CHM 624

ADVANCED
ORGANIC
EXPERIMENT 2
PREPARATION OF 4-BROMOBENZOPHENONE
BY FRIEDEL-CRAFTS REACTION
NORHAFIZOH BT ABDUL SOMAT
2011353063
DATE OF EXPERIMENT: 10 & 17/ 3/2014
LECTURERS NAME: PM DR RAZALI IDRIS
LAB GROUP MEMBERS: NIK AINU MD NOR
NORAZIAH MOHD TAHIR
FATIMATUZZAHARAH ABDUL RAZAK

OBJECTIVE
To prepare 4-bromobenzophenone using Friedel-Crafts reaction

INTRODUCTION
The introduction of an acyl group into an aromatic ring is accomplished by an
electrophilic substitution by the acylium ion generated by the reaction between
an acyl halide and aluminium chloride. In bromobenzene, the benzene is a
deactivating and ortho , para-directing substituent. However this reaction gives
mainly para-isomer, presumably ortho-substitution which might also be expected
is sterically less favoured.

PROCEDURE

Bromobenzene and benzoyl chloride are placed in 50mL Erlenmeyer flask

Aluminium Chloride is added in 3 portions, shaking, and stirring in
between additions
The flask is heated on boiling water bath for 20 min.
The dark red liquid is cooled and poured onto ice and the remaining
contents is washed out by careful addition of 10% NaOH to the flask
The combined solutions are made alkaline by addition of 10% NaOH
solution to dissolve any benzoic acid present and aluminium salt.
The alkaline solution is heated
The solution is removed the brown oily precipitate is collected.
The brown oily precipitate is dissolved in water with addition of NaOH and
ether
The mixture is extracted with ether 3 times
The organic extract is dried over MgSO4 and the ether is removed using
rotary evaporater
4-Bromobenzophenone is recrystallized from light petroleum to give
colourless solid
The yield and melting point is recorded, purified product is analysed using
IR spectroscopy

CALCULATIONS

RESULTS AND OBSERVATION

No product obtained from the experiment
The theoretical yield is 4.959g of 4-bromobenzophenone
Theoretical
melting
point
(http://www.chemicalbook.com/)

of

4-bromobenzophenone:

IR spectrum of 4-bromobenzophenone is shown in the next page

79-84C

DISCUSSION

CONCLUSION
No product is obtained from this experiment due to various errors discussed.
The theoretical yield is 4.959g of 4-bromobenzophenone

ANSWER TO QUESTIONS
Suggest synthesis of the following from benzene:

REFERENCES
http://www.chemicalbook.com/
http://www.hanhonggroup.com/
Solomons T.W.G, Fryhle C.B. (2011). organic chemistry. Asia: John Wiley & Sons
Inc.

OBJECTIVE
INTRODUCTION
PROCEDURE
RESULTS & OBSERVATIONS
CCALCULATIONS
DISCUSSION
CONCLUSION
ANSWER TO QUESTION
REFERENCES
PRE-LABORATORY PREPARATIONS

FULL MARKS
1
2
1
2
2
5
1
2
1
2

LABORATORY TECHNIQUES
TOTAL MARKS

1
20

MARKS