Daniel Zhang TMT4122 Organisk kjemi laboratoriekurs

Gruppe 3, plass 16A 7. March 2017

Experiment 6 Reduction
Summary
In this experiment benzophenone was reduced to diphenylmethanol using the reducing agent NaBH 4.
Together with a benzophenone- and diphenylmethanol standard, the final product (0.75 g, 0.004 n, 80%)
and all three solutions together were analyzed using thin-layer chromatography. The result showed a clear
indication that the product is diphenylmethanol as its rf value (0.5) is the same as the stocks rf value is
the same. The benzophenones rf value was measured to be 0.66.

Theory
Organic redox reactions
In general chemistry redox reactions are about addition and subtraction of electrons in chemical reactions.
In organic redox reactions however, it is more important to focus on hydrogen and oxygen content,
namely where a reduction is the increase of hydrogen content and a decrease of oxygen content and vice
versa with oxidation. Thus the reaction from ex. benzophenone to diphenylmethanol is a reduction
reaction because the hydrogen content increased while the oxygen content decreased. More generally, a
carboxylic acid reacting to become aldehyde, then to alcohol and then to an alkane are all reduction
reactions because of the increase of hydrogen content (vice versa with oxidation). In terms of reducing
agents, NaBH4 can only reduce aldehydes and ketones.

Thin-layer chromatography
TLC is a technique that utilizes the property on how good materials wanders in the mobile phase, i.e.
when the solvent is drawn up into a special plate due to capillary forces. Because of this, TLC can be used
to (preliminary) identify both the material and the purity of the material. More specifically, a retention
factor Rf can be calculated from the TLC technique, which is:

The distance the substance have moved

Rf =
The distance the solvent have moved

Eq. 1: Equation to calculate the retention factor, Rf.

Thus, if a material is eluated together with its standard material and they have approximately the same Rf
value, it indicates that the material is the same as the standard material. If no other dots appear below or
above the mark, then it is pure because no other substances are present.

The Experiment
An unclear mixture of NaBH4 (0.25 g) and iced water (5 mL) is added to a stirred solution of
benzophenone (0.99 g) and ethanol (15 mL) when it turns clear. After letting the mixture stir for 40
minutes it is added to a beaker (150 mL) with ice (ca. 30 mL) and HCl (3 M, 6.5 mL) to stir for 5 minutes
before putting it in an ice bath for an additional 5 minutes. Then the solution with the precipitated product
is vacuum filtered and rinsed twice with ice water (2 x 20 mL) using a Bchner funnel before it is dried
for 15 minutes on vacuum. Then the product is weighed to be 0.75 g (0.004 n, 80% yield).

A solution of ethyl acetate and petroleum ether (1:4, 20 mL) is added with a filter paper to beaker (250
mL) before it is enclosed using aluminum foil. A straight line is drawn on a TLC-plate, ca 1. cm from the
Daniel Zhang TMT4122 Organisk kjemi laboratoriekurs
Gruppe 3, plass 16A 7. March 2017

short side. Then four tests are applied to the line (benzophenone standard, diphenylmethanol standard, the
product and all three together) and is placed in the beaker. When the solvent front is 1 cm away from
the top it is taken away from the beaker and a line is drawn at the solvent front. Then using UV light the
substances can be marked and the Rf values can be calculated.

Result & Discussion

From the experiment the produced product was 0.75 g (0.004 n / 80% yield), while the Rf values were 0.5
for the product and 0.66 for the benzophenone standard.

There was a 20% weight loss in terms of the produced product. After the product was precipitated in the
sour ice water, it was filtered in a Bchner funnel. However, the precipitate was sticky and part of the
product did not wash away into the filter paper. Another reason for the weight loss must be from when the
product is extracted from the filter paper into a watch glass, where it is impossible to remove all the
product from the filter paper. In addition, the watch glass was not weighed beforehand and thus the
product had to then be added into a weighed beaker to be weighed, losing additional product during the
procedure. These errors could add up to about 20%, which makes the final amount of product reasonable.

In terms of TLC the product had the same value of Rf as the diphenylmethanol, giving the product a high
probability of being diphenylmethanol. Of course the product could be something else with a Rf factor of
0.5, however in this experimental procedure that is not very likely.

Daniel Zhang Trondheim, 7. Mar. 2017

Vedlegg
1. Kan det brukes et annet reduksjonsmiddel? Hvis ja, nevn et eksempel.
Et sterkere reduksjonsmiddel kan brukes, ex. LiAlH 4
2. Hvilken annen metode kan brukes for bekrefte produktets renhet?
Smeltepunkt bestemmelse, benzofenon har smeltepunkt p 48.5 C mens difenylmetanol har smeltepunkt
p 24 C
3. Hvordan kan produktsrenheten forbredes?
Den kan forberedes ved for eksempel la reaksjonen foreg lenger en 40 minutter, eller bruke et sterkere
reduksjonsmiddel, som nevnt over.