EXPIREMENT NO.

:- 1

AIM:- To prepare benzanilide from benzoyl chloride (Schotten-Bouman Reaction)

Requirement:- Aniline = 5.2g , NaOH = 45ml (10g in 100ml H2O) , Benzoyl chloride = 8.5g ,
Alcohol = 8.5g
Theory :- The Schotten-Bouman reaction is a method to synthesise amides from amines and acid chlorides.
Sometimes the name for this reaction also used to indicates the reaction b/w an acid chlorides and an
alcohol to form an ester . The first reaction was first described in 1883 by German Chemist Carl Schotten
and Eugen Bauman.
Reaction:-
C6H5NH2 + C6H5COCl + NaOH C6H5NHCOC6H5 + NaCl + H2O
Mechanism:-

C6H5
-H O
C6H5C -C l
C6H5NH2 + Cl C6H5 NH3 C Cl C6H5 NH C C6H5 C6H5NHCOC6H5
O O
Cl

Procedure:-
1) Took 5.2g of aniline 8.45ml of NaOH in a stappered flask.
2)Add benzoyl chloride shake vigrously for 15-20min, flask becomes hot.
3) Reaction completed when there is no smell of benzoyl chloride, then stop shaking.
4)Product was separated out as white. Product was checked whether alkaline or not.
5) 100ml of cold water was added and then filtered with buchner funnel washed with cold water.
Application:-
These reaction condition are widely used today in organic chemistry.
Examples:-
1) To synthesize capsaiem.
2) To synthesis benzamide.
3)Acetylation of benzylamine with acetyi chloride in the Fischer peptide synthesis.
Precaution:-
1)Carefully shake the bottle containing chemicals.
2) Stop shaking only after the smell at benzoyl chloride not felt.
3) Carefully handle the glass apparatus.
4) Wear lab coat and gloves.
Observation:-

Name of Compound Benzoyl Chloride Aniline Sodium Hydroxide

Mol. Formula C6H5COCl C6H5NH5 NaOH
Mol. Mass 140.5 93 40
Weight Taken (g) 8.5 6.2 4.5
Volume Taken 7.024 6.089 4.5
Moles .060 0.055 0.11
Density

Calculation:-
92g of aniline gives = 197g of benzanilide
1g of aniline gives = 197/92 of benzanilide
5.2g of aniline gives = (197/92)*5.2 of benzanilide
= 11.01g
Observed yield = 8.8 gm
%age yield = 79.92%

UV Spectrum:-

IR Spectrum:-
NMR:-

Result:-
Theoretical Yield =11.01gm
Observed Yield =8.8gm
Observed M.pt =1580C
Literature M.pt =1630C
%age yield =79.92%