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Chemistry 212
FALL 2015
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Chemistry 212
FALL 2015
Property
1-methylimidazole
1-bromobutane
[C4-mim]Br
KPF6
[C4-mim]PF6
Volume (ml)
Molar mass
(gmol-1)
Density (gcm3)
Amount
(mol.)
Mass (g)
0.20
82.10
0.27
137.02
219.12
184.06
283.96
1.03
1.27
2.50*10-3
2.50*10-3
2.50*10-3
2.50*10-3
2.50*10-3
0.21
0.34
0.55
0.46
0.71
0.52
Yield (%)
73
Appearance
Note: There is a discrepancy between the percentage yield quoted here and that I had
provided to the TA since I calculated the molar mass of [C4-mim]PF6 wrong and hence the
theoretical came out to be different.
Discussion Questions: (18 marks)*
1. Suggest one chemical reason, specific to this experiment, why your percent yield could
be less than 100%.
The reaction may have taken place via an E2 mechanism since the nucleophile is bulky and
the reaction to produce the initial ionic liquid was carried out at a very high temperature of
about 100C.
2. What is an ionic liquid? Why are they useful/important?
A liquid whose constituents are made of oppositely charged ions, held to each other by
electrostatic force of attractions is an ionic liquid. An ionic liquid is basically a salt.
Traditionally, the term ionic liquid is associated with salts in which the electrostatic force
of attraction between the anion and the cation is weak enough for its melting temperature
to be below 100C. Ionic liquids can be very useful as solvents as they have extremely low
vapour pressure (boils at very high temperatures), they do not breakdown, unless at very
high temperatures and they lack combustibility. So ionic liquids are safer and less wasteful
options than traditional solvents like hexane and ether, which have very high vapour
pressures and can produce harmful fumes.
* written component check General Report Guidelines for grammar requirements
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Chemistry 212
FALL 2015
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Chemistry 212
FALL 2015
References:
1) http://www.chemspider.com/Search.aspx?q=PF6
2) http://www.chemspider.com/Chemical-Structure.7711.html?rid=b34839c7-3045421e-8ffc-d81a95eb0e7d&page_num=0
3) http://www.chemspider.com/Chemical-Structure.1348.html?rid=ed385618-f1e34056-89c0-ef4f5720dd83
4) http://www.chemspider.com/Chemical-Structure.2015930.html?rid=9eaca17afd5d-4028-a2c5-543acdedbb6d
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