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Lab SD:
Simple Distillation and Boiling Point Analysis
Purpose
In this experiment, you will familiarize yourself with the theory of distillation by purifying an unknown organic
compound by simple microscale distillation. You will the identify the unknown compound using boiling point and
density measurements.
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Simple Distillation
Background
Background
Distillation is one of the oldest and most common methods for the purification and identification of organic liquids.
It is a physical process used to separate chemicals from a mixture by the difference in how easily they vaporize. As
the mixture is heated, the temperature rises until it reaches the temperature of the lowest boiling
substanceinthemixture, whiletheothercomponentsof themixtureremainintheiroriginalphaseinthemixture. The
resultant hot vapor passes into a condenser and is converted to the liquid, which is then collected in a receiver
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Learning Objectives
Set up and perform a simple microscale distillation.
Use boiling point and density in identification of an organic compound.
Laboratory Skills
Perform a simple distillation.
Determine a boiling point.
Equipment
Reflux condenser
Joint grease
Boiling chips
10 mL round bottom
flask
Clamps
Ring stand
Water hoses
Rubber O-rings
Plastic caps
Aluminum block
Hot plate/stirrer
Hickman still
pH paper
Thermometer
Glass pipet
3 mL conical vial
Syringe
Centrifuge tube
Chemicals
Unknown organic
compound
DI water
References:
1.
Multiscale OperationalOrganicChemistry,
by JohnW. Lehman, custom edition,
Prentice Hall Publishing, New Jersey, 2009; pp. 679-691.
2.
Pavia, D.; Lampman, G.; Kriz, G.; Engel, R.,
Organic Laboratory Techniques
,
Saunders College Publishing, New York 1990; pp. 638-651.
Simple Distillation
flask. The other components of the mixture remain in their original phase until the most volatile substance has all
boiled off. Only then does the temperature of the gas phase rises again until it reaches the boiling point of a second
component in the mixture, and so on. The boiling point of a substance—determined by distillation—is a useful
physical property for the characterization of pure compounds. At any given temperature a liquid is in equilibrium
with its vapor. This equilibrium is described by the vapor pressure of the liquid.
The
vapor pressure
is the pressure that the molecules at the surface of the liquid exert against the external
pressure, which is usually the atmospheric pressure. The vapor pressure is a very sensitive function of temperature.
It does not increase linearly but in fact increases exponentially with temperature. The vapor pressure of a substance
roughly doubles for every increase in 10
∘
C.
When the vapor pressure of the liquid equals the applied pressure, the liquid boils. Thus, the
boiling point
of a
liquid is the temperature at which the vapor pressure equals the applied pressure. The normal boiling point of a
liquid is the temperature at which the vapor pressure of a liquid equals atmospheric pressure (1 atm). The boiling
point of a liquid is a measure of its volatility.
Simple distillation
involves a single equilibration between the liquid and vapor. This distillation is referred to as
involving one theoretical plate and is frequently in the organic chemistry teaching labs, when the liquid is relatively
pure to begin with (e.g., no more than 10% liquid contaminants). Essentially, a pure material is separated from a
non-volatile or from a solid contaminant. The liquid is contaminated by a liquid with a boiling point that differs by at
least 70
∘
C.
Theprincipleof
fractionaldistillation
isbasedontheestablishmentof
alargenumberof
theoreticalvaporizationcondensation cycles (theoretical plates): the apparatus of a simple distillation is modified by
inserting a fractionating column between the distillation flask and the distillation head, The fractionating column
provides a large surface area in which the initial distillate is redistilled and condensed again. This process continues as
the vapors rise up the column until the vapors finally make it into the condenser. These vapors and the final distillate
will contain a greater percentage of the lower boiling liquid. Continuous repetition of re-distillation process in
fractional distillation gives good separation of the volatile liquid components.
Microscale Simple Distillation
The complete micro scale simple distillation setup is shown in Figure SD.1 and consists of a round-bottom flask
containing the liquid and 2 – 3 boiling stones, attached to the bottom joint of a Hickman still head (Figure SD.1A).
A condenser is attached to the top joint. A thermometer can be suspended down the middle in order to record the
distilling temperature, with the bottom of the thermometer in the lower part of the Hickman head just below the
circular well (Figure SD.1C).
Thevaporof theheatedliquid risesupwardandiscooled andcondenseson eitherthe insidewallsof theHickman head or
on the walls of the condenser. The condensate then collects in the circular well at the bottom of the still. The well
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Simple Distillation
can contain as much as 2 mL of liquid. The Hickman still we use has a side port to help with the distillate’s removal.
Distillate can later be removed with the help of a Pasteur pipet after opening the port (Figure SD.1B).
Once removed, the liquid is transferred to a smaller vial and capped with a Teflon-sealed cap. By recording the
boiling point and the density of the collected liquid you can identify the liquid after comparing it to a known
sample.
Figure SD.1:
(A) shows the Hickman head with the side port closed. (B) shows the Hickman head with the side port
open so it can be accessed with a glass pipet. (C) shows the position of the thermometer in the Hickman head. The
image on the right shows the distillation setup.
Procedure
Safety Precautions
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Simple Distillation
Full-sleeved shirts, full pants and shoes (covering all areas of foot) must be worn at all times.
Wear splash-proof goggles at all times.
Gloves must be worn when handling chemicals.
All organic compounds are extremely flammable. Organic compounds can be toxic they may target organs like
liver kidneys and neural cells. Be careful not to breathe your product or get it on your skin. Please review SDS
notes before lab.
All chemicals should be handled in the hood to avoid inhalation.
No eating and drinking allowed in the lab.
Wash your hands after handling the reagents.
The aluminum block, hot plate and your glassware can become very hot. Please use caution as they can cause
severe burns.
If any chemical gets on your skin wash the area with tap water for at least 15 minutes. Check with TA if further
treatment is necessary. All liquid and solid chemical waste should be discarded in the waste containers
located in the dispensing hoods.
No flames should be used in the laboratory.
Experimental: Distillation Setup
1.
Lightly grease the tapering ground glass joint of a reflux (jacketed) condenser. Too much grease will cause
problems. Show to your TA before proceeding.
2.
Add approximately 5 mL of the unknown organic assigned by your TA to a 10 mL round bottom flask (this is
your distillation flask).
3.
Add 2-3 boiling chips to the distillation flask and securely clamp the neck of the flask to a ring stand. Make sure
the clamp is secure and clamped below the lip of the neck of the distillation flask.
4.
Attach the Hickman still to your distillation flask, the side port of the still should be properly capped and the
ground glassware joints are lightly greased.
5.
Connect water hoses to the greased reflux (jacketed) condenser.
6.
Attach the condenser to your distillation flask (make certain that your ground glassware joints are lightly
greased).
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Simple Distillation
7.
Secure all glassware joint connections with rubber O-rings and plastic caps.
8.
Connect the water hose from the lower nozzle of the reflux condenser (See
??
) to a faucet. The water hose
from the upper nozzle (outlet) should be placed in the sink at the back of the hood.
9.
Turn on the faucet valve slowly, until a gentle stream of water flows through the reflux condenser,
do not start
heating.
10.
Place an aluminum block with the slight depression facing up on a hot plate stirrer.
11.
Lower the 10 mL distillation flask into the heating well.
12.
Insulate the top of the distillation flask and lower part of the Hickman still by loosely wrapping with aluminum
foil.
13.
Make sure that water is
gently
flowing through the condenser before you begin heating.
14.
Suspend a thermometer (use a small O-ring or a clamp) down the middle of the condenser. The bottom of the
thermometer should be in the lower part of the Hickman still head (see
??
C) just below the circular well.
Safety Precaution
The top of the top of the condenser should be
open
to the air and not capped or sealed.
Have your TA check
your setup before you start heating.
Distillation
15.
Start heating with your heating plate dial set to 30% power. You can increase this setting later after consulting
with your TA.
16.
Using a glass pipet collect 3 distillate fractions during the distillation (from the side port, see
??
B):
•
The liquid (the forerun) which is collected before the temperature stabilizes (distillate fraction 1).
•
The liquid which is collected after the temperature has stabilized (distillate fraction 2).
•
When about 0.5 mL of impure liquid remains in the distillation flask (distillate fraction 3).
Record the temperature when each fraction is collected.
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Simple Distillation
17.
Record the boiling point range as when the solvent begins to boil and collect in the well to the temperature
once it stabilizes again.
18.
After collecting your last fraction, remove the flask from the Aluminum block and allow it to cool.
Do not distill
to dryness.
As the distillation apparatus cools, perform the other tests on your unknown.
Density and Solubility Test
19.
Transfer 0.25 ml (syringe) of distillate fractions B to a
pre-weighed
, clean, and dry 3 mL conical vial and
determine its density.
20.
Add 0.5 mL of distillate B to a clean and dry centrifuge tube to perform the solubility test.
21.
Add 1 mL of DI water to this tube. Cap and shake the tube a few times. Remember to vent.
22.
Remove the cap and place the tube in a beaker and allow the mixture to settle for approximately 2 minutes.
23.
One layer means the unknown organic is
miscible
with water (see Table SD.1). Two layers means unknown
organic is
immiscible
with water.
24.
Record your observations (one layer or two layers).
Comparison to Known Organic Compound
25.
Carefully disassemble the cooled distillation apparatus.
Do not wash glassware with water.
In the next step, use the condenser without cleaning.
26.
Consult Table SD.1 and select one of the organic compounds whose data (boiling point, density and solubility)
is nearest (boiling point will not be exactly the same) to your unknown’s data. Due to the differences in your
technique and experimental errors the observed data of your unknown may not match the literature value of
any compound.
Table SD.1:
Possible Unknown Organic Compounds
Substance
Solubility in Water
Literature Boiling Point
(
∘
C)
Literature Density
(g/mL)
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Simple Distillation
Cyclohexane
Poor - Miscible
80-81
0.779
Methyl Alcohol
Very Good - Miscible
64-66
0.792
Hexane
Poor - Immiscible
68-69
0.654
Ethyl Acetate
Poor - Immiscible
76-78
0.902
Ethyl Alcohol
Very Good - Immiscible
77-79
0.789
27.
Perform the solubility test and determine the density of the organic compound you believe to be your
unknown.
28.
Determine the boiling point of the organic compound you believe to be your unknown by attaching a reflux
condenser to a clean 3 mL conical flask.
You do not need a Hickman still.
Suspend a thermometer (use the
same thermometer) down the middle of the condenser. The bottom of the thermometer should be slightly
above the liquid in the flask.
29.
When you have completed all the tests and recorded the data, ask your TA if you can start cleaning up.
Cleanup
30.
Clean up your bench and hood area. All the chemicals should be discarded in the appropriate waste container.
You do not need to clean your glassware with water.
31.
Wipe off the excess grease from the glassware.
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Introduction
Draw the chemical structures for ethyl acetate, acetone, methyl alcohol, cyclohexane, ethyl alcohol, and
n
-
hexane.
Experimental
Inashortparagraph, describetheset-upof thedistillationapparatusandtheprocessof distillation, including what
the sample was doing at each step.
Simple Distillation Report Sheet
Results
Unknown Compound Assigned: A / C / M / F / K / O
Report Table SD.1:
Distillation Temperatures of Unknown
Distillate fraction
Temp when collection started (
∘
C)
1
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Report Sheet:
Simple Distillation
Name:
Section:
Date:
2
3
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Organic compound assumed to be unknown (from Table SD.1):
Report Table SD.2:
Characterization of Unknown and Assumed Compound
Data indicates that unknown organic ( A / C / M / F / K / O ) is:
Simple Distillation Report Sheet
Discussion
Justify your identification of your unknown based on its behavior in the distillation and the characterization
tests.
Explain the difference in boiling point between your unknown and the other solvents. For example, you can
discuss hydrogen bonding, polarity, molecular weight, whether the structure is branched or linear, etc.
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Unknown-Fraction 2
Known-Assumed compound
Temp. at boil start (
∘
C)
Temp. at boil end (
∘
C)
Vol. for density (mL)
Mass of volume (g)
Density (g/mL)
Vol. for solubility (mL)
Vol. of water (mL)
Number of layers
Solubility
GOOD/POOR
GOOD/POOR
Explain the difference in solubility of your unknown in water compared to the other solvents.
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One of these liquids is used as a "blowing agent" in the manufacture of polystyrene foam because it is so volatile. Which liquid would you expect to be used as a
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Match the words in the left column to the appropriate blanks in the sentences on the right.
Reset
Help
Pentane
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Transfer the mixture into a separatory funnel and add 2 ml. more of bromine water and
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Procedure
The procedure[1] has been outlined below. Add details if needed so that you are able to complete the experiment in lab using only this document.
The following chemicals may be encountered during this experiment:
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- Part D One of these liquids is used as a "blowing agent" in the manufacture of polystyrene foam because it is so volatile. Which liquid would you expect to be used as a blowing agent? Match the words in the left column to the appropriate blanks in the sentences on the right. Reset Help Pentane is used as the "blowing agent" because it has a boiling point and is Ethylene glycol volatile low high Submit Request Answer < Return to Assignment Provide Feedback 6:16 PM O 4) 12/12/2021 amazon B. Mastering. Spotify Free 65°Farrow_forwardYou wash a separatory funnel with soap and water to ensure it is clean before extracting an aqueous solution with dicholormethane. You should take the time to make sure there are no drops of water left inside the separatory funnel. Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an answer. a True Falsearrow_forwardThe Background section of this lab explains why weight percent (%w/w) can be useful for comparing the relative amount of a desired or "active" compound in different products. During the lab, a major goal will be to decide which of your experiment flasks yield data that would allow you to correctly calculate the %w/w of sodium bicarbonate in these tablets. Let's assume that you correctly choose one flask for this calculation. If the amount of NaHCO3 in that flask was 2.70 g and the original weight of the tablet was 4.60 g, what is the %w/w NaHCO3 in the tablet that went into this flask? GIVE YOUR ANSWER TO TWO DECIMAL PLACES. Your Answer: Answerarrow_forward
- Please help do the brown sugar and white sugar separatelyarrow_forwardPART 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.arrow_forwardWhen you collected 50 mL of distillate in the collection flask, the mole percent of water in the distillation flask decreased to approximately 20 mole percent. 95 100 With your simple distillation set-up, what percentage of water will be in the vapor phase at this composition of the liquid? Read the theory page if you don't remember how to interpret the boiling point composition curve. a) 98 mole percent water b) 86 mole percent water c) 92 mole percent water d) 72 mole percent waterarrow_forward
- Draw the structure of 3-ethylhexane. Show all hydrogen atoms. Select Draw Rings More Erase about us careers privacy policy terms of use contact us help tv MacBook Air DII DD 12 F10 80 888 F9 F7 F8 F6 F5 F3 F4 F2 一 & delete %3D @ #3 $ 7 8 9. 3 4 Y U W E R return K .. .- 8:arrow_forwardPlease help with 1, 2 & 3arrow_forward19. What is thin layer chromatography (TLC) LEAST useful for from the list below? A) To determine if crystallization or distillation may be more effective for a separation B) To determine the number of components in a mixture C) To determine the appropriate solvent for column- chromatographic separation D) To monitor the progress of an organic synthesis reaction 14. The solubility of salicylic acid in water is 7.8g/100ml at 100°C and 0.25g/100ml at 25°. Estimate how much water is needed to recrystallize a 19g sample of salicylic acid? A) 150ml B) 250ml C) 300ml D) 400mlarrow_forward
- . Be sure to understand what the dilutionfactor is for each sample (dilution factor = the number used to determine the actualconcentration of the stock UK after the diluted samples are analyzed) ?arrow_forwardAnalysis of pure molecules either heterogenous mixture or analysis of pure molecules neither heterogenous mixture nor analysis of pure molecules heterogenous mixturearrow_forwardThe unknown organic substances which were critric acid, acetone, urea, beazaldehyda, glycerol, and MTBE was done in an experiment- use this to answer the questions. (Note: there was no boiling point or melting point done in this experiment however their reaction to NaHCO3 was done) a)Compare what you originally expected to identify at each step of the flow chart to what you identified. Were your predictions close to what you expected? Elaborate on your response. b)What was the biggest challenge you faced in differentiating between the functional groups? Were there any that were difficult to distinguish between? Why? b) Do you think this flow chart could be used to identify functional groups in a molecule that contains multiple different functional groups? Discuss. And how would you improve this flow chart procedure to better identify the organic compoun? (Flow Chart Below)arrow_forward
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