Results:
Figure 1:
TLC plates no pictures, actual plates
Table 1:
Reaction Product
|
Mass
|
Recovery %
|
Melting Point ℃
|
Starting Material
|
0.612 g
|
---
|
---
|
Crude
|
0.578 g
|
94.6 %
|
131-133
|
Recrystallized Product
|
0.239 g
|
39.05 %
|
135-137
|
Table 2 TLC analysis for the plates:
TLC Plate 1:
Spot
|
Compound
|
Solvent Front
|
Spot distance
|
Rf
|
Conclusion
|
A
|
Benzoin
|
4.4 cm
|
3.4 cm
|
.77
|
Compound was benzoin
|
B
|
Recrystallize product
|
4.4 cm
|
2.4 cm
|
.54
|
Compound was 1,2-diphenylethane-1,2-diol
|
C
|
Co spot
|
4.4 cm
|
Spot 1: 3.3 cm
Spot 2: 2.5 cm
|
Spot 1: .75
Spot 2: .56
|
Contained Benzoin and 1,2-diphenylethane-1,2-diol
|
TLC Plate 2:
Spot
|
Compound
|
Solvent Front
|
Spot distance
|
Rf
|
Conclusion
|
A
|
Benzoin
|
4.4 cm
|
3.5 cm
|
.79
|
Compound was benzoin
|
B
|
Crude
|
4.4 cm
|
2.5 cm
|
.57
|
Compound was 1,2-diphenylethane-1,2-diol
|
C
|
Co spot
|
4.4 cm
|
Spot 1: 3.4 cm
Spot 2: 2.6 cm
|
Spot 1: .77
Spot 2: .59
|
Contained Benzoin and crude product
|
Discussion:
In this experiment, benzoin was reduced with sodium borohydride and recrystallized to 1,2-diphenylethane-1,2-diol(0.239 g) with a recovery of 39.05 %. The product, (1,2-diphenylethane-1,2-diol), was determined through TLC analysis and melting point. The TLC analysis showed the presence of two different compounds (seen in Figure 1). The starting material (spot A) traveled the same distance on both the TLC plates with Rf values of .77-.79 which are very close. This is different than the recrystallized product and the crude product (spot B) in plates 1 and 2, respectively. The recrystallized product and the crude product travel a shorter distance and therefore have a lower Rf value that are very similar to each other, .54 and .57 respectively. The co spots (spots C) show that there are two compounds presence since both contain two spots with two different Rf values.
This means that a starting material other than the starting material has formed in both the crude and the recrystallized product. Additionally spot B on both plates contain only one spot and neither matches the starting material spot so therefore Benzoin (starting material) must not be present in the crude and recrystallized product.
The TLC plate is a silica gel plate that is polar, which means polar compounds interact more with the plate and don’t travel as far as relatively less polar compounds. Benzoin was expected to travel further than 1,2-diphenylethane-1,2-diol because it is less polar. This was supported by the TLC plate and observations made. The melting point also supported that the recrystallized product (1,2-diphenylethane-1,2-diol) was relatively pure as it’s MP range was 135-137 ℃, which is two degrees, signifying purity. The melting points for this lab is very important because it tells us how pure the substance is and in some cases is able to determine the isotope of a certain compound.
To improve purity a different substance other than HCl could be used to cause a slower reaction, which in turn would increase the purity of the product. Yield could be increased by raising the temperature slightly when mixing in this lab as it takes a long time for the solids to dissolve which could mean some is being left out or not completely dissolved. The warming would allow for all the starting material and materials involved to be used to their fullest.
Post Lab question:
This would mean that there would be 3 different compounds in the mixture.
The spot with the same Rf as the starting material is the starting material, and the other two spots with different Rf values are most likely the expected product, the secondary alcohol. The difference between the last two non starting material spots could be because they are different isomers of the same compound.
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