
16) Test tube rack.
17) Stand.
18) Clamps.
19) Test tube holder.
20) Heating Mantel 50 mL.
21) Watch glass.
22) Brush.

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PRACTICAL ORGANIC CHEMISTRY CHEM 109

‫قائمة بالمختصرات الكيميائية‬

Sol. Soluble ‫ذوبانية‬

Insol. Insoluble ‫غير ذائبة‬

Eff. Effervescence ‫فوران او تصاعد غاز‬

Ppt. Precipitate ‫راسب‬

Dil. Dilute solution ‫محلول مخفف‬

Conc. Concentrate solution ‫محلول مركز‬

Obs. Observation ‫المشاهدة‬

Res. Result ‫النتائج‬

mL Milliliter ‫ملليليتر‬

min Minutes ‫دقائق‬

m.p Melting point ‫درجة االنصهار‬

b.p Boiling point ‫درجة الغليان‬

g Gram ‫الجرام‬

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Safety

A chemistry lab can be dangerous place. If you work with care, however you
ought to survive and not eliminate your neighbors. Therefore: -

1) ALWAYS ware safety glasses in the lab. You may only be sitting at your bench
writing in your manual, but your neighbor’s distillation may explode.
2) NEVER, but never, allow ANY organic compound on your skin or breathe in
the dust from a solid or spray from a liquid.
Some compounds are labelled as particularly dangerous. Carcinogenic ones
cause cancer, some apparently harmless ones, like benzene, are very toxic
indeed.
ALL ARE LETHAL IN SUFFICIENT QUANTITY.
Rubber gloves are available to protect your hands.
3) NEVER boil organic compounds in the open lab or allow gases to escape, use
the fume cupboard.
4) BEWARE of FIRE. Know where the fire extinguishers are. Look around you
before lighting your burner. In particular, make sure no one is using ether or
petrol nearly.
5) HANDLE glass-ware CAREFULLY. Use quick fit apparatus, and watch for
chipped or cracked apparatus: return it to the preparation room.
6) REPORT all accidents to your demonstrator. You may think you are “all right”
but it is not worth taking chances.

Keeping your bench clean is most important, always clean up at all times. You will
have your grade reduced if you keep it in an untidy mess, the same applies to your
locker.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 1 Date:

Solubility

General Rule: Like dissolve like

Water is:
Polar
H-bond donor and acceptor
Solvates ions

Test-tube 1
- Place 1 mL of distilled water in the test tube.
- Add 0.5 ml of hexane (CH3CH2CH2CH2CH2CH3)
- Shake

Hexane is:
1) non-polar.
2) non- H- bonding.
3) does not solvate ions.

Test-tube 2
- Place 1 mL of distilled water in the test tube.
- Add 0.5 mL of ethanol (CH3CH2OH).

- Shake.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Test-tube 3
- Place 1 mL of distilled water in the test tube.
- Add 5 drops of 1-hexanol (CH3CH2CH2CH2CH2CH2OH)
- Shake.
In hexanol, the ratio of water insoluble “part” to water soluble “part” is high.
Test-tube 4
- Place 1 mL of distilled water in the test tube.
- Add 1 mL of diethylether (CH3CH2OCH2CH3).
- Shake.
- In the same tube add 1 drop of (KMnO4).
- Add 1 mL of ethanol.
- Shake well.

Test-tube 5
- Place 1 mL of distilled water in the test tube.
- Add 1 mL of chloroform (CHCl3).
- Shake.
Ether and chloroform are good solvents for extraction from aqueous solutions.
Test-tube 6
- Place 1 mL of chloroform in the test tube.
- Add 1 mL of water.
- Add 1 mL of methyl red solution (in water).
- Shake.
Therefore, the methyl red is preferentially soluble in …………………………..

- Add 3 drops of 5% NaOH solution to the methyl red/CHCl3/H2O mixture

and shake well.
HA = methyl red

HA + NaOH Na+A- + H2O

water

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report Number 1

Test Observation Result

H2O + Hexane

H2O + Ethanol

H2O + Hexanol

H2O + Ether

H2O + Ether + Ethanol

H2O + Chloroform

H2O + Chloroform + methyl red

5% NaOH solution to the mixture

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions:
1) Which of these organic solvents will form one layer with water:
a) Benzene.
b) Propanol.
c) Methanol.
d) Dipropylether.
e) Octanol.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 2 Date:

Extraction

It is evident from the test-tube reactions that a compound dissolved in one solvent can
be extracted into another solvent if:
a) It is more soluble in the second solvent; and
b) The two solvents are immiscible.
On a preparative scale these extractions are carried out in a “separating funnel”,
which is constructed to allow easy separation of two immiscible solutions.

Figure 1: Diagram of separating funnel apparatus.

The objective of this experiment is to make you familiar with this technique.

Table 1: List of common solvents that can be used for extraction from water.

Solvent Formula
Hexane (light petrol) C6H14
Benzene C6H6
Diethyl ether (ether) (C2H5)2O
Ethyl acetate CH3COOC2H5
Chloroform CHCl3
Carbon tetrachloride CCl4
NOTE that methanol, ethanol, and acetone are miscible with water and cannot be used
for extraction from water.
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PRACTICAL ORGANIC CHEMISTRY CHEM 109

Separation of Mixture of Basic and Acidic Compounds

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Caution (Before you start)

o Since most organic chemicals are hazardous in some way (e.g. inflammable,
poisonous vapor or poisoning through skin) take care not to get any on your hand.
o The m-nitroaniline is highly colored and toxic so you will be able to observe any
contamination. o If you get any, on your skin wash your skin with soap and water.
Do not wash with an organic solvent, this would assist passage of the contaminant
through your skin.
Procedure
- In a 50 mL conical flask weigh approximately 2 g of a mixture of benzoic acid
(C6H5COOH), HA and m-nitroaniline.
- Add 25 mL of chloroform.
- Transfer the solution to a 50 mL separating funnel, using a funnel (Figure 1).

Solvent Extraction General Procedure

- Clamp the separatory funnel securely with the tap lubricated with Vaseline and
closed.
- Pour in the chloroform solution through a funnel and use in a little extra chloroform
to wash in the last traces of a powder sticking to the walls of the flask and to the
funnel.
- Add 20 mL of 10% sodium hydroxide solution to the separatory funnel through the
funnel.
- Insert the stopper (lubricated with Vaseline) and shake the separating funnel to mix
the layers thoroughly, releasing the pressure via the top at frequently intervals.
- Allow the layers to separate.
- Remove the stopper. Run off the lower layer into a 50 mL conical flask; not to fast
or you will create a vortex. Close the tap when the bore of the tap contains the last
of the lower layer.
The chloroform layer contains …………………………………………………
The aqueous layer contains …………………………………………………….
- Run the upper (aqueous) layer into a 100 mL conical flask.
- Add to upper layer conc. HCl until no whiter precipitate forms. It may be necessary
to cool the solution. The precipitate is ………………………………….............

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Allow the solution to cool and then suction filter off the solid, wash it with a little cold
water and dry in an oven. Suction Filtration
Apparatus: Buchner funnel, flasks and filter paper (Figure 2).
1) Choose the correct size of filter paper, wet it all over with water and place it centrally
in the funnel.
2) Briefly apply suction to secure the paper firmly in place.
3) Pour in the slurry of crystals. Do not fill to more than 2/3.
4) Use filtrate (mother-liquor) to wash in any crystals which remains stuck to the walls
of the flask.
5) To wash the crystals with cold water, first release the vacuum slurry the crystals
taking care not to damage the filter paper then reapply the suction.
To dry, place the crystals on a clean filter paper, and cover with another piece of filter
paper.

Figure 2: Buchner funnel.

Then put chloroform layer back into separating funnel.

Extract with 20 mL of 10% HCl solution.

The chloroform layer contains………………………………………….

The aqueous layer contains……………………..……………………..

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Separate the layers.

Keep the upper aqueous layer and put the lower chloroform layer into the residue bottle.
To the aqueous layer, add 10% NaOH until no further precipitation takes place.
The precipitate is …………………………….……………………….
Suction filter the solid, wash with a little water and dry in the air at room temperature.
Submit your sample to your demonstrator before you leave.

Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions
Predict the outcome of the following extractions?
1) Benzoic acid dissolved in ether:
A) Extract with aqueous HCl.
B) Extract with H2O.
C) Extract with aqueous NaOH.

2) Aniline dissolved in ether:

A) Extract with aqueous HCl.
B) Extract with H2O.
C) Extract with aqueous NaOH

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 3 Date:

Aliphatic Hydrocarbon (Bonding) (Alkanes and Alkenes)

Alkanes
In general C – H and C – C bonds in alkanes are unreactive towards polar
reagents. Reaction generally occurs by the formation of radicals in the presence of a
suitable initiator (Z.). This type of reaction is called Free Radical Substitution.

Bromine to an Alkane:

Test-tube 1
- Take 1 mL of cyclohexane.
- Add 3 drops of Br2/CCl4 solution.
- In the presence of light from the sun or a UV lamp, the bromine undergoes
hemolytic fission and readily reacts with the cyclohexane.

Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

- Dip a clean glass rod into conc. NH4OH and hold the glass rod over the mouth of the
test tube. What happened?
……………………………...…………………………………………………
………………………………………………………………………………...
The observing is the formation of NH4Br which is a test for the presence of HBr.

Chemical equation:

Alkenes
Alkenes undergo polar addition reactions initiated by electron rich system of
the double bond.

Addition of Bromine to an Alkene

Test-tube 2
- Take 3 drops of cyclohexene.
- Add 3 drops of Br2/CCl4 solution.
Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Alkene with Potassium Permanganate (KMnO4)

Reaction with dil. KMnO4 solution is also a test for the presence of carbon- carbon
double bonds. The double bond of an alkene is easily oxidized to a di-OL.

Test-tube 3
- Take 3 mL of dil. KMnO4 solution.
- Add 3 drops of cyclohexene.
- Shake.

Chemical equation:

OH
KMnO4

OH

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PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report Number 2
Test Observation Result Chemical equation
 PRACTICAL ORGANIC CHEMISTRY CHEM 109
Questions:
Complete the following reactions:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 4 Date:

Aromatic Hydrocarbons

Benzene

Aromatic compounds have multiple double bonds; these compounds do not undergo
addition reactions. Their lack of reactivity toward addition reactions is due to the great
stability of the ring systems that result from resonance.

Bromine with Benzene

Test-tube 1
- Take 1 mL of 90% acetic acid (solvent).
- Add 5 drops of benzene.
- Add 5 drops of Br2/CCl4.
- Pour the contents of the tube into the vial containing the iron powder, shake.
Polarization of the bromine occurs

Br Br Fe Br

The positive bromine species is a better electrophile than molecular bromine.

The type of reaction in benzene is electrophilic aromatic substitution.

Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Benzene with Potassium Permanganate (KMnO4)

Test-tube 2
- Take 1 mL of dilute aqueous KMnO4 solution.
- Add 2 drops of benzene. - Shake.
Chemical equation:

+ KMnO4 NO REACTION

Oxidation of Alkyl Side-Chains

alkylbenzenes are oxidized to benzoic acids (-COOH), as long as the alkyl group
contains at least one hydrogen at the benzylic position.

p-Methoxytoulene with KMnO4

p-Methoxytoulene

Test-tube 3
- Take 1 mL of dilute aqueous KMnO4 solution.
- Add one drop of p-methoxytoulene.
- Shake.
Chemical equation

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Anisole (Methoxybenzene) with KMnO4

Methoxybenzene

Test-tube 4
- Take 1 mL of dilute aqueous KMnO4 solution.
- Add 2 drops of anisole (methoxybenzene).
- Shake.

Nitration of Benzene
Nitration occurs when one (or more) of the hydrogen atoms on the benzene ring
is replaced by a nitro group, NO2. Nitrating mixture is concentrated nitric acid
(HNO3) with sulfuric acid (H2SO4).

Test-tube 5
- Take 1 mL of nitrating mixture (conc. H2SO4 + conc. HNO3).
- Add 5 drops of benzene.
- Shake well.
- Take about 20 mL of distilled water in a small beaker.
- Pour reaction mixture into this water.

Observation
NO2 NO2

NO2 NO2

NO2
Benzene Nitrobenzene 1,3- Dinitrobenzene
a liquid less a liquid more solid
dense than water dense than water

The main product of my reaction is ……………………………………………..

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report number 3
Test Observation Result Chemical equation
 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 5 Date:

Hydroxy Compounds (Alcohols and Phenols)

Preparation of Alkyl Halide from Alcohol

In practice:
Reaction 1

Thionyl choride
Reaction 2

pentachlorphosphors

Lucas' reagent
Test-tube 1
- Take 1 mL of conc. HCl in three test tubes.
- Add 10 drops of t-butanol in test tube 1.
- Add 10 drops of isopropanol in test tube 2.
- Add 10 drops of ethanol in test tube 3.
- Shake.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Oxidation of Alcohols
Reaction with an oxidizing agent e.g. KMnO4, H2CrO4, is an important synthesis
of aldehydes, ketones and carboxylic acids.

- Take 1 mL of chromic acid (H2CrO4).

- Add 5 drops of ethanol (primary alcohol). - Place the tube in hot
water bath.

Chemical equation:

Test-tube 3
- Take 1 mL of chromic acid (H2CrO4).
- Add 5 drops of t-butanol (tertiary alcohol).
- Place the tube in hot water bath.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Phenols
Phenols are compounds that possess a hydroxyl group directly attached to an aromatic
ring.

Phenol

Ferric chloride (FeCl3)

phenol group will form a blue, violet, purple, green, or red -brown color upon
addition of aqueous ferric chloride (FeCl3). This reaction can be used as a test for phenol
group.

Test-tube 4
- Take 3 drops of the aqueous phenol solution. -
Add 2 drops of FeCl3 solution.

Chemical equation:

Acidity of Phenols
Resonance stabilization of the charge in the anion is responsible for phenols being
weak acids.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Test-tube 5
- Take 1 mL of aqueous phenol solution.
- Add 1 drop of bromothymol blue.
(pH color change of bromothymol blue; (yellow at pH 6.2) to (blue at pH 7.6).

Observation
The color of the solution …………………..………………………………………….
The solution has a pH of …………………..……………………………….………….

Test-tube 6
- Take 1 mL of aqueous phenol solution.
- Add 1 drop of bromophenol blue.
(pH color change of bromophenol blue; (yellow; pH 3.0 to blue; pH 4.6).

Observation
The color of the solution …………………….………..………………………….
The solution has a pH of ……………………………..…………………………...
Conclusion
The phenol solution therefore has a pH somewhere between ………. and ………
Electrophilic Substitution in Phenol
OH OH
Br Br
+ 3 Br2/H2O

Br
2,4,6-tribromophenol (white ppt )

Test-tube 7
- Take 3 drops of the aqueous phenol solution.
- Add 2 mL of bromine water.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report number 4
Test Observation Result Chemical equation
 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 6 Date:

Aldehydes and Ketones

O O
C C
R H R R
Aldehyde Ketone

Aldehydes and ketones are characterized by carbonyl group-polarized double bond.

C O

Attack by nucleophiles therefore occurs at the C+ end.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109
Carbonyl Compounds with Amines
Aldehydes and ketones could react with ammonia or 1º-amines to form imine
derivatives, also known as Schiff bases (compounds having a C=N function).

Test-tube 1
- Take 0.5 mL of ethanol.
- Add 5 drops of benzaldehyde.
- Add 1 mL of p-methoxyaniline (p-Anisidine) in ethanol-water.
- Shake.
- Place in a hot water bath.
- Cool the tube and add 1 drop of water.
Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109
2,4-Dinitrophenylhydrazone Formation

The reaction is used to identify aldehydes and ketones.

Test-tube 2
- Take 1 mL of 2,4-dinitrophenylhydrazone (2,4D.N.P.) reagent.
- Add 1 drop of acetaldehyde or acetone.

Oxidation of Carbonyl group

Aldehydes could oxidize to form carboxylic acid while ketone does not oxidize.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Test-tube 4
- Take two test tubes add 5 drops of acetaldehyde and the other add 5
drops acetone.
- Add 10 drops of chromic acid for the two test tubes (take care). - Place
the tubes in the hot water bath. Chemical equation:

Reduction of Carbonyl group

Addition of a hydride anion (H:-) to an aldehyde or ketone gives an alkoxide
anion, which on protonation yields the corresponding alcohol. Aldehydes
produce 1º-alcohols and ketones produce 2º-alcohols.

Test-tube 3
- Take 1 mL of ethanol.
- Add 5 drops of benzaldehyde.
- Add 2 mL of NaBH4 solution.
- Allow to stand.
- Add a few pieces of ice to a small beaker. - Pour into the reaction mixture.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Chemical equation:

Distinguishing Test between Aldehyde and Ketone

Tollen’s reagent (a weak oxidizing agent) – ammonical silver nitrate with NH 4+ as the
oxidant.

Test-tube 5
-Take 2 mL of AgNO3 solution.
-Add 8 drops of 5% NaOH solution.
-Add ammonium hydroxide dropwise and with mixing until the black precipitate
just dissolves. (This is Tollen’s reagent) - Divide the solution into 2-test-tubes.
Reaction E (i)
-Add 1 drop acetaldehyde of to the sample of Tollen’s reagent in the test-tube.
-Place the tube in the hot water bath.

Chemical equation:

Reaction E (ii)
- Add 1 drop of acetone to the sample of Tollen’s reagent in the test-tube.
- Place the tube in the hot water bath.

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PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report number 5
Test Observation Result Chemical equation
 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 7 Date:

Preparation of Aspirin

Salicylic acid and many of its derivatives are antipyretics and analgesics but
the acetyl derivative is not having any bad side-effects. Willow bark tea, which
contains salicylic acid, was known to Hippocrates as a valuable analgesic (“Salicylic
acid” is derived from the latin salix, willow).
Acetylsalicylic acid was first prepared in 1854 by a German called Gerhardt,
but it was not until forty years later that its medicinal value was recognized when
Hoffmann, a German chemist, tried it on his father and found that it eased the old
man’s rheumatic pains.
Aspirin is therefore one of the earliest examples of the alternation in
chemotherapeutic properties that can result from a seemingly minor alteration in
molecular structure. Of course, aspirin itself can cause undesirable side effects in
some people (gastric irritation and skin rashes) but these effects are not nearly
(headache, dizziness, mental confusion, nausea, etc.).
According to one textbook “over 27 million pounds of aspirin are consumed
yearly in the United States (sufficient to treat over 17 billion headaches)”. Thus
though aspirin is widely used its mechanisms of action are still unknown. Both the
antipyretic and the analgesic effects for many years thought to be central; that is, its
drug somehow affects the temperature control center (the hypothalamus) and the pain
center (subcortical regions, probably the thalamus) of the brain. More recently a new
hypothesis of action has been advanced. The drug may act locally to reduce fever,
pain and inflammation by inhibiting cellular release of a chemical which mediates
these defense reaction, in particular the secondary defense mechanism (its substances
including histamine, kinins and prostoglandines).

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Procedure
- Weigh out 5 g of salicylic acid.
- Place the salicylic acid in a 125 mL conical flask. - Add 10 mL of acetic
anhydride in the hood.
- Add 1-2 mL of conc. H2SO4.
- Stopper flask with plug of cotton wool.
- Swirl the reaction mixture for 10 minutes.
- After 10 minutes, add 25 mL of ice water and swirl for 10 minutes.
- Collect the precipitate in a small Buchner funnel.
- Wash it with 10 mL of ice water.
- Dry the product in the air.
- Weigh and determine the melting point.

Ferric Chloride (FeCl3)

Ferric chloride forms complexes with enols and phenol. These complexes are
usually dark in color, dark purple and dark green being common. These colored
complexes form the basis of a test for phenols.

Procedure
- Place 2 mL of ferric chloride solution in the test-tube (Ferric chloride solution
has a pale yellow color).
- Add to it a few crystals of salicylic acid.
Repeat the test but instead of using salicylic acid, add a few crystals of your product.

Observation
………………………………………………………………………………………
…

Weight of Aspirin obtained = ……….. g.

Meting point of Aspirin = ............... C.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions:
Q1) What is the structure of Aspirin?

Q2) Write the chemical equation for preparation of Aspirin?

Q3) Why does FeCl3 react with Salicylic acid but does not react with Aspirin?

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 8 Date:

Carboxylic acids and Their Derivatives

Reaction of Carboxylic acid with Sodium bicarbonate

Carboxylic acids are stronger acids than phenols.

Test-tube 1
- Take 1 mL of 4% sodium bicarbonate solution (NaHCO3). -
Add one drop of 90% acetic acid solution.
Note the CO2 evolved (effervescence).

Chemical equation:

Relative Acidities of Some Substituted Benzoic Acid

a) Electron withdrawing substituents in Ar will reduce the charge on the

carboxylate anions.
b) The anion will therefore be stabilized.
c) The acid will therefore show a greater tendency to dissociate.
d) The acid will therefore be stronger if Ar is electron withdrawing than if Ar is
electron donating.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Test-tube 2, 3, 4
- Place 1 mL of p-nitrobenzoic acid in test-tube 2.
- Place 1 mL of benzoic acid in test-tube 3.
- Place 1 mL of p-methoxybenzoic acid in test-tube 4.
- Add 1 drop of bromophenol blue solution to each tube.
(pH color change of bromophenol blue; yellow (pH 3.0), blue (pH 4.6).
- Add 1 drop of 0.1M NaOH to each tube.

Observation
1) Color of p-nitrobenzoic acid …………………………………………
2) Color of benzoic acid …………………………………………………
3) Color of p-methoxybenzoic acid ……………………………………
Order of acidity:
…………………………………………………………………………………

Esterification

Test-tube 5
- Take 2 mL of the solution of sulfuric acid in methanol.
- Add 5 drops of the solution of salicylic acid in methanol.
- Place the tube in hot water bath.Take about 15 mL of cold water in a small beaker.
- Add the contents of the tube to the beaker.
The ester, methyl salicylate (oil of wintergreen) has a distinctive smell.
Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Amide Hydrolysis
Susceptible to basic (and acidic) hydrolysis but are less reactive than esters.

Test-tube 6
- Take 1 mL of the ethanol solution of acetamide.
- Add 1 mL of 10% NaOH solution.
- Then take red litmus and keep it on the top of the tube. - Place the tube in the
hot water bath.
Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report number 6
Test Observation Result Chemical equation

Esterification
 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 9 Date:
Carbohydrates

Carbohydrates are compounds containing C, H, O and the H and O are present

in the same proportion as in water. The word carbohydrate can be expressed as
hydrates of carbon because molecular formulas of these compounds.
Example; Glucose has the molecular formula C6H12O6, which might be written as
C6(H2O)6.
The chemistry of carbohydrates is mainly the combined chemistry of two
functional groups: the hydroxyl group and the carbonyl group.
Carbohydrates are usually classified according to their structure as;
1) Monosaccharides: (glucose, galactose and fructose).
2) Disaccharides: (sucrose, maltose and lactose). 3)
Polysaccharides: (starch and inulin).
The three classes of carbohydrates are related to each other through hydrolysis.

Monosaccharides (or simple sugars, as they are sometimes called) are

carbohydrates that cannot be hydrolyzed to simpler compounds.
Polysaccharides contain many monosaccharide units—sometimes hundreds or
even thousands. Usually, but not always, the units are identical. Example; starch and
cellulose, contain linked units of the same monosaccharide, glucose.
Oligosaccharides (from the Greek oligos, few) contain at least two and
generally no more than a few linked monosaccharide units. They may be called
disaccharides, trisaccharides, and so on, depending on the number of units, which may
be the same or different. Example; Maltose is a disaccharide made of two glucose
units. Sucrose is made of two different monosaccharide units: glucose and fructose.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Physical properties
Colorless solids, which decomposes on heating and therefore have no definite
melting points. All are soluble in cold water except starch.

General Reactions:
 Molisch's Test

Test-tube 1
- Take concentrated solution of the carbohydrate in water.
- Add equal amount of α-naphthol solution.
- Carefully add excess amount of concentrated H2SO4 inside the wall of the tube
to form a heavy layer at the bottom.
Observation
A deep violet ring is produced at the interface.
Shake the solution.

Observation
The violet color spreads through the whole solution.

 Reduction of Fehling's Solution (A+B)

Test-tube 2
- Take 1 mL of sugar solution.
- Add 1 mL of Fehling's solution (A+B). - Boil the soln. for
one minute.
Observation
- Glucose, Fructose, Maltose (Malt sugar), and Lactose (Milk sugar); Reduction
takes place and a red ppt. of cuprous oxide is formed.
- Starch and Sucrose give –ve result.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

 Barfoed′s Test: (Copper Acetate in Acetic Acid Solution)

Test-tube 3
- Take 1 mL of sugar solution.
- Add 1 mL of Barfoed's reagent. - Boil the soln. for one
minute.
Observation
- Glucose and Fructose give red ppt. of cuprous oxide appears.
- Maltose gives red ppt. only after prolonged heating (more than 15 min) as it is
hydrolyzed to glucose.
- Lactose (Milk sugar) gives red ppt. only after prolonged heating (more than 15
min) as it is hydrolyzed to glucose and galactose.
- Starch and Sucrose give –ve result.

 Rapid Furfural Test

Test-tube 4
- Take 1 mL of dil. sugar solution.
- Add 1 mL of α-naphthol solution.
- Add 3 mL of conc. HCl. - Boil in a water bath.
Observation
- Glucose, Maltose, and Lactose (Milk sugar); a violet color appears after some
time.
- Fructose and Sucrose (Can sugar); an immediate violet coloration on boiling.
 Iodine Test (I2 Solution)

Test-tube 5
- In two test tubes take 1 mL of dil. Sugar (Sucrose and Starch) solution.
- Add 1 mL of I2 solution.
Observation
- Starch gives blue-black color
- Sucrose –ve

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109
 Tollen’s reagent (Ammoniacal Silver Nitrate)
Test-tube 6
- Take 1 mL of sugar solution.
- Add 1 mL of dil. ammoniacal silver nitrate (Tollen’s reagent).
- Boil the soln. for one minute.
- Place the test tube on a water bath.
Observation
- Glucose, Fructose, Maltose (Malt sugar) and Lactose (Milk sugar); a silver mirror
is produced in 1-2 minutes.
Starch and Sucrose (Can sugar) give –ve result.

 Osazone formation
Test-tube 7
- Take solid sugar, phenyhydrazine hydrochloride, and sodium acetate in the ratio
of 1:2:3.
- Add 5 drops of water.
- Place in a hot water bath for 10-15 minutes.
Observation
- Glucose and Fructose; yellow ppt. of the osazone appears after 10-15 minutes.
Examine under the microscope, yellow needles aggregated in the form of
sheaves.
- Maltose (Malt sugar); Forms yellow ppt. of osazone soluble in hot water, the
yellow crystals of the osazone will appears only after cooling the soln.
Examine the crystals under the microscope.
- Lactose (Milk sugar); Forms yellow ppt. of osazone soluble in hot water, the
yellow crystals of the osazone will appears only after cooling the soln.
Examine the crystals under the microscope.
- Starch and Sucrose (Can sugar); –ve result.

Glucosazone Maltosazone Lactosazone or Fructosazon

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

 Water Solubility Test

Test-tube 8
- Take solid sugar.
- Add water. - Shake.
Observation
- Mono-and disaccharides are soluble in water.
- Starch insoluble in water.

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PRACTICAL ORGANIC CHEMISTRY CHEM 109
General Scheme for Identification of Carbohydrates
Starch, Sucrose, Glucose, Fructose, Maltose, Lactose

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report number 7 Sugar name:

Test Observation Result Chemical equation

Molisch's Test

Fehling's Solution
(A+B)

Barfoed's Test

Rapid Furfural Test

Iodine test

Tollen’s reagent

H2O
 PRACTICAL ORGANIC CHEMISTRY CHEM 109

EXPERIMENT 10 Date:

Amino Compounds

Basicity of Amines

Test-tube 1
- Take 1 mL of aqueous aniline.
- Add 2 drops of phenolphthalein.
(pH color change of phenolphthalein; colorless pH 8.0 to pink pH 10.0).
Observation

Aniline: Color …………………. pH is ……………….…

- Add 2 drops of p-nitrophenol solution to the aniline tube.
(pH color change of p-nitrophenol; colorless pH 5.0 to yellow pH 7.0.)
Observation

Aniline: Color …………………. pH is …………………

Test-tube 2
- Take 1 mL of aqueous methylamine.
- Add 2 drops of phenolphthalein.
(pH color change of phenolphthalein; colorless pH 8.0 to pink pH 10.0).
Observation

Methylamine: Color ………………. pH is ……………

The pH of the aniline solution is between …………… and ……………..…
Aniline is ( less - more ) basic than methylamine.

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

The lone pair of electrons on the nitrogen of aniline is delocalized over the ring.

NH2 NH 2 NH 2 NH 2

Protonation of this nitrogen is therefore less favorable than in the case of methylamine
(no resonance possible).
Diazotization (Reaction with Nitrous Acid)

Test-tube 3
- Take 1 mL of the solution of aniline in 10% H2SO4.
- Slowly add 5 drops of NaNO2 solution.
- Shake the tube after adding each drop.
- Set the tube aside.

Chemical equation:

Test-tube 4
- Take 1 mL of 2-naphthol solution in sodium hydroxide.
- Pour a little (less than half) of the diazonium salt solution in Test-tube 4 into the
2-naphthol solution.

Chemical equation:

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 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Test-tube 5
- Take 10 mL of hot water.
- Add rest of the diazonium salt solution from Test-tube 4.
- Heat and swirl.

Chemical equation:

Bromination of Aniline
Aniline is highly reactive to electrophilic substitution reactions (-NH2 is a
strong electron-donor).

Test-tube 6
- Take 3 drops of aqueous aniline solution.
- Add 1 mL of bromine water.

Chemical equation:

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PRACTICAL ORGANIC CHEMISTRY CHEM 109

Report number 8
Test Observation Result Chemical equation
 PRACTICAL ORGANIC CHEMISTRY CHEM 109

Questions: