GRIGNARD SYNTHESIS

Syntheses of Phenylmagnesium bromide and Triphenylmethanol

Group 1
Sangalang, Reymart V.
Sucaldito, Melvir R.

Dr. Glenn Alea

INTRODUCTION

REACTION AND MECHANISM

PROCEDURE
0.050 g of
magnesium
solid

2.2 mmol (0.232 ml) of

bromobenzene

0.5 ml anhydrous
diethyl ether

0.5 ml anhydrous
diethyl ether

Phenylmagnesium bromide
( Grignard Reagent)

PROCEDURE
0.364 g of
benzophenone

1.0 ml of anhydrous
diethyl ether

Phenylmagnesium bromide
( Grignard Reagent)

PROCEDURE

PROCEDURE

2ml of 3M HCl

The solution was place

in an ice bath.

PROCEDURE
A - Bromobenzene
B - Cospot
C Product
(Ether layer)
UV light as visualizing
agent
Solvent system:
1:5 DCM:Pet.ether
A

PROCEDURE
Aqueous layer was removed by
Pasteur Pipette
Saturated NaCl Solution was added

Anhydrous CaCl2 was added to dry

The ether extract was dried using

Nitrogen gas

PROCEDURE

Slightly yellowish
solid
Melting Point
FT-IR Analysis

Triphenylmethanol ?

RESULTS AND DISCUSSION

Phenylmagnesium bromide
Phenylmagnesium bromide reacted with
benzophenone

RESULTS AND DISCUSSION

A - Bromobenzene
B - Cospot
C Product
(Ether layer)
UV light as visualizing
agent
Solvent system:
1:5 DCM:Pet.ether
A

SPOTS

Distance of
Solvent

Distance of
Solute

Rf Value

28 mm

18 mm

0.643

28 mm

18 mm , 10 mm 0.643 , 0.357

RESULTS AND DISCUSSION

Weight of Test Tube w/ cap = 18.241 g
Weight of Test Tube w/ cap and sample = 13.569 g

Weight of the Crude Extract = 0. 328 g

Melting Range of the Crude Extract 43 47 0C

Theoretical Melting Point :
Triphenylmethanol 164.2 0C
Benzophenone 48 0C

RESULTS AND DISCUSSION

A - Benzophenone
B - Cospot
C Product
UV light as visualizing
agent
A

Solvent system:
1:5 DCM:Pet.ether

SPOTS

Distance of
Solvent

Distance of
Solute

Rf Value

25 mm

8 mm

0.32

25 mm

5 mm

0.20

RESULTS AND DISCUSSION

A. Crude Product

Pertinent Peaks

Functional Group

3454.24 cm-1 (medium)

-OH

3059.16 cm-1 (medium)

sp2 -CH

1657.18 cm -1 (strong)

-C=O

A. Triphenylmethanol

A. Benzophenone

Pertinent Peaks

Functional Group

Pertinent Peaks

Functional Group

3474 cm-1 (strong)

-OH stretch

3433.241 cm-1 (weak)

-OH

3087 cm-1 (medium)

sp2 -CH stretch

3050.70 cm-1 (weak)

sp2 -CH

1150 cm -1 (medium)

-C-O bending

1651.00 cm -1 (strong)

-C=O

CONCLUSION

The Grignard reactions are generally used by chemists due to its versatility. In
this experiment, the syntheses of phenylmagnesium bromide, the Grignard
reagent, and triphenylmethanol were performed.

The synthesis of Grignard reagent must take place in an inert and anhydrous
solvent, ideally anhydrous diethyl ether, using bromobenzene and magnesium
solid. The reaction is exothermic and must be kept closed until reaction ceases
to prevent water contamination. This is the most crucial stage of the synthesis
since absence of water must be maintained.

The Grignard reagent must be reacted immediately with the ketone,

benzophenone, to form the alkoxide and upon acidification, the product,
triphenylmethanol is formed. The product was dried, weighed and subjected to
Thin Layer Chromatography.

CONCLUSION

The mass of the crude extract is 0.328 g. The mobile phase used is 1 DCM:5
petroleum ether. The results for TLC shows that the synthesis and isolation of
the desired product is unsuccessful. This is further confirmed by melting point
determination, the melting range of the product was 43-47C. The IR spectra of
the product is similar with benzophenone, one of the reactants. It is concluded
that the synthesis of phenylmagnesium bromide was successful and the
synthesis for triphenylmethanol was not.

RECOMMENDATION

In performing the experiment for the synthesis of phenylmagnesium bromide, it

is highly recommended to keep the system dry and free from contamination.
All glasswares must be preheated at least 30 minutes to ensure dryness and
cleanliness.

It is recommended to use analytic grade anhydrous diethyl ether, use proper

container and proper transferring must be done to ensure water-free ether. The
magnesium, bromobenzene and benzophenone must be dried also.

For the activation of magnesium, it is recommended to use iodine as activator

for magnesium and indicator for the reaction so as to avoid the exposure of the
mixture to air.

It is recommended to perform TLC analysis as frequent as possible to monitor

the progress of the reaction and the formation of the product.

DOMO ARIGATO
GOZAIMASHITA!!!!