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CHM 624
ADVANCED ORGANIC CHEMISTRY
EXPERIMENT 4: SYNTHESIS OF FLAVONE
NAME : NURYASMIN AFINA BT MUHAMAD SHUKERI
STUDENT ID : 2014444792
GROUP : AS 202 5A2
LECTURERS NAME : DR. ROPISAH BT ME.
DATE OF EXPERIMENT : 14TH OCTOBER 2016
GROUP MEMBERS
NURSYAHIRAH SYAHIDAH BT BAHARIM
NOR AZEAN NADHIRAH BT MOHAMED SANI
SHUHAILI BT RASHID
EXPERIMENT 4: Synthesis of flavone
STUDENT
ID
2014851768
2014885566
2014668164
OBJECTIVES:
i.
INTRODUCTION:
Flavone
Flavones (flavus = yellow), are a class of flavonoids based on the
backbone of 2-phenylchromen-4-one Apart from flavones other flavonoids
are
isoflavonoids,
derived
from
3-phenylchromen-4-one
structure
benzoyl
esters,
followed
by
rearrangement
in
base
to1,3-
and
benzaldehyde
under
Claisen
Schmidt
MATERIALS:
1. Preparation of 2-benzoyloxyacetophenone
2-Hydroxyacetophenone (FW 136.2) 2.46 mL, 2.72 g (20 mmol)
Benzoyl chloride (FW 140.6) 3.48 mL, 4.22 g (30 mmol)
Pyridine (FW 79.1) 5 mL
Hydrochloric acid (3%)
Methanol
PROCEDURE:
1. Preparation of 2-benzoyloxyacetophenone
The 2-hydroxyacetophenone is dissolved in 5 mL pyridine (dried
over KOH) in a 25 mL round bottomed flask. The benzoyl chloride is
added, the flask is fitted with a calcium chloride guard tube and the
flask is swirled to ensure mixing of the reagents. The temperature of
the reaction mixture rises spontaneously. The reaction mixture is left
for about 20 min or until no further heat is evolved. Then the
mixture is poured into a 250 mL beaker containing 120 mL
hydrochloric acid (3%) and 40 g crushed ice with good stirring. The
product is collected by suction filtration and washed it with 4 mL
cold methanol and then 5 mL water.The product is dried by suction
PREPARATION OF 2-BENZOYLOXYACETOPHENONE:
of beaker
: 59.5868g
of beaker + product
: 61.81664g
of 2-benzoyloxyacetophenone obtained : 2.22984g
Mass
Molar mass
2.72 g
= 136.15 g/mol
= 0.019978 mol
No. of mol benzoyl chloride
Mass
Molar mass
4.22 g
= 140.6 g /mol
=0.03001 mol
-Since no of mol of 2-hydroxyacetophenone is less than no of mol
benzoyl chloride, therefore 2-hydroxyacetophenone is the limiting
reactant!
Theoretical yield of 2-benzoyloxyacetophenone:
Mass=No of mol Molar mass
= 0.019978 mol 240.258g/mol
= 4.79987 g
Percentage yield =
=
Actual yield
Theoretical yield 100%
2.22984
4.79987 100%
= 46.46%
Melting Point
Observation
: 89C
: Oily yellow liquid was observed
DISCUSSION:
In this experiment, 2-hydroxyacetophenone is synthesised to
get flavone. Unfortunately, the result of flavone is not obtained
might due to some errors. The product at the end of this experiment
is oily yellow liquid which has been used to run in the Fourier
Transform Infrared Spectroscopy (FTIR) in order to get the spectrum
and to identify the functional groups that exist in the product. FTIR
was used to obtain an infrared spectrum of absorption or emission
of a solid, liquid or gas. Even though some cases when some
compound has similar frequencies absorbed, IR can still detect the
compound. Thus, the infrared spectrum can be used for molecules
as much as it can be used as fingerprint for human. (Pavia et al,
2009). The product that obtained in this experiment is 2benzoyloxyacetophenone.
CONCLUSION:
The product obtained was 2-benzoyloxyacetophenone which
weighed 4.79987 g, percentage yield of 2-benzoyloxyacetophenone is
46.46% and has the melting point of 89oC.
REFERENCES:
1) Kshatriya, R. B., Shaikh, Y. I., & Nazeruddin, G. M. (2013). Synthesis
of flavone skeleton by different methods. Oriental Journal of
Chemistry, 29(4), 14751487.
2) Solomons, T. W. Graham, and Fryhle, Craig B. (2002). Organic
Chemistry : Friedel-Crafts Acylation (pp. 671-673). (7th ed.), USA:John
Wiley & Sons, Inc.
3) Donald L. Pavia, Gary M. Lampman, George S. Kriz, & James R.
Vyvyan, (2009), Introduction to Spectroscopy (4th Edition), USA:
Department
of
Chemistry
Western
Washington,
University
Bellingham
4) http://www.organic-chemistry.org/namedreactions/bakervenkataraman-rearrangement.shtm. Retrieved on 25 October 2016.
Problems
1. Discuss the mechanism of the Baker-Venkataraman rearrangement.
2. Assign
the
spectroscopic
data
for
the
starting
FREQUENCY (cm-1)
1640.40
1487.44 & 1447.66
2-
1302.10
1023.89
961.77 & 836.65
752.99 & 736.67
Methyl bending
C-O alcohol
=CH bending
-CH3 oop. Bending
b) 2-benzoylaxyacetophenone
FREQUENCY (cm-1)
ASSIGNMENT OF THE
1641.54
1484.58 & 1448.27
1303.6
3393.95
961.23
755.24
PEAKS
C=O
Methyl and methylene
Methyl bending
-OH alcohol
=CH bending
-CH3 oop. Bending