Experiment 1: Thin Layer Chromatography

Femi Ajayi; 8266716


CHM1321; Lab 4

January 26th 2016


 Lab Instructor: Indee Ranasinghe

Professor: William Ogilvie

 Reagent Table
Compound Mol.Mass(g/mol) Amount Density(g/ml) moles
2:8 EtoAc:Hexane 10 ml
Dichloromethane 84.93 2 ml 1.33 0.0313
Unknown #49 10 mg
Benzophenone 182.217 2 ml 1.11 0.0122
Biphenyl 154.21 2ml 1.04 0.0135
Ethyl Acetate 88.11 10 ml 0.897 0.102
Hexane 86.18 10 ml 0.655 0.076
Unknown-YY 2 ml
9:1 Hexane:EtoAc 10 ml
O- 202.01 1 drop 1.704
Bromonitrobenzene
M- 202.01 1 drop 1.704
Bromonitrobenzene
P- 202.01 1 drop 1.948
Bromonitrobenzene
Observations
Part 1:
 2:8 EtoAc:Hexane is a transparent liquid, while unknown #49 is a salt-looking white
opaque solid
 when unknown is mixed with transparent liquid dichloromethane it dissolves and solution
is also transparent
 as the tlc plates are put in the solution jar the plates absorbs the solution.
 After putting the plates under a UV lamp we can see the spots on the plates have moved
up from where they were initially applied
Part 2:
 Ethyl Acetate is a clear transparent liquid that becomes the new jar solution.
 After putting the new tlc plates in this solution the spots under the UV lamp are very high
up on the plates
 Hexane is also a clear transparent liquid that is used as a new solution inside of the jar.
 When the new tlc plates are put in the jar the spots for the benzophenone do not move
while the spots for the biphenyl move, but less in comparison to the ethyl acetate solution
tlc plates.
Part 3:
 A drop of O, M, P-bromonitrobenzene are used as references for three different tlc plates.
 They are placed in a jar with a transparent solution of 9:1 Hexane: Ethyl Acetate.
 The M and P plates absorb normally however the O plate does not absorb as much
solution as the other plates.
 All of the drops move up from their applied spots
 TLC Plates (Silica Gel)
Solvent System: 2:8 EtoAc:Hexane
(Left spot-Reference) (Middle spot- Co) (Right Spot- Sample)
Part 1: Unknown #49
Benzophenone 2:8 Ethyl Acetate-Hexane

Solvent System-2:8 EtoAc:Hexane Benzophenone Rf= 0.65 Unknown #49 Rf= 0.64
Biphenyl 2:8 Ethyl Acetate-Hexane
 Solvent System-2:8 EtoAc:Hexane Biphenyl Rf= 0.80 Unknown #49 Rf= 0.62
Part 2: Unknown #49
Benzophenone Ethyl Acetate

Solvent System:Ethyl-Acetate Benzophenone Rf= 0.88 Unknown #49 Rf= 0.0.88

Biphenyl Ethyl Acetate
Solvent System: Ethyl-Acetate Biphenyl Rf= 0.94 Unknown #49 Rf= 0.92
Benzophenone Hexane

Solvent System-Hexane Benzophenone Rf= 0.02 Unknown #49 Rf= 0

Biphenyl Hexane

Solvent System-Hexane Biphenyl Rf= 0.34 Unknown #49 Rf= 0.0

 Part C: Unknown YY
O-bromo 9:1 Hexane-Ethyl Acetate

Solvent System: 9:1 Hexane:EtoAc O-Bromonitrobenzene Rf= 0.44 YY Rf= 0.78 & 0.56
M-bromo 9:1 Hexane-Ethyl Acetate

Solvent System: 9:1 Hexane:EtoAc M-Bromonitrobenzene Rf= 0.5 YY Rf= 0.49 & 0.58
 P-bromo 9:1 Hexane-Ethyl Acetate

Solvent System: 9:1 Hexane:EtoAc P-Bromonitrobenzene Rf= 0.62 YY Rf= 0.52 & 0.63
 Discussion
 In part a the solvent system was 2:8 Ethyl Acetate:Hexane, the references used were
benzophenone and biphenyl
 Given unknown #49 mixed with dichloromethane, we placed the organic materials on the
TLC plates.
 We observed that the Rf of benzophenone 0.65, is similar to the Rf for unknown #49
which is 0.63.
 Biphenyl had the highest Rf
 with this we estimated that unknown 49 had similar polar properties as benzophenone
 biphenyl is the least polar of all three
 in TLC, the less polar an organic material the higher up the plate it goes.
 Biphenyl is completely non-polar so it goes higher up the plate
 Benzophenone contains a polar carbonyl group but is still non polar
 This group makes it move slower than biphenyl because the carbonyl group is attracted to
the silica gel.
 Since the unknown 49 has a similar position on the plate we can guess that it is a non
polar chemical with a polar group of some kind.
 I believe mixture of Unkown #49 is either Benzophenone or a compound similar to it.
 In part b the solvent system is changed twice using Ethyl Acetate and Hexane, while the
organic materials remain the same.
 With solvent system Ethyl Acetate the Rf values of Benzophenone was 0.88 the average
of unknown 49 was .90 and the Rf of biphenyl was 0.94
 In TLC the distance that polar and non-polar compounds move can be increased by
increasing the polarity of the solvent.
 Ethyl Acetate is much more polar than 2:8 Ethyl Acetate:Hexane.
 Because of this the Rf of the organic materials significantly increases
 The opposite is also true. the distance that polar and non-polar compounds move can be
decreased by decreasing the polarity of the solvent.
 This is shown through the solvent system Hexane which is very non-polar.
 Hexane is a long carbon chain with many non-polar bonds which makes it very non-polar
and unlikely to dissolve in water.
 Because hexane is very non-polar it does not make the organic materials move up the
plates which gives benzophenone an Rf of 0.02 and #49 0.
 Biphenyl has an Rf of 0.34 because the solvent system is also non polar.
 The non-polar solvent dissociates the non-polar biphenyl making it easier to move up the
plates.
 In part c we used O, M and P-Bromonitrobenzene as reference material and YY as our
sample.
 The solvent system used was 9:1 Hexane-Ethyl Acetate which contains much more non
polar Hexane and a little polar Ethyl Acetate.
 The Rf for O-bromo was 0.44 and for YY it was 0.56 and 0.78
 With this we can say that O-Bromo is slightly more polar than any of the organic
materials in YY because its smaller Rf means it is more attracted to the silica gel than YY
 The Rf for M-bromo was 0.5 and for YY it was 0.49 and 0.58
 M-Bromo is less polar than O-bromo and has a similar Rf to the lower Rf of YY. This
means that M-Bromo has a similar polarity to the more polar part of YY.
 The Rf for P-bromo was 0.62 and for YY it was 0.52 and 0.63
 P-Bromo is less polar than both M and O-bromo and has a similar Rf to the higher Rf of
YY. This means that P-Bromo has a similar polarity to the more polar part of YY.
 Bromonitrobenzene has two substituent groups of Bromine(Br) and Nitrogen
Dioxide(NO2).
 The difference between them is that O-bromo has them on adjacent carbons, M-bromo
has one carbon in between their respective carbons and P-Bromo has them on carbons
opposite each other.
 O-Bromo is the most polar because the carbons of the substituent are adjacent giving that
side of the compound a higher electron negativity making it slightly more polar than the
rest
 P-Bromo is the least polar because the substituent groups are opposite each other which
slightly balances out the electron negativety charges. This makes it the least polar and
attracted to the silica gel. Giving P-Bromo the highest Rf.
 Peak 2 for O-Bromo is 67.36%, peak 3 is 32.64%
 Peak 2 for M-Bromo is 28.57%, peak 3 is 71.43%
 Peak 2 for P-Bromo is 48.74%%, peak 3 is 51.26%
 Questions
1. Thin layer chromatography uses the concept of polar bonding to help increase and
decrease the distance compounds move up the silica gel. The more polar compounds are
the more they are attracted to the silica gel, which makes it harder for them to move up
the gel. However, to counteract this, one can increase the polarity of the solvent which
will disrupt the intermolecular forces between the silica gel and the compound, helping
the compound move higher up the plate.
Raw Data Sheet