Benzoic Acid

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ORGANIC CHEMISTRY

SISP
EXPERIMENT NO: 13

PREPARATION OF BENZOIC ACID

AIM: To prepare and submit benzoic acid from benzanilide


APPARATUS: Round bottom flask, Reflux condenser, beaker, Funnel, Glass rod
CHEMICALS: Benzanilide, 70%H2SO4
PRINCIPLE: The principle involved in the preparation of benzoic acid from benzanilide is acid
catalysed hydrolytic reation. Benzanilide undergoes hydrolysis in acidic medium to yield benzoic
acid as colourless crystals. Aniline hydrogen sulphate being water soluble remains in solution
and solid benzoic acid separates out.
REACTION:

H2SO4

H20

PROCEDURE: A mixture of 1 gm of benzanilide and 10 ml of 70%H 2SO4 were placed in a


round bottom flask fitted with a reflux condenser. The mixture was boiled gently for 30
minutes.10ml of hot water was poured on the inner walls of the condenser to dissolve benzoic
acid which gets solidified in the condenser. The flask was cooled on ice bath. The benzoic acid
separates. The solid benzoic acid was filtered off, washed with cold water and dried.
Calculation:
Molecular weight of salicylic acid =138g
Molecular weight of benzoic acid= 180g
PHARMACEUTICAL CHEMISTRY

Page No.87

ORGANIC CHEMISTRY

SISP

197 g benzanilide

122g benzoic acid

1 g benzanilide

X g benzoic acid

X=1*122/197= 0.6g
Theoretical yield =0.6g
Practical yield= ----------------- g
Percentage yield = Practical yield/ Theoretical yieldx100=------------------------------%w/w
REPORT:
Benzoic acid is prepared and submitted.
Theoretical yield of Benzoic acid is------------------------Practical yield of Benzoic acid is ----------------------Percentage yield of Benzoic acid is --------------------------%w/w.
Question & Answers for Viva Voce:
1) What is the principle involved in the preparation of benzoic acid from benzanilide?
A) The principle involved in the preparation of benzoic acid from benzanilide is acid
2)
A)
3)
A)
4)
A)

catalysed hydrolytic reation.


Which compound on acid hydrolysis yields benzoic acid?
Benzanilide on acid hydrolysis yields benzoic acid
Give the molecular weight of benzoic acid?
122
What is hydrolysis?
Hydrolysis is a chemical reaction during which the bond is broken in a reactant by the
addition of water.

5) Saponification is an example for which type of reaction?


A) Saponification is an example for base catalysed esterification

PHARMACEUTICAL CHEMISTRY

Page No.88

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