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Organic Lab 343
IDENTIFICATION OF 2 UNKNOWN SOLIDS AND A LIQUID
The first two lab sessions will be used to determine the identities of two solid compounds and 1 liquid from a posted list of unknowns. One solid will be provided on a macroscale level and the other will be microscale quantities. Both will be “dirtied up” to make purification more interesting. This means that both compounds will need to be purified before obtaining a reliable, accurate melting point. Both macro- and microscale recrystallization techniques will be used to purify the unknown compounds. A general procedure for identifying your unknown macroscale solid has been provided and it will also serve as a guide for writing both of your final lab reports. Two lab reports worth 100 points each will be submitted. Each report will be due 48 hrs. after the completed lab session. For all unknown solids, be sure to record an unknown letter and the initial mass you obtain. For the unknown liquid, the boiling point will be determined using microscale methodology. You will perform the microscale method often referred to as Siwoloboff’s method
, described in Zubrick. The liquid samples provided are pure, so preliminary purification (distillation) is not necessary
. Be sure to write down the names of the 4 liquid unknowns before the second session so that you can come prepared with a table of their boiling points
. Although the boiling point will be used as the method of identification, what other physical properties may help distinguish the four liquids? Include the answer in your lab report LEARNING TARGETS The primary purpose of this lab is to give hands-on experience with the following basic laboratory techniques: o
Melting point determination o
Recrystallization (including how to conduct both gravity and vacuum filtrations) o
Microscale boiling point determination Other goals include: o
Honing observational skills in the lab o
Promoting good scientific writing skills (i.e., how to write a well-organized, complete lab report). PLEASE use proper scientific writing for your report which includes NOT using the first-
person narrative such as “Then
I
added hot methanol….” The proper reporting would be “Then hot methanol was added…”
Most importantly, try to make the connection between what is observed about physical processes (melting, boiling, crystallization) and what is going on at the molecular level. This should be part of the Discussion in Lab report 2. ORGANIZATION
You will organize your work and results in written lab reports. All lab reports contain basic information: date, title, objective, procedure, observations, data, calculations, results, and discussion/conclusion. Please see the rubric for “Writing a Technique Lab”.
For each lab session, note the objectives and pertinent physical data in your notebook/laptop before your lab session. Later, you will also include reactions. You must also bring a procedure to follow which you will then record in your notebook as you perform the experiment. Every student’s report is different, but the m
easure of a good scientific report is that it contains all the information necessary for someone else to repeat or duplicate your work. You may write procedures and observations side-by-side with procedures described on the left of the page and any observations and initial data on the right. Data will also be organized and presented in a separate section. TAs will discuss the format of lab reports. PROCEDURE 1) A macroscale unknown will be assigned. Record the letter designation of your unknown in your notebook. Weigh out approximately 1.0 g of the unknown and record the exact mass. Describe it: does it appear homogeneous or are there obvious flecks of impurities? What color is it? Is the solid crystalline or amorphous?
Organic Lab 343
2) Obtain a crude melting point and describe what you see. The ramp rate should be 10 o
C/minute and the starting temperature should be around 35 o
C (Check the list of unknowns). Is the melting point sharp or did it cover a broad temperature range? Report the range. Did all of it melt? Was the phase transition from solid to liquid clean or did discoloration (decomposition) occur? Look at the list of unknowns to know the highest melting point possible (and hence, a stopping point in case some solid doesn
’
t melt). 3) From this first melting point range, consult the list of possible unknowns and narrow down the possibilities as to which unknown you have. The next step is to purify it/recrystallize it. Please read Zubrick on recrystallization very carefully
. Test the suggested solvent or solvent combination for recrystallization. To do this, first try dissolving a small amount (microspatula tip-full) of your compound in a small amount (0.5 ml) of solvent in a test tube. If most dissolves and only a little remains insoluble even with w
arming that’s a good indication that
at least one impurity can be removed by simple gravity filtration. Do it and describe it. (Hint: Heat a beaker full of water and use it to heat the sample in the test tube). Note
: often a mixed solvent combination is suggested on the list of solid unknowns posted in the lab. An example would be “methanol/water”. The first solvent (methanol) is the one
in which the solid is quite soluble. The second (water) is the one in which it is only spari
ngly soluble. BE SURE to read Zubrick’s procedure for recrystall
ization using a mixed solvent system. 4) If your solution is discolored after dissolution in your (warm) solvent, it probably contains a soluble colored contaminant. It will be necessary to add a little charcoal (activated carbon), or Norit, to decolorize it. Don’t add too much or it will adsorb your compound. It is often necessary to gravity filter the solution more than once to remove the charcoal. Include a hand-drawing of a gravity filtration set-up. Only 2 treatments with charcoal should be done. If a bit of color remains, it
’
s okay. Move on to the next steps due to time constraints. 5) Once you have a homogenous solution of your solid and solvent: Recrystallize and describe everything you do. What solvent or solvent combo did you use? Was heating necessary for dissolution? Was icing necessary? Did you need to scratch the glass wall of the container to initiate crystallization? How long before crystals appeared? What did the crystals look like in comparison to the initial sample? 6) Isolate your purified product and describe everything. Include a hand-drawn picture of the vacuum filtration set-
up. What solvent did you use to wash your crystals? Was it cold or hot? What did the filtrate (mother liquor) look like? Did additional crystals form in the mother liquor? Did you harvest them? What was the appearance of your final, purified product? Are the crystals plate-like, needles, shiny? What was the mass of the final product? Calculate and report percent recovery. What was the melting point of the final product? A range should be reported for the melting point temperature and 2 melting points should be done. STOP HERE FOR FIRST LAB SESSION POST LAB QUESTIONS FOR FIRST LAB REPORT 1. Zahra was collecting her pure crystals via vacuum filtration from a methanol/water mixed solvent system. She poured the solution containing her crystals into the Büchner funnel. Then she rinsed her flask with some warm methanol and poured that over the crystals resting in the Büchner…
oops! Tell what happened and why. What should she have done instead? 2. Carleigh was taking the melting point of her crude unknown solid. She noticed some liquid formation at 116 o
C
–
120 o
C and waited for the rest of the solid to melt. At 400 o
C, the solid was still present. What could be happening with her sample and what will she likely have to do during the purification process?
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PART ONE: Preparation of FECNS* Solution
Prepare the two solutions in table 1 by accurately measuring the required volumes of distilled
water and CNS into two labeled test tubes. The absorbance of the solutions must be measured
soon after adding the Fe" solution from a buret.
TABLE 1
Fe
5 ml
5S mL
Solution
Distilled Water
CNS
2 mL
Total Volume
3 ml
2 ml
10 ml
3 mL
10 ml
In this part of the experiment you are to explore what the above quote means. As a
PRELIMINARY Exercise, formulate a hypothesis as to what would happen under each of the
following circumstances:
1. 1ml of 0.0020 M CNS' solution is added to the unused portion of
solution 1 in the test tube
2. One drop of 0.20 M CNS solution is added to the unused portion of
solution 2 in the test tube.
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%3D
What is the approximate Bromine Number?
O 138
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O 120
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Post-lab Questions
1. What would it mean if the melting point had a wide range in temperature rather than a
narrow range of one to two degrees?
Normal
BIIIU
X2| X² I →
fx |
Ix
2. Is your percent recovery of crystals within reason of what you would expect? Explain your
anwer.
Normal
BIIIU
X2| X² | →
fx |
|图|二
3. If you had chosen petroleum ether instead of your solvent what would happen?
BII|U
X2| X² | →
fx |
Ix
Normal
4. Would there have been a change in your results if activated carbon was not added to the
solution before recrystallization?
BIIIU
X2| X² | →
Normal
fx |
|图||||
!!
!!
II
II
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Table 1. Known Compounds for Melting Point Experiment
COMPOUND
mp range (oC)
COMPOUND
mp range (oC)
1)
1,4-dimethoxybenzene
54-56
21)
4-nitroaniline
146-149
2)
2-phenylphenol
57-59
22)
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158-160
3)
diphenylacetylene
59-61
23)
salicylic acid
159-161
4)
2,4,6-trichlorophenol
64-66
24)
triphenylmethanol
160-162
5)
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68-70
25)
sulfanilamide
165-167
6)
methyl 3-nitrobenzoate
78-80
26)
4-bromoacetanilide
165-169
7)
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80-82
27)
itaconic acid
165-168
8)
vanillin
81-83
28)
d-mannitol
166-168
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wwwd ICTor, KI, IS.
traveled by the fastest compound divided by distance traveled by the slowest compound
ce traveled by the slowest compound divided by distance traveled by the fastest compound
ance traveled by the solvent divided by distance traveled by the compound
distance traveled by the compound divided by distance traveled by the solvent
23-The maximum quantity of a mixture that can be separated with a given efficiency by a particular process
a)-Capacity factor
b)-Delectability
c)-Efficiency
d-Load capacity
24- The distribution coefficient of a compound is 1 and its concentration in organic layer is 3 M. Then, its
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a)-4 M
b)-3 M
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Pp
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To 1 ml. of bromine water in a test tube add .5ml chloroform or carbon tetrachloride. Note
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Which layer is more colored?
What do you call such liquids which do not form a homogenous mixture?
Can you possibly make them homogenous?
How?
Transfer the mixture into a separatory funnel and add 2 ml. more of bromine water and
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How
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iii. You could differentiate between the two with TLC.
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BP
MP
ST
VP
H
H-C-H
CI
Methane, CH
carbon tetrachloride, CCI4
S
H `H
H'
H.
Dihydrogen sulfide, H2S
water, H2O
HH
H-C--O--H
H--C-C-ô--H
H H
ethanol, CH3CH2OH
Methanol, CH3OH
H Ö:
нон
H-C--C=ÖH
H--C-Ć--Ċ-H
H
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