Mohit Vaghela

Locker number: 108

30/11/14

Experiment 2 Some Group 14 Chemistry and

NMR Spectroscopy
Method
Preparation of tribenzyltin chloride(IV) (Mr =427.55 g mol-1)
A mixture of tin powder (4.50 g) and water (40 cm 3) was formed which was
brought to boil whilst being rapidly stirred. Benzyl chloride (4.50 cm 3) was added
to the mixture over a period of two minutes and left to reflux for 2 hours. The
mixture was then cooled, gravitationally filtered and dried in air. The solid was
then dissolved in some hot acetone and the solvent was removed by evaporation
to obtain a crude product. The crude product was then recrystallized from the
minimum volume of warm ethyl acetate. The product was then collected and
dried by filtration under a vacuum (Yield: 0.19 g, 2.34%)(Melting point: 139142oC).

Preparation of cyclo-(Ph2SiO)4 (Mr = 793.17 g mol-1)

Step 1 Preparation of diphenylsilanediol (M r = 216.31 g mol-1)
A mixture was made up of toluene (2 cm 3), t-butanol (4 cm3) and water (16 cm3)
and stirred for 5 minutes allowing the mixture to return to room temperature. A
solution was made by dissolving diphenyldichlorosilane (4 cm 3) in dry toluene (2
cm3) and then was added to the mixture of t-butanol carefully while being stirred
ensuring that the mixture did not exceed 25oC. The mixture was stirred for
another 5 minutes and then filtered, washed with water (3 cm 3) and diethyl ether
(3 cm3) and dried under vacuum. (Yield: 5.03 g, 122%).
Step 2 Preparation of cyclo-(Ph2SiO)4 using diphenylsilanediol
A solution was made up of diphenylsilanediol (1.00 g) dissolved in ethanol (10
cm3). Three drops of 4M sodium hydroxide were added to the solution and was
left to reflux for 20 minutes. A white precipitate was formed. The solution was
cooled and the crude product was filtered under a vacuum. The crude product
was recrystallized by the minimum amount of warm ethyl acetate. The solution
was then gravitationally filtered and cooled. A white solid was formed when the
solution was cooled and was collected and dried by filtration under a vacuum.
(Yield: 0.14 g, 15.3%)(Melting point: 200-203 oC). A second crop was isolated by
cooling the mother liquors further (Yield: 0.04 g, 4.35%).

Yield Calculations
Tribenzyltin chloride (IV)
Relevant equation: 2Sn + 3C6H5CH2Cl Sn(C6H5CH2)3Cl + SnCl2

Mohit Vaghela

Locker number: 108

Limiting reagent: Tin (Sn)

Moles of Sn

4.50 g
=0.038 moles
118.7 g mol1

Ratio 2:1 therefore moles of Sn(C6H5CH2)3Cl

Expected mass

0.038
=0.019 moles
2

0.019 427.55 g mol 1=8.10 g

Actual mass = 0.19 g

Yield ( )=

0.19 g
100=2.34
8.10 g

Diphenylsilanediol
Relevant equation: SiCl2(C6H5)2 + 2H2O (C6H5)2Si(OH)2 + 2HCl
Limiting reagent: Diphenyldichlrosilane (SiCl 2(C6H5)2)
Density of Diphenyldichlorosilane: 1.204 g/cm3
Mass of Diphenyldichlorosilane

Moles of SiCl2(C6H5)2 =

1.204 g
4 cm3=4.816 g
3
1cm

4.816 g
=0.019 moles
253.2 g mol 1

Ratio 1:1 therefore moles of diphenylsilanediol = 0.019 moles

Expected mass

0.019 moles 216.31 g mol 1=4.11 g

Actual mass = 5.03 g

Yield ( )=

5.03 g
100=122
4.11 g

Cyclo-(Ph2SiO)4 [Crop 1]
Relevant equation: 4(C6H5)2Si(OH)2 Cyclo-(Ph2SiO)4 + 4H2O
Limiting reagent: (C6H5)2Si(OH)2

30/11/14

Mohit Vaghela

Moles of (C6H5)2Si(OH)2

Locker number: 108

30/11/14

1.00 g
=4.62 103 moles
1
216.31 g mol
3

Ratio 4:1 therefore moles of cyclo-(Ph2SiO)4

Expected mass ( 1.16 10

Actual mass = 0.14 g

Yield ( )=

0.14 g
100=15.3
0.92 g

Cyclo-(Ph2SiO)4 [Crop 2]
Actual mass = 0.04 g

Yield ( )=

0.04 g
100=4.35
0.92 g

4.62 10
=1.16 103 moles
4

) 793.17 g mol 1 =0.92 g