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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

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.6g Theoretical yield =0. Theoretical yield of Benzoic acid is------------------------Practical yield of Benzoic acid is ----------------------Percentage yield of Benzoic acid is --------------------------%w/w.6g Practical yield= ----------------. 5) Saponification is an example for which type of reaction? A) Saponification is an example for base catalysed esterification PHARMACEUTICAL CHEMISTRY Page No.g Percentage yield = Practical yield/ Theoretical yieldx100=------------------------------%w/w REPORT: Benzoic acid is prepared and submitted.ORGANIC CHEMISTRY SISP 197 g benzanilide 122g benzoic acid 1 g benzanilide X g benzoic acid X=1*122/197= 0.88 . 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.