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Recrystallization
t lli ti
Identification of an unknown
CHE-231
CHE 231 Organic Chemistry
University of Kentucky
Introduction
• One of the most common p
purification techniques
q
CCl4 carbon no no
tetrachloride
C 5H 12 pentane no no
C 6 H 14 hexane no no
C 7H 16 heptane no no
Solubility at Room Temperature (RT)
• Solute insoluble
in solvent at
Room temperature
• So heat the solvent
and test it for complete
solubility at high
t
temperature
t
Solubility at high temperature
H3C C OH dissolves in H OH
acetic acid water
both have OH
b th are highly
both hi hl polar
l
Length of Carbon chain
• C5 rule
– Structures with less than 5 carbons and a polar
function are water soluble
– Branched chain compounds are more soluble than
corresponding
di straight
i h chain
h i compounds.
d (b(branched
h d
lowers intermolecular forces and intermolecular
attraction.))
C H 3C H 2 O H s o lu b le in H 2 O .
CH3
OH in s o lu b le in H 2 O .
CH3
Solution
• Place solid (~100 mg) in Erlenmeyer flask w/
3-5 mL of solvent
• Heat up to B.P. (stir constantly)
• Add enough solvent to dissolve solute
• Perform hot filtration if needed
• Remove colored impurity w/ activated
charcoal [colored impurities get ADSORBED
(not absorbed) on the surface of charcoal]
Hot Filtration
• Removes insoluble impurities and activated
charcoal
h l
• Do not p
put crystals
y in oven!
Melting points
• Physical characteristic of pure compound
• IImpurity
it causes both
b th d
depression
i off M
M.P.
P and
d
melting to occur over wide range
• Tapp some p
powder ((~2-3 mm)) into capillary
p y
tube
• R
Record d ttemperature
t when
h fifirstt d
drop off
liquid appears and when the entire sample
is melted
SP3 C-H
CH
SP2 C-H
O-H C=O
SP3 C-H
H
C C
O O
C=O
H H
SP2 C-H O-H
I. R. of p-bromoaniline
SP2 C-H
NH2 C-Br
Br N
SP2 C-H H
I. R. of 4-cyanopyridine
N C N
H SP2 C-H
I. R. of p-anisic acid
SP2 C-H
C=O
O C O
SP3 C-H H C H
H H H SP2 C-H
Procedure
• Determine M.P. range of unknown provided
by TA
~ 100 mg KBr
How much sample should I use?
KBr pellet continued…
• Keeping press upright, tighten other bolt
• Paper
ape cop
copies
es o
of IR spect
spectra
aoof poss
possible
be
compounds are in stock room (CP 333);
electronic copies are available on Bb.
Some important aspects of the experiment for
writing post-lab
post lab
• Purpose
• M P ranges (for both
M.P. both, impure and pure sample)
• Solubility data for all test ran
• Percent recovery value with calculation
• IR spectrum & its analysis
• scuss o o
Discussion of results
esu ts
Post-lab:
Worksheet for this experiment is available on Bb.
Waste Disposal
•Make a table for waste disposal. For example,