Experiment No.

Date:

PREPERATION OF BENZALDEHYDE PHENYL HYDRAZONE FROM

PHENYL HYDRAZINE

AIM

To prepare and submit benzaldehyde phenyl hydrazone form phenyl

hydrazine

REQUIREMENTS

Apparatus: Beaker, Iodine flask, funnel.

Chemicals: Benzaldehyde, phenyl hydrazine, glacial acetic acid.

PRINCIPLE

Phenyl hydrazine condenses readily with aldehydes and ketones to give

phenyl hydrazones which are usually a crystalline compound of sharp melting
point. Therefore they are used to identify the aldehydes and ketones from which
they have been formed. Phenyl hydrazine is usually dissolved in acetic acid for
hydrazone formation.

PROCEDURE

Dissolved 3ml of glacial acetic acid in 20ml of water taken in an iodine flask
and added 4ml phenyl hydrazine and then added 2ml benzaldehyde. Corked the
flask and shake the contents vigorously. Allowed to stand for 15 minutes with
occasional shaking. Filtered the product. Washed with very dilute acetic acid and
then with water and dried. Recrystallised from rectified spirit.
USE

To identify aldehydes and ketones.

REPORT

Benzaldehyde phenyl hydrazone was prepared from benzaldehyde phenyl

hydrazine and submitted.

The percentage yield of benzaldehyde phenyl hydrazone prepared was found

to be..............................

REFERENCE

Practical oraganic chemistry, IV edition; F G Mann and B C Saunders; Pag

e no.: 229.
Experiment No.2

Date:

PREPERATION OF BENZANILIDE FROM BENZOYL CHLORIDE

AIM

To prepare and submit benzanilide from benzoyl chloride.

REQUIREMENTS

Apparatus: Beaker, Iodine flask, funnel.

Chemicals: Aniline, Benzoyl chloride, 10% Sodium Hydroxide, Ethanol.

PRINCIPLE

Benzanilide is prepared by Schotten Baumann Method of Benzoylation. The

reaction involved in the synthesis is the benzoylation reaction. The substitution or
the replacement of one or more hydrogen atoms in an orgainc compound by one or
more benzoyl groups is known as benzoylation. Benazanilide is prepared by the
recation between a primary amine, aniline and a bezoylating agent, benzoyl
chloride in 10% NaOH solution. The reaction mixture should be alkaline
throughout the experiment. Sodium hydroxide neutralizes the hydrochloric acid
formed during the raction and also hydrolyzes excess of unreacted benzoyl
chloride. Since, acetic anhydride and acetyl chloride are readily hydrolyzed by
water, acetylation is carried out in the avsence of water, while benzoylation may be
achieved in aqueous solution.
PROCEDURE

2.5ml of aniline and 25ml of 10% aqueous sodium hydroxide was placed in
a 250ml stoppered iodine flask. To this 3.5ml of benzoyl chloride was added, the
flask was stoppered immediatey and shaken vigorously for 10 minutes. Heat was
evolved in this reaction. The crude benzoylated derivative was separated as a white
powder. Whent the reaction was completed (i.e when the odour of benzoyl chloride
can no longer be detected; smell cautiously), made sure that the reaction mixture
was alkaline and was diluted with 10ml of water. Filtered the product, wahed with
water nad drained. Recrystallised from alcohol.

USE

It is used as an anti- atherosclerotic agent.

It is used in the manufacture of dyes and perfumes.

REPORT

Benzanilide was prepared from benzoyl chloride and submitted.

The percentage yield of benzanilide prepared was found to be...................

REFERENCE

Elementary Practical oraganic chemistry, Part I, Small Scale Preperations,

Arthur Vogel; Page no.: 270.
Experiment No.3

Date:

PREPERATION OF PHENYL BENZOATE FROM BENZOYL

CHLORIDE

AIM

To prepare and submit phenyl benzoate from benzoyl chloride.

REQUIREMENTS

Apparatus: Beaker, iodine flask, filtration pump.

Chemicals: Sodium hydroxide, benzoyl chloride, phenol.

PRINCIPLE

This synthesis is based on Schotten Bauman reaction. Benzoytlation reaction

when carried out in the alkaline medium is known as Schotten Bauman reaction.
This reaction ia an example for benzoylation, esterification as well as nucleophilic
substitution reaction. Phenol reacts with benzoyl chloride in the presence of
sodium hydroxide to form phenyl benzoate as main product and hydrochloric acid
as the side product. The benzoates of few phenols are liquids. Many phenols do
however yield crystalline benzoyl derivatives. These are useful for charcetirisation.
In this method of benzoylation phenols react with benzoyl chloride in the presence
of aqueous NaOH. The reaction is usually carried out in dilute alkali. Esterification
of phenol with benzoyl chloride yields phenyl benzoate. Active hydrogen of
amines and phenols can be substituted by benzoyl group. This is known as
benzoylation reaction.
PROCEDURE

2.5ml phenol was dissolved in 38ml 10% aqueous sodium hydroxide

solution in an iodine flask. 4.5ml benzoyl cloride was added and the flask was
corked and the reaction mixture was shaken vigorously for 10 minutes. The
precipitate of benzoate was filtered off and washed with water and then dried.

USE

Treatment agianst lice and scabies.

Excepient in some testosterone replacement medium for treating

hypogonadism.

Preperation of lotion.

Insect repellent.

REPORT

Phenyl benzoate was prepared from benzoyl chloride and submitted.

The percentage yield of phenyl benzoate prepared was found to

be...................

REFERENCE

Experimental Pharmaceutical Organic Chmenistry; K S Jain; Page No: 172.

Experiment No.4

Date:

PREPERATION OF PARA BROMO ACETANILIDE FROM

ACETANILIDE

AIM

To prepare and submit para bromo acetanilide from acetanilide.

REQUIREMENTS

Apparatus: Beaker, funnel, conical flask, glass rod.

Chemicals: Acetanilide, acetic acid, bromine and water.

PRINCIPLE

Acetanilide undergoes bromination with formation of mixture of ortho and

para bomo acetnilide. Ortho compound is formed in small amounts when
compared to para product and be readily eliminated by recrystallization. Bromine
upon dissociation will give bromonium ion and bromide ion. The acetamido group
is act as an activating and ortho para directing group. Due to bulky nature of
acetamido group instead at ortho position, electrophile attcks more at para position.

PROCEDURE

Dissolved 5g of acetanilide in 17ml glacial acetic acid taken in conical flask.

Kept it on ice bath and then added 12.1ml of bromine solution slowly to acetnilide
solution. Shaked the beaker throughout the addition to ensure thorough mixing.
After the complete addition removed flask from water bath. Allowed the flask to
stand at room temperature for 30 minutes. Shaked the flask occasionaly during this
period. Pour the solution into beaker containing crushed ice and added the mixture
in 250ml water with constant stirring. Filtered the solid, washed thoroughly with
water and recrystallized from alcohol.

USE

It is used as antipyretic and analgesic.

Synthesis of organic compounds.

REPORT

Para- bromo acetanilide was prepared from acetanilide and submitted.

The percentage yield of acetanilide prepared was found to be...................

REFERENCE

Practical Organic and Medicinal Chmeistry; Dr. Ramesh K Goyal; Page No:
64.
Experiment No.5

Date:

PREPERATION OF IODOFORM FROM ACETONE

AIM

To prepare and submit iodoform from acetone

REQUIREMENTS

Apparatus: Beaker, funnel, conical flask, measuring jar, water bath.

Chemicals: Acetone, potassium iodide, sodium hydroxide.

PRINCIPLE

It is based on the fact that when a carbonyl compound - hydrogen is treated

with a halogen in basic solution substitution of hydrogen occurs in - position.
When the ketone containing methyl group is treated with iodine solution in basic
medium, iodoform a yellow solid separates out. Iodoform test is given by methyl
ketones and acetaldehyde. Iodoform reaction can be used to distinguish methyl
ketone from other ketones.

PROCEDURE

Taken 0.6ml of acetone, , 6ml water and 3ml NaOH solution(10%) in a

conical flask. To this mixture added iodine solution (2g of iodine dissolved in a
solution of 3g potassium iodide in 100ml of water) dropwise till the colour of
iodine persist. Added few drops of 10% NaOH solution till the yellow colour
reappears. Filtered and recystallized from aqueous methanol.
USE

Used as disinfectant.

Used as antiseptic.

REPORT

Iodoform was prepared from acetone and submitted.

The percentage yield of iodoform prepared was found to be...................

REFERENCE

Experimental Pharmaceutical Organic Chemistry; K S Jain

Experiment No.6

Date:

PREPERATION OF p- NITROACETANILIDE FROM ACETANILIDE

AIM

To prepare and submit p- nitroacetanilide from acetanilide

REQUIREMENTS

Apparatus: Beaker, conical flask, filtration pump.

Chemicals: Acetanilide, glacial acetic acid, nitric acid, sulphuric acid.

PRINCIPLE

The preperation of p- nitroacetanilide from acetanilide is an example for

aromatic electrophilic substitution reaction. The acetamido group is a ring activator
and ortho- para director but less active than free amino group. Hence the para
position is most stable than ortho position and the substitution occurs at para
position. Hence acetanilide undergoes ready nitration to give p- nitro acetanilide.

PROCEDURE

Added slowly in small amounts with stiriing 5grams of finely powdered

acetanilide to 5ml glacual acetic acid contained in a beaker surrounded by ice. The
temperature of the nitric acid should not be allowed to rise above 50C. Then added
10ml of sulphuric acid. When the substance has dissolved completely, added 2ml
concentrated nitric acid drop by drop ahile stiriing the reaction mixture. Then the
reaction mixture is allowed to stand at room temperature with occasional stirring
for 30 minutes. Then poured the contents on to crushed ice and stirred vigorously
when crude p- nitroacetanilide is precipitated. Kept aside for 20 minutes and
washed the precipitate three or four times with cold water and then recrystallized
from boiling alcohol.

USE

As an intermediate in the production of paracetamol

Dyeing industry

REPORT

p-nitroacetnilide was prepared from acetanilide and submitted.

The percentage yield of p-nitro acetanilide prepared was found to

be...................

REFERENCE

Dr G Devala Rao Practical Medicinal Chemistry; Page No.: 16.

Experiment No: 7

Date:

PREPERATION OF BENZAMIDE FROM BENZOYL CHLORIDE

AIM

To prepare and submit benzamide from benzoyl chloride

REQUIREMENTS

Apparatus: Beaker, iodine flask, funnel.

Chemicals: Ammonia, benzoyl chloride, sodium hydroxide.

PRINCIPLE

Benzoyl chloride is a functional derivative of carboxylic acid undergoes

nucleophilic acyl substitution reaction with ammonia and forms benzamide.

PROCEDURE

Placed a mixture of 10ml concentrated ammonia solution and 10ml water in

an iodine flask. Added 2ml benzoyl chloride and corked the flask securely. Shaked
the flask vigorously for 15 minutes. The mixture becomes hot and for this reason,
throughout the shaking, hold the cork tightly in position, with the flask pointing
away from the operator. At intervals release the pressure by cautiously removing
the cork. Afetr vigorous shaking for 15 minutes, no trace of oily benzoyl chloride
should remain. Filtered off the fine flakes of banzamide, washed with cold water
and then recrystallized from hot water.

USE

Protect coronary smooth muscles.

Preperation of anti cancer drugs.

REPORT

Benzamide was prepared from benzoyl chloride and submitted.

The percentage yield of benzamide prepared was found to be...................

REFERENCE

Practical Pharmaceutical Chemistry II; Dr. A V Kosture, Dr. S G Wadokar;

Page No.: 54.
Experiment No: 8

Date:

PREPERATION OF ASPIRIN FROM SALICYLIC ACID

AIM

To prepare and submit aspirin from salicylic acid

REQUIREMENTS

Apparatus: Beaker, conical flask, funnel.

Chemicals: Salicylic acid, acetic anhydride, sulphuric acid and alcohol.

PRINCIPLE

It is based on acetylation resulting in esterification of compounds.

Acetylation proceeds readily with acetic anhydride in the presence of little
concentrated sulphuric acid as catalyst. Salicylic acid upon acetylation yields
acetyl salycilic acid. It decomposes when heated and does not possess a true,
clearly defined melting point.

PROCEDURE

2.5g of salicylic acid was weighed and placed in a dry conical flask. 3.5ml of
acetic anhydride and 2-3 drops of conc. Sulphuric acid was added to it. The flask
was shaken well and warmed on water to about 50-600C for 15 minutes. Then it
was cooled to room temperature. 75ml of cold water was added. The formed
precipitate was filtered and then dried.
USE

It is used as analgesic, antipyretic, anti inflammatory agent and

anticoagulant.

REPORT

Acetyl salicylic acid was prepared from salicylic acid and submitted.

The percentage yield of acetyl salicylic acid prepared was found to

be...................

REFERENCE

Elementary Practical Organic Chemistry Part I; Small Scale Preperations;

Arthur I Vogel; Page No.: 364- 365.

Experimental Pharmaceutical Organic Chemistry; K S Jain; Page No.: 190-

191.

Essentials of Medical Pharmacology; 6th Edition; Jay Pee; K D Tripathi;

Page No.: 187- 193.
STEREOMODELS
 STEREOMODEL OF METHANE

AIM

To study the stereomodel of methane.

REPORT

Stereomodels of methane was studied.

REFERENCE

Advanced Organic Chemistry; Arun Bahl and B S Bahl; Page No.:

184- 185.
 STEREOMODEL OF ETHANE

AIM

To study the stereomodel of ethane.

REPORT

Stereomodels of ethane was studied.

REFERENCE

Advanced Organic Chemistry; Morrison and Boyd; Page No.: 122-

123.
 STEREOMODEL OF ACETYLENE

AIM

To study the stereomodel of acetylene.

REPORT

Stereomodels of acetylene was studied.

REFERENCE

Advanced Organic Chemistry; Morrison and Boyd; Page No.: 411-

413.
 STEREOMODEL OF BENZENE

AIM

To study the stereomodel of benzene.

REPORT

Stereomodels of benzene was studied.

REFERENCE

Advanced Organic Chemistry; Arun Bahl and B S Bahl; Page No.:

968- 969.
 STEREOMODEL OF KETONE

AIM

To study the stereomodel of ketone.

REPORT

Stereomodels of ketone was studied.

REFERENCE

Advanced Organic Chemistry; Arun Bahl and B S Bahl; Page No.:

564-565
SYSTEMATIC QUALITITIVE ANALYSIS OF
ORGANIC COMPOUNDS
SYSTEMATIC QUALTITIVE ANALYSIS OF UNKNOWN
ORAGNIC COMPOUND