I have the results, calculations done, and the methods, I just need someone to write the introduction, discussion, and conclusion.
Extraction Lab Report
See the Lab Report Template for guidelines on formatting your Lab Report. Refer
to the information in this document for SPECIFIC topics to cover for this
experiment.
– Title
– Abstract
• Summary of the experiment (no experimental details such as masses, temperature, etc.)
• Objectives of the experiment (which technique was used and why)
• Results (% recovery, melting points)
– Introduction (information from the gapped notes)
• General acid-base reactions for the chemicals given (information from the gapped notes)
• Objectives again but in more detail (in the abstract they are just mentioned but not explained)
and why this is an important technique
• Change of solubility due to acid-base reactions
• Immiscible liquids
• Expected results (what does % recovery means, expected melting points)
– Experimental section
• Only the procedure you performed based on the sample you were assigned. Remember you are
writing to a chemist so don’t write unnecessary details
– Results
• Your acid-base solubility data
• Your extraction data: melting points (experimental and literature), calculations of percent
recovery (include all units)
• You also need a paragraph to explain/state your data (do not discuss it or relate to theory)
– Discussion (all discussion needs to be supported by theory, you will always be talking about your
specific experiment, with your own data and chemicals, but the explanation for it is based on theory)
• Purpose of the experiment again
• Discuss the difference in acid and base for benzoic acid and 4-ethyl aminobenzoate.
• Discuss the difference in polarity of the two chemicals in your mixture. (Non-polar, polar aprotic,
polar protic?)
• Discuss the change of solubility of the polar protic compound in terms of IMFs
• Discuss the immiscible liquids which were used in this experiment (why they don’t mix, how do
you know which one is the top and bottom layer out of the two solvents used during your
experiment)
• Discuss how extraction works based on difference in solubility of the specific compounds you
used and the polarity of the solvents used during the experiment.
• Discuss the acid-base chemistry performed on the polar protic compound during the extraction
and recovery steps (it doesn’t have to be in a lot of detail AND no arrow pushing is requested)
• Specific acid-base reactions for the mixture you separated. That means you need the 2 reactions
done in the lab.
• Discuss the percent recovery and melting points (was the experiment successful? What went
wrong, if something went wrong? How can it be improved?)
NOTE: If your experiment failed, it is preferred you talk about that, instead of getting somebody else’s
data. YOU WILL NOT GET POINTS DEDUCTED FOR BAD DATA, BUT YOU WILL LOSE POINTS FOR NOT
PROPER USE OR LACK OF THEORY. We want you to discuss and analyze your data, even if it is bad.
– Conclusion
• Summarize the experiment
• Objective of the experiment with the results
– References
ALL FIGURES, DIAGRAMS, AND SPECTRA SHOULD BE CLEAR AND EASY TO READ. ALL CALCULATION
EQUATIONS MUST BE CREATED BY YOU. See the Lab Report Template for information how to create
your own equations.
1
Copyright, Arizona State University
Arizona State University: Organic Chemistry Lab Experiment
Extraction Lab Package Separation and Purification
1. Background
• Extraction is used to extract one component from a chemical mixture based on different solubilities of
the components of the mixture in different solvents
• Schematic overview of how it works……
• The black and grey mixture both dissolve in solvent #1
• A solvent #2 is added that DOES NOT MIX with solvent #1
• The BLACK component in the mixture dissolves preferentially in solvent #2
• This can happen spontaneously, i.e. just on its own, HOWEVER, most often one of the components
(BLACK in this example) undergoes a chemical reaction to cause the differential solubility
• There are three chemical process we need to discuss in order to understand what is happening here
1. Immiscible liquids (liquids that do NOT mix) – intermolecular forces again!
2. Differences in solubility – intermolecular forces again AND a NEW IMF!
3. Chemical reaction – something new!
1.1 Immiscible Liquids : We already did this!
• We already know how to understand how and why two liquids would mix with each other or not in terms of
entropy and intermolecular forces (again!)
• When two liquids mix they dissolve each other, disorder and entropy increase. The IMFs in the two liquids
have to be broken as the molecules separate, and new IMFs form in the mixture.
Example: Liquid carbon tetrachloride and liquid hexane are miscible, that can be mixed in any ratio
and a single homogeneous liquid layer will form.
mixture in
solvent #1
solvent
#2
black EXTRACTED
from the mixture
INTO solvent #2
does NOT mix
with solvent #1
dissolves better in solvent #2
(often chemically altered)
solvent #1
add
solvent #2
work
2
The IMFs that are formed are similar to those that are broken when the liquids mix, the Thermal
Energy (RT) required for mixing is negligible, and, solution mixing is always favored by entropy.
Example: The solubility of liquid diethyl ether in liquid water (and vica versa), is small, neither are very
soluble in the other, these two liquids are immiscible.
Because the IMFs that are formed are weaker than those that are broken when the two liquids mix, the
thermal Energy (RT) required for mixing is large, and, even though mixing is favored by entropy, the two
liquids are immiscible and when mixed, form 2 layers.
For two immiscible liquids, which one is on top and which one is on the bottom?
• MOST organic liquids are less dense than water, USUALLY (but not always) the water will be the bottom
layer.
Cl
C
Cl
Cl Cl
Cl
C
Cl
Cl Cl
Cl
C
Cl
Cl Cl
+
carbon tetrachloride (liquid)
entropy INCREASES
when liquids mix
hexane (liquid)
Cl
C
Cl
Cl Cl
Cl
C
Cl
Cl Cl
mixture
moderate
induced dipole
(London dispersion)
moderate
induced dipole
(London dispersion)
NONPOLAR NONPOLAR
moderate
induced dipole
(London dispersion)
δ+δ-
O
moderate
energy COST to
BREAK THESE IMF
O
+
diethyl ether
O
H H
O
H H
HYDROGEN BONDING
LARGE energy COST to
break these IMF
water
dipole-dipole
MODERATE energy gain
when these are formed
O
H H
O
mixture
δ-
δ+dipole-dipole
IMF
δ-
δ+
δ-δ+ δ-
δ+
lower density
higher
density
density of diethyl ether = 0.73 g/cm3
density of H2O = 1.0 g/cm
3
H2O
O
3
1.2 Differential Solubility based on IONIC Intermolecular forces
• Ions dissolve (are soluble) in polar protic solvents, specifically in water, due to a new InterMolecular
Force: Ion-dipole
• Dissolving an organic ionic salt in water involves:
1) Breaking STRONG IONIC I.M.F. between the ions
2) Breaking STRONG H-bonding I.M.F. in the solvent
3) Gaining strong ion-dipole IMF in the solution
Entropy AND energy gain is sufficient to overcome the energy cost of breaking the I.M.F., therefore:
SALTS DISSOLVE IN WATER
• IONS tend NOT TO DISSOLVE in less polar ORGANIC SOLVENTS (e.g. hexane)
• Dissolving an organic salt in a NONPOLAR SOLVENT involves:
1) Breaking STRONG IONIC I.M.F. between the ions
2) Breaking WEAK I.M.F. in the solvent
3) GAINING WEAK induced-dipole I.M.F. in the solution
Energy gain is NOT SUFFICIENT to overcome entropy and the energy cost of breaking the I.M.F.:
SALTS do NOT DISSOLVE IN NONPOLAR SOLVENTS
1.3 Chemical Reactions that ALTER solubility: NEUTRAL > IONS and IONS > NEUTRAL
• A chemical reaction that changes a structure from NEUTRAL to IONIC will alter the solubility of that
compound, in WATER compared to ORGANIC SOLVENTS
• A simple chemical reaction that can be used in this way is an acid/base reaction, example: benzoic acid
• CONVERT FROM NEUTRAL TO IONIC, from water INSOLUBLE to water SOLUBLE (organic solvent
soluble to organic solvent insoluble)
ION-dipole
Me N
Me
Me
Me
O
H
H
Cl
O
HH
ION-dipole
H-bonding
VERY STRONG ion-dipole IMF in protic solvent
δ+δ+
δ− δ−
polar Protic solvent (H-bond)
ionic IMF
very strong
+
O
H H
O
H H
H-bonding
very strong
Me N
Me
Me
MeCl
larger
ENERGY GAIN
ENERGY GAIN
polar PROTIC
WEAK induced dipole
Me N
Me
Me
Me
Cl
ionic IMF
+
Me N
Me
Me
MeCl
larger
ENERGY COST
ENERGY COST
WEAK
induced dipole I.M.F.
NONPOLAR
WEAK induced dipole
O
O H
benzoic acid
ACID
O H+
Na
sodium hydroxide
BASE
O
O
O HNa
H
becomes
ionic
O
H
H
δ-
δ+ ion-dipole IMF
H-bonding
VERY strong
NEUTRAL
IONIC
ORGANIC SOLUBLE
WATER
SOLUBLE
4
• CONVERT FROM IONIC TO NEUTRAL, from water SOLUBLE to water INSOLUBLE (organic solvent
insoluble to organic solvent soluble)
• The theory of acid/base reactions will be covered in detail in lecture, what you need to know for now is not
how to predict acid/base reactions, but to understand how the bond forming and breaking processes in an
acid/base reaction can interchange neutral and ionic structure and how this changes solubility in organic
solvents and water
1.4 How an Extraction works that is based on Acid/Base Reactions
Here is an example of Extraction of an Acid, Extraction of a Base follows the same principles in the
reverse order
Extraction of benzoic Acid from a mixed solution of benzoic acid and naphthalene in an organic
solvent, e.g. diethyl ether.
Here we make use of the chemical reaction NEUTRAL > ION by deprotonating the acid with a base
• FIRST: Extract the benzoic acid from the mixed solution by ionizing it so that it dissolves in water.
• An aqueous solution of BASE (e.g. NaOH) is added, which deprotonates the acid producing the conjugate
base ionic form of the acid that then dissolves in the aqueous (water) layer
• SECOND: Now that the naphthalene and the benzoic acid are in two separate liquid layers, physically
separate the two liquids layers and then isolate the two chemicals from the two solutions.
O
O
BASE
O H+
ACID
O
O
benzoic acid
O H+
Na
H
H
H
Na Cl
H
becomes
neutral
+ Cl
salt
IONIC
NEUTRAL
WATER
SOLUBLE
ORGANIC SOLUBLE
shake!!+ Na+ –OH
H2O
organic
solvent
acid reacts with base
becomes ionized
is extracted into
the aqueous layer
CO2H
naphthalene
benzoic acid
organic
solvent
on top!
aqueous
(water)
layer
on bottom!
C
O
O
H
O HNa
O HNa
C
O
O Na
O HNa
EXTRACTED
into aqueous
phase as
ANION
organic
solvent
aqueous
(water) layer
5
• The organic solvent layer and the water are then PHYSICALLY separated, the aqueous layer is
REMOVED INTO a SEPARATE TUBE
• The organic solvent is evaporated to leave behind only the NAPHTHALENE SOLID
• Second, an aqueous acid is added to the water layer to REPROTONATE the BENZOIC ACID, making it
neutral
• The neutral acid does NOT dissolve in water, the solid acid precipitates, and it is separated from the water
by filtration
• In this way PURE SOLID NAPHTHALENE and PURE SOLID BENZOIC ACID are SEPARATED and
ISOLATED
There is not much video help on YouTube for this lab, but is shown separation of the two liquid layers in a
microscale conical bottom tube
2. What You Will Do
1. PRE-LAB: You must watch the online recitation, complete the GAPPED NOTES and also the
NOTEBOOK PRE-LAB notes as summarized below. EACH STUDENT must complete ALL OF THESE and
have them checked by the TA before you start the lab (not just one per group). These must be in your own
handwriting and words, you cannot type and paste into your gapped notes or notebook. Your handwriting
should be neat and legible. Everything in your notebook must be in black or blue INK (not pencil). All errors
or changes can be crossed out, initialed, and re-written. You will NOT BE ALLOWED TO PEFORM THE
LAB if you have not completed ALL OF THE PRE-LAB activities, including the Experiment and Objectives
worksheet, Section 4.
C
O
O Na
O HNa
C
O
O Na
O HNa
Aqueous
(water)
Layer
organic
solvent
aqueous
layer
apply
HEAT
EVAPORATE
(remove)
the solvent
pure
SOLID
naophthalane
SEPARATED and
ISOLATED!
C
O
OH
ClNa
add
ACID
H3O
+
convert from
ION > NEUTRAL
neutral
benzoic
acid
INSOLUBLE
in water
ClNa
pure
SOLID
benzoic acid
SEPARATED and
ISOLATED!
C
O
OH
aqueous
waste
FILTER!
Organic
diethyl ether
layer
6
2. IN LAB: Bring ALL PPE to lab (long pants, goggles, closed toe shoes), you will NOT be able to work in
the lab without these. TAKE CAREFUL NOTES in your notebook, EACH STUDENT will need to do this, not
one set of notes per group, have TA check and sign your notebook before leaving lab
3. POST-LAB: Complete the POST-LAB assignment. EACH STUDENT must turn in their OWN completed
PAPER COPY to their TA at the start of next lab INDIVIDUALLY (not one per group). Submit a lab report if
there is one associated with this particular lab (most labs do not have a lab report, check the syllabus).
2.1 Extraction of an organic acid from a mixture with another organic molecule
You will be given a mixture of Benzoic acid and naphthalene. The first part of the experiment is for you to
convince yourself that the acid has very different solubilities in different solvents depending upon its
ionization state.
Make a copy of the following table in your notebook and complete it with your observations when you
attempt to dissolve benzoic acid in an organic solvent (diethyl ether), in water and water
at high pH (with base). You will determine the pH conditions under which organic acids, i.e. benzoic acid,
and organic bases dissolve in water. For each entry in the table you will write soluble (if everything
dissolves) and insoluble (if nothing dissolves).
Solid diethyl ether
(organic solvent)
H2O NaOH 6M – pH ~ 14
Benzoic Acid (an
organic acid)
• In three clean test tubes, add a small quantity (the tip of a spatula, ~0.05g) of the organic acid benzoic
acid to each of them and label them.
• Add 0.5 mL of diethyl ether to one of the test tubes containing benzoic acid and shake it. Observe if
anything dissolves and record it in the solubility table.
• Add 0.5 mL of deionized H2O to one of the test tubes containing benzoic acid and shake it. The pH of this
solution will be close to neutral, roughly 7 or so. Observe if anything dissolves and record it in the solubility
table.
• Add 0.5 mL of 6M sodium hydroxide (NaOH) to one of the test tubes containing benzoic acid and shake it.
The pH of this solution will be high, around 14 or so. Observe if anything dissolves and record it in the
solubility table.
Write in your lab notebook as part of your in lab:
• Under which solvent conditions benzoic acid will dissolve
2.2 Extraction of an organic acid or base from a mixture: FIRST: dissolving the mixture in the
organic solvent.
• Weigh roughly 150 mg of the mixture of benzoic acid and naphthalene into a centrifuge tube. The mass
doesn’t have to be exactly 150 mg but be sure to record exactly how much YOU weighed.
7
• Add roughly 5 mL of diethyl ether to the centrifuge tube and gently shake until everything is dissolved. If
there is still a fine suspension, then add 1 more mL of diethyl ether and try again. Keep adding 1 mL of the
ether until everything has dissolved UP TO A MAXIMUM OF 8 mL. If all the material does not dissolve after
adding 8 mL, ignore the suspension and continue.
2.2.1 Extraction of an ORGANIC ACID using base
• Add 2 mL of the 3 M sodium hydroxide (NaOH) solution to the centrifuge tube. Gently shake to mix and
then cap the tube and make sure that the cap doesn’t leak. Shake more vigorously for just a couple of
seconds and then slowly unscrew the cap a little to release any pressure build up from evaporation of the
volatile ether. Tighten the cap again and then shake more vigorously again for just a couple of seconds and
release the cap again. Let the tube settle so that the organic and aqueous layers separate, and then extract
the lower water layer with a pipette and put in into a small clean beaker.
• Repeat this procedure with another 2 mL of the sodium hydroxide solution, shake and vent a couple of
times as before and then extract the water layer again into the same small beaker with a pipette.
• Add 1 mL of deionized water to the diethyl ether organic solution that is still in the centrifuge tube and
shake (with the cap on) to wash the ether to extract any remaining inorganic materials. Remove the water
layer and add it to the water solution in the beaker. Add another 1 mL of deionized water and wash again.
This time try to completely remove the water layer, and add it also to the water solution in the same beaker.
2 ml
NaOH
solution
in water
GENTLE
shake shake!
ether
layer
aqueous
layer
+
REMOVE LOWER
aqueous layer
ether solution aqueous solution
EXTRACT
2 ml
NaOH
solution
in water
GENTLE
shake shake!
ether
layer
aqueous
layer
+
REMOVE LOWER
aqueous layer
ether solution
SAME
beaker TWO
COMBINED
AQUEOUS
LAYERS
REPEAT
1 ml
WATER
shake!
REMOVE
add to
beaker
WASH
1 ml
WATER
shake!
REMOVE
add to
beaker
SAME
beaker
SAME
beaker
WASH
8
• A this point you should have the naphthalene in the diethyl ether solution in the centrifuge tube, and
separated from it, the anionic form of the organic acid as an aqueous ionic salt solution in the beaker.
2.2.2 Recovery of the organic acid from the water solution
• The organic acid needs to be returned to the neutral form so that it will precipitate out of the water solution
so that it can be isolated.
• Slowly and carefully, add 6M HCl solution DROP-BY-DROP with gentle shaking from a pipette to the
water solution until the pH reaches roughly 2.0. The solution needs to be quite acidic to ensure that the
organic acid is all in the protonated neutral form. As you add the acid you will start to see the solid organic
acid start to precipitate and the solution may become cloudy. This is the neutral acid coming out of solution.
• Set up a Hirsch funnel for filtration. Filter the water solution through the Hirsch funnel, scrape as many of
the benzoic acid crystals as possible into the filter funnel. Rinse the beaker with 1 mL of deionized water
and filter this also, trying to get as much of the solid as possible onto the filer paper. Leave the vacuum
running, pulling air through the filter paper for at least 10 minutes to dry your crystals.
• When they are as dry as possible, weigh your benzoic acid crystals, take a melting point and calculate the
percent recovery.
• You have now separated your acid by extraction in a high pH solution and re-precipitation in a low
pH solution.
2.3.3 Recovery of the non-polar compound from the diethyl ether solution
• The diethyl ether solution will still be wet because of the exposure to water, and so the solution needs to
be dried. Add small spatula ends full of sodium sulfate (drying agent) to the ether solution. Sodium sulfate is
a simple inorganic ionic solid that will absorb any water in the ether because the water is “attracted” to the
ionic solid due to the strong ion-dipole interactions.
+ C
O
O Nain diethyl
ether solvent
as an
aqueous
solution
C
O
O Na
6M HCl
in water
DROPWISE!
pH strip
6M HCl
in water
DROPWISE!
pH = 2.0!
vacuum vacuum
rinse 1mL
cold water
vacuum
C
O
OH
DRY weigh melting
point!
C
O
OH
9
• the sodium sulfate will not dissolve, but it may “clump” together as it gets wet with water. Keep adding
SMALL quantities of the sodium sulfate until it no longer clumps when added. Try to add the minimum
amount of the sodium sulfate.
• You now have to separate the solid sodium sulfate from the ether solution. Allow the solid to settle and
then carefully decant the ether solution into another clean beaker, pouring very slowly to avoid transferring
the solid sodium sulfate. Do not try to get all of the solvent at first, leave a little in the centrifuge tube with
the solid and then add 1 mL additional ether to the centrifuge tube with the solid and decant again. This way
you will wash most of the organics out of the centrifuge tube and leave as much of the sodium sulfate
behind as possible.
• Leave the beaker with the diethyl ether solution in the back of a fume hood close to a vent and allow the
ether to evaporate to dryness, OR, CAREFULLY blow a GENTLE stream if air with a pipette over the
solution to evaporate the solvent (be CAREFUL, the air stream can be strong when you first open the valve
and can blow your sample away), leaving naphthalene crystals behind.
• When they are as dry as possible, weigh your naphthalene crystals, take a melting point and calculate the
percent recovery.
2.4 Waste Disposal
• Discard used melting point tubes in a SHARPS CONTAINER!
• Dispose of unused organic chemicals (naphthalene, benzoic acid etc.) in the ORGANIC WASTE
CONTAINER in the back hood
• Dispose of aqueous samples in the acid or base waste containers as appropriate (CHECK pH FIRST!)
2.5 Troubleshooting the DigiMelt Machine
The Controls:
Box 1: Temperature Menu (e.g. Pushing start temp lets you control the starting
temperature.)
Box 2: Use these buttons to increase or decrease the settings.
Box 3: The Start/Stop buttons start or stop the machine depending on the status of
the melting point apparatus (preheating, ready, melting, or cooling).
• Set the start temp, ramp rate, and stop temperatures using the appropriate
temperature (Boxes 1 and 2) before pushing the start/stop button (Box 3).
• After you push the start/stop button, the machine will preheat to the starting temp
first. If the machine is too hot and your starting temp is lower than the current temperature of the machine,
the machine will need to cool to the desired starting temp first.
• Once the starting temperature has been reached, a green light will turn on, “Ready”. Push the start/stop
button again. When you are taking the melting point, the red light next to “Melt” must be lit.
• Once you are done measuring the melting point range, make sure to stop the machine by pushing the
start/stop button again. Make sure the machine is cooling down before you walk away from the machine.
2.6 Safety
Because this is a chemistry lab where you will be handling chemicals, accidents and contamination can
happen. It is important you wear your full PPE and be conscious about your cellphone use (which is not
DRY!
anhydrous
sodium
sulfate
CAREFULLY
decant!
CAREFULLY
evaporate
solvent!
in diethyl ether solvent
weigh melting
point!
10
allowed in the lab). Most lab injuries are caused by cross contamination with your gloves or splashes when
transferring solvents. Sometimes you don’t notice your gloves are contaminated and you touch your face or
handle your cellphone. Although we will constantly remind you of the proper use of PPE and lab safety
procedures, if and accident/injury/incident happens and you feel any irritation on your skin due to contact
with the chemicals used in this lab, you need to bring this to the attention of your TA immediately.
You will be using strong acid and base solutions, both of which could be hazardous if not used
carefully. Be sure to make sure that neither of these come into contact with your skin since both are
potentially corrosive and irritants and can permeate the skin. Be very careful to also avoid eye
contact (irritant, corrosive) and ingestion. Hydrochloric acid is also an inhalation hazard, avoid
breathing in the fumes.
Eye contact: Remove contact glasses and rinse eyes for at least 15 min in the eyewash while keeping your
eyes open. This can be very uncomfortable so ask for assistance to keep your eyes open and count the
time. Seek immediate medical attention.
Skin contact: Rinse for 15 min in the sink or eye wash (depending on the affected area) with soap in case
of serious skin contact and water. Remove any contaminated items of clothing and shoes. Seek immediate
medical attention.
Inhalation: Get fresh air. If you experience difficulty in breathing, then loosen your tie, belt, collar etc. Seek
immediate medical attention.
Ingestion: Rinse mouth thoroughly. Do NOT induce vomiting unless indicated by a medical personnel and
seek immediate medical attention.
It is very important to try to remain calm if an accident or injury happens and immediately inform the TA to
receive the appropriate care as needed.
3. Pre-Lab and In-Lab Notebook (10 pts)
3.1 General Lab Notebook Guidelines
A lab notebook is the standard way to organize, collect, and maintain data generated in lab. A well-kept lab notebook
should contain all of the information necessary for a third party to reproduce the experiment and corresponding data.
The lab notebook should be bound (a composition notebook works best) without perforated pages. A “spiral” lab
notebook is not acceptable, as the pages can be torn out easily.
The general guidelines for setting up your lab notebook are as follows:
• Page 1: Name; Course & Semester; Contact information (email)
• Page 2-3: Table of Contents
• Page 4 to the end: See the lab packet for each experiment for the details of what to include in the PRE-LAB
and IN LAB each week
Occasionally you will make a mistake while writing in a lab notebook. This is completely acceptable, science is messy
and you are learning. If you make a mistake, simply cross the mistake out with a single line (regardless of the size of
the error), initial the line, and date it. This lets everyone who reads the notebook know that you made a mistake and
that the piece of information is invalid. It is also important to use only a single line so that the original information can
still be read. Other things NOT to do in a lab notebook include:
• Adding or editing information after the lab period has ended.
• Writing in pencil.
• Scratching out information so it is no longer legible.
• Adding or removing pages.
• Using white out.
• Falsifying data.
Learning to organize and maintain a useful lab notebook is a skill that you will use in many scientific careers
11
3.2 Pre-Lab (5 pts)
You MUST have the following Pre-lab completed in your notebook and checked by the TA at the
beginning of lab! All parts of the Pre-lab must be handwritten IN INK. Include all of the following as part
of your pre-lab assignment:
1. Title and date of the experiment
2. Purpose of the experiment
3. Reaction (if applicable)
4. A completed version of the Table below. Look up the molecular structure, molecular weight, melting point
and MSDS information
Name Molecular
Structure
Molecular
Weight
(g/mol)
Melting Point
(◦C)
Density (g/cm3) MSDS (Hazards
Identification)
Naphthalene Not applicable
Benzoic Acid Not applicable
Sodium
Hydroxide
not applicable Not applicable
Diethyl ether Not applicable
Hydrochloric
Acid
not applicable Not applicable
The information you will need to complete this table is available from several websites, a good one is the
Sigma Aldrich website (www.sigmaaldrich.com). On the Sigma Aldrich site:
– Search for the compound
– The search will generate a list of different forms of the compound that the Sigma Aldrich sells.
– Choose the link for a pure form of the compound (not a solution, for example), and you should be able to
find the compound’s molecular structure, molecular weight, and melting point.
– Below the compound’s name, there should be a button “MSDS”. Click the button to get a pdf file of the
Materials Safety Data Sheet. Scroll to Section 2.2 of the document (“Hazards Identification”) and write
down the relevant information under “Hazard Statement(s)”.
5. Write in your notebook a response to the following SAFETY Questions
• What is the emergency procedure in case of skin contact with either the acid or base solution?
• What is the emergency procedure in case of inhalation of hydrochloric acid?
6. Complete the Table below using information in Section 2.2 of this packet
Waste Where to Discard
Organic Chemicals
Aqueous base waste
Aqueous acid waste
12
3.3 In Lab (5 pts)
IN LAB means the information you should be recording while you are IN lab each week. This will include:
• Quantities measured (volumes, weights, etc.)
• Observations (e.g. were there color changes? If appropriate, is the reaction refluxing properly? What
temperature is the reaction or the experiment? Is the apparatus leaking? How much time has
elapsed? Did a precipitate form?)
• All of the resulting data (e.g. melting point ranges, Rf values, IR spectral data)
• Percent Yield calculations (if applicable)
• Percent Recovery and any other calculations (if applicable)
• Important spectral data in a table (in case you lose the actual spectrum)
• Conclusions (Did the experiment work? Based on melting point, % recovery, yield, IR data, etc.)
• Anything that went wrong with the experiment
Everything written in your lab notebook must be legible and handwritten IN INK. The book should be
clean (no chemical spills etc.), should use correct notebook style, with mistakes crossed out with a line.
Have your notebook checked by your TA before you leave the lab!
13
4. Turn-in Pre-Lab Assignment – Experiment and Objectives (10 pts)
You MUST turn this paper in to your TA at the start of the LAB SESSION!
YOUR Name: ___________________________ Lab room: ________________
Partner Name: ___________________________ Lab time: _________________
TA Name: ____________________ Hood #: _________________
1. Give brief, 1- 2 sentence responses to the following questions:
(2 pts.) What two chemicals are in the mixtures you will be given to separate this week?
Naphthalene/benzoic acid
(1 pt.) In your extraction, the organic layer will mainly be the organic solvent, what organic solvent
will you use?
Diethyl ether
(1 pt.) The benzoic acid will be extracted into an aqueous layer. What liquid solvent will the aqueous
layer mainly consist of (any solution that consists mainly of this solvent is described as aqueous)?
water
(1 pts.) What is the name of the technique will you use to separate the mixtures this week?
Extraction
(2 pts.) In your extractions you will be using both an acid solution and a base solution. To extract an
acid from a mixture into an aqueous solution and then recover it from the aqueous solution, will you
add an acid solution in the first part to extract and then use base to recover the acid, or will you add
a base solution first followed by the acid solution?
base first, acid second
(1 pts.) During the extraction process, when you have both organic and aqueous solutions in
immiscible layers, will the naphthalene be in the aqueous or the organic layer?
Organic layer
(1 pts.) How will you recover the naphthalene from its solution at the end of the extraction?
Evaporate the solvent
(1 pts.) During the extraction procedure, will the organic layer be the top or the bottom layer?
Top layer
14
5. Extraction Post-Lab Assignment (20 pts.)
You MUST turn this paper in to your TA at the start of the NEXT LAB!
YOUR Name: ___________________________ Lab room: ________________
Partner Name: ___________________________ Lab time: _________________
TA Name: ____________________ Hood #: _________________
If you did not collect any data or are missing some data to complete this post-lab, then give your
source of data here and give a brief explanation why you have missing data. If you use your own
data you can go straight to question 1, no need to add anything here.
1. (1 pt.) Solubility Tests Results. Complete the table below based on your observations, an entry could be
“Insoluble” Sparingly soluble” “Quite soluble” or “Soluble”.
Chemical
Solubility in
diethyl ether
Solubility in
H2O
Solubility in
NaOH 6M
Benzoic Acid
2. (2 pts.) Extraction Recovery Efficiency
Chemical(s)
Weight (g)
Melting …
E xtra cti o n o f a n O rga ni c Ba se U si ng A ci d E xpe ri me nt
Da ni e lle Wi lde r
Pa rtne r: E ri c Si mo ne a u
TA : Du tta Su bha de e p
La b: T W Th, 10:00a m to 1:00pm
Ro o m: PSE 334
6/11/2018
A bstra ct:
The o ve ra ll go a l o f the e xtra cti o n la b i s to se pa ra te e i the r 4-e thy l a mi no be nzo a te fro m a
mi xtu re wi th na phtha le ne thro u gh u si ng the a ci d, hy dro ge n chlo ri de (HCl). I n o rde r to
de te rmi ne the i de nti ty o f the mi xtu re the di ffe re nce s i n so lu bi li ty a re u ti li ze d. Fu rthe r, the
me tho ds u se d i n the e xtra cti o n a re : i o ni za ti o n o f the ba se u si ng a ci d, phy si ca l se pa ra ti o n o f
the two fo llo wi ng so lve nts, a nd re co ve ry o f the ba se fro m the wa te r so lu ti o n. The ba se i s
the n pu ri fi e d thro u gh the pro ce ss o f re cry sta lli za ti o n. A s we ll, the so lve nt, na phtha le ne wa s
re co ve re d thro u gh e va po ra ti o n. Pu ri fi ca ti o n i s the n i de nti fi e d thro u gh the me lti ng po i nt o f
the re co ve re d ba se a nd so lve nt. The me lti ng po i nt o f na phtha le ne wa s 79.0-80o C, whi le the
me lti ng po i nt o f 4-e thy l a mi no be nzo a te wa s 87.0-87.7o C. The fi na l ca lcu la te d pe rce nt
re co ve ry fo r the e nti re mi xtu re wa s a bo u t 68.18%
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work
Introduction
The pu rpo se o f the e xpe ri me nt i s to u se e xtra cti o n to se pa ra te 4-e thy l a mi no be nzo a te a nd
Na phtha le ne . A n o rga ni c ba se , su ch a s 4-e thy l a mi no be nzo a te , ca n be e xtra cte d fro m a mi xtu re be ca u se
o f the di ffe ri ng so lu bi li ti e s o f the ba se a nd the re st o f the mi xtu re , whi ch be co me se pa ra te so lve nts by
wa y o f a che mi ca l re a cti o n. Ge ne ra lly , a Bro nste d a ci d o r ba se re a cti o n i s u se d be ca u se thi s i s a si mple r
wa y to ma ke a n o rga ni c ne u tra l co mpo u nd i nto a n i o ni c o ne tha t i s a lso so lu ble i n a qu e o u s e nvi ro nme nts
bu t no t o rga ni c o ne s. Wi th re ga rd to e xtra cti ng 4-e thy l a mi no be nzo a te , co mbi ne thi s wi th a n a ci d su ch
a s hy dro chlo ri c a ci d, wi th de pro to na te the ba se a nd cha se i t i nto i ts a ni o ni c fo rm, whi ch i s se e n i n the
fi rst e qu a ti o n. I n o rde r to re ve rse thi s o r o the rwi se pro to na te i t, a n a qu e o u s ba se mu st be a dde d to the
wa te r la y e r a s se e n i n E qu a ti o n 2.
1
(1)
(2)
Be co me s
i o ni c
4-e thy l a mi no be nzo a te Hy dro chlo ri c A ci d Sa lt fo rm 4-e thy l a mi no be nzo a te Wa te r
BASE ACID IONIC=WATERSOLUBLE
Sa lt So di u m Hy dro xi de 4-e thy l a mi no be nzo a te Wa te r So di u m Chlo ri de
IONICBASEBASEACID
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I mmi sci ble li qu i ds a re i nso lu ble wi thi n e a ch o the r be ca u se o f i nte rmo le cu la r fo rce s. Fo r two
su bsta nce s to be so lu ble wi thi n e a ch o the r, i nte r mo le cu la r fo rce s (I MFs) be twe e n the so lu te a nd the
so lve nt ne e d to be bro ke n a nd fo rme d; ho we ve r, ne i the r o f the se ha ppe n wi thi n i mmi sci ble li qu i ds
be ca u se e a ch li qu i d ha s di ffe re nt I MFs, mo st no ta bly tha t o f po la r a nd no npo la r i nte rmo le cu la r fo rce s.
Fo r e xa mple , si nce wa te r i s a po la r pro ti c su bsta nce , no npo la r su bsta nce s a re i mmi sci ble i n i t be ca u se i t
wo u ld ta ke a hi ghe r a mo u nt o f e ne rgy to bre a k the hy dro ge n bo nds tha n wo u ld be ga i ne d i n fo rmi ng
ne w I MFs whe n the so lu te wo u ld be di sso lve d. Whe n two i mmi sci ble so lve nts a re co mbi ne d, the y a re
phy si ca lly se pa ra te . Ge ne ra lly , the y fo rm a de nse a qu e o u s la y e r wi th a se pa ra te d o rga ni c la y e r o n to p o f
tha t.
Fo r thi s e xpe ri me nt, bo th la y e rs – a qu e o u s a nd o rga ni c – a re phy si ca lly se pa ra te d i n o rde r to
a llo w fo r e xtra cti o n o f the o rga ni c ba se . Thi s wi ll a llo w fo r the i so la ti o n a nd pu ri fi ca ti o n o f co mpo u nds i n
the mi xtu re . Mo re o ve r, i t wi ll a lso a llo w fo r the me a su ri ng o f the me lti ng po i nts, whi ch sho u ld be a bo u t
88.0-90.0°C fo r 4-e thy l be nzo a te a nd 79.5-81.0 fo r Na phtha le ne . A ddi ti o na lly , i n o rde r to o bta i n the
pe rce nt re co ve ry , the we i ght o f the pu re , e xtra cte d co mpo u nds wi ll be di vi de d by the sta rti ng to ta l
we i ght o f the mi xtu re a nd the n mu lti pli e d by 100. The pe rce nt re co ve ry sho u ld no t be e xa ctly 100%
be ca u se so me o f the co mpo u nds wi ll be lo st whe n the y a re be i ng e xtra cte d a nd re cry sta lli ze d. So me o f
the co mpo u nd wi ll be lo st bu t wi ll le a d to a co mpo u nd wi th gre a te r pu ri ty .
Experimental:
A cco rdi ng to the pro ce du re de scri be d i n the La b Pa cke t (A ri zo na Sta te U ni ve rsi ty , 2018), 154 mg o f 4-
e thy l a mi no be nzo a te /na phtha le ne a nd ro u ghly 5 mL o f di e thy l e the r we re a dde d to a ce ntri fu ge tu be
a nd sho o k u nti l the mi xtu re ha d di sso lve d. A fte r, 2 mL o f 3 M HCl wa s a dde d to the so lu ti o n, the
ce ntri fu ge tu be wa s ca ppe d a nd sho o k e a rne stly fo r a li ttle , the n u nca ppe d to re le a se a ny pre ssu re tha t
ha d bu i lt u p, a se co nd sha ke wa s pe rfo rme d be fo re le tti ng the tu be se ttle whi ch re su lte d i n the
2
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se pa ra ti o n o f the o rga ni c a nd a qu e o u s la y e rs, wi th the he lp o f a pi pe tte the bo tto m wa te r la y e r wa s
e xtra cte d a nd pu t i nto a sma ll be a ke r, thi s pro ce ss wa s re pe a te d a se co nd ti me , the wa te r la y e r wa s
e xtra cte d o nce a ga i n a nd a dde d to the be a ke r. Ne xt, the re ma i ni ng di e thy l e the r i n the tu be wa s
wa she d wi th a ro u nd 1 mL o f de i o ni ze d wa te r to co mple te ly e xtra ct the i no rga ni c ma te ri a ls o u t, the
wa te r so lu ti o n wa s re mo ve d a nd a dde d to the be a ke r a nd to a ssu re the pu ri ty o f the so lu ti o n the
pro ce ss wa s re pe a te d o ne mo re ti me . I n the e nd, thi s pro ce du re the di e thy l e the r so lu ti o n i n the
ce ntri fu ge tu be co nta i ne d na phtha le ne a nd the i o ni c fo rm o f the o rga ni c ba se a s a n a qu e o u s i o ni c sa lt i n
the be a ke r.
The i o ni c fo rm o f the o rga ni c ba se wa s re tu rne d to the de pro to na te d ne u tra l fo rm,
6M Na O H so lu ti o n wa s ca re fu lly a dde d dro p by dro p to the a qu e o u s so lu ti o n i n the be a ke r a nd wi th the
he lp o f the pi pe tte i t wa s li ghtly sti rre d u nti l the pH wa s clo se to 10.0, thi s wa s de te rmi ne d by pu tti ng a
dro p o f the so lu ti o n i n a pH stri p whi ch tu rne d blu e . A s the ba se wa s a dde d to the so lu ti o n the o rga ni c
ba se sli ghtly sta rte d to pre ci pi ta te , whi ch wa s the ne u tra l ba se co mi ng o u t o f the so lu ti o n. Ne xt, a Hi rsch
fu nne l wa s se t u p to a nd the so lu ti o n wa s a dde d to the fu nne l, to ge t a s mu ch so li d a s po ssi ble o u t o f
the be a ke r i t wa s ri nse d wi th 1 mL o f de i o ni ze d wa te r a nd pu t o n the fi lte r pa pe r tha t dra i ne d the wa te r
o u t, the o rga ni c ba se wa s re cry sta lli ze d 10 to 15 mi nu te s a fte r the va cu u m wa s le ft ru nni ng. The
cry sta ls we re ta ke n o u t o f the fu nne l a nd we i ghte d, cru she d a nd pu t o n a ca pi lla ry tu be a nd the me lti ng
po i nt wa s ta ke n.
The di e thy l e the r so lu ti o n tha t wa s sti ll we t, wa s dri e d by a ddi ng sma ll a mo u nts o f so di u m su lfa te to
the so lu ti o n whi ch a bso rbe d the wa te r tha nks to the stro ng i o n-di po le i nte ra cti o ns. The so di u m su lfa te
cru mple d to ge the r whi le a ddi ng the i no rga ni c i o ni c so li d, o nce no mo re clu mps we re fo rme d a ll the
wa te r wa s a bso rbe d, the so li d wa s a llo we d to se ttle a nd the n ca re fu lly wi th the he lp o f a pi pe tte the
e the r so lu ti o n wa s re mo ve d a nd pu t i nto a sma ll be a ke r, 1 mL o f di e thy l e the r wa s a dde d to the tu be to
3
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wa sh a nd a ssu re tha t mo st o f the na phtha le ne wa s re mo ve d a nd a dde d to the sma ll be a ke r. The be a ke r
wa s le ft to e va po ra te li vi ng na phtha le ne cry sta l be hi nd, whi ch we re we i ghte d, a nd the me lti ng po i nt wa s
ta ke n. A t the e nd, the pe rce nt re co ve ry o f 4-e thy l a mi no be nzo a te a nd na phtha le ne wa s a lso ta ke n.
Results
Ta ble 1 de pi cts the di ffe ri ng so lu bi li ti e s o f e i the r Be nzo i c a ci d o r 4-e thy l a mi no be nzo a te wi thi n
va ry i ng pH ra nge s.
Ta ble 1. A ci d/Ba se so lu bi li ty
SOLID/SOLVENT HCl6M–pH~0 H₂O NaOH6M–pH~14
BENZOICACID(AN
ORGANICACID)
I nso lu ble I nso lu ble So lu ble
4-ETHYL
AMINOBENZOATE(AN
ORGANICBASE)
So lu ble I nso lu ble I nso lu ble
The e xpe ri me nt be ga n wi th a 50/50 mi xtu re o f e xa ctly 154.0mg 4-e thy l a mi no be nzo a te
/na phtha le ne . A s we ll, the mi xtu re co nta i ne d a ppro xi ma te ly 5.0mL o f Di e thy l e the r. Ta ble 2 i nclu de s the
we i ghts o f e a ch co mpo u nd pre se nt a s we ll a s the me lti ng po i nts be fo re a nd a fte r e xtra cti o n o ccu rs.
Ta ble 2. I ni ti a l da ta a nd e xtra cti o n da ta
Compound Starting
Weight
(mg/mL)
Recovere
dweight
(mg)
Lit.
Melting
point
(°C)
Melting
pointafter
recovery(°C)
Percent
Recovery
4-ethyl
aminobenzoate/
154.0 mg n/a n/a n/a ∼68.18%
4
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Naphthalene
Diethylether 5.0 mL n/a n/a n/a n/a
4-ethyl
aminobenzoate
n/a 90.0 mg 88.0-
90.0°C
87.0 – 87.7°C ∼58.44%
Naphthalene n/a 15.0 mg 79.5-
81.0°C
79.0 – 80.0°C ∼9.74%
Pe rce nta ge re co ve ry o f the na phtha le ne , o rga ni c ba se , a nd the mi xtu re a s a who le a re gi ve n
u si ng E qu a ti o ns 3, 4, a nd 5 to ca lcu la te the m.
4−ethyl amino benzoate recovery=
90 mg of 4−ethyl amino benzoate recovery
154 mg4−e th y la mi n o b e nz o a t e /N a phth a l e n e
x 100=∼58.44
Naphtalene recovery=
15 mg of Naphthalene
154 mg 4−e th y l a m i n o b e nz o a t e / N a phtha le n e
x 100=∼9.74
Total Recovery=
9 0 mg 4−e th y la mi n o b e nz o a t e +15 mg N a phtha le n e
154 mg 4−e th y l a mi n o b e nz o a t e /N a phth a l e n e
x 100=∼68.18
Discussion:
The pu rpo se o f the e xpe ri me nt wa s to se pa ra te 4-e thy l a mi no be nzo a te o u t o f a 4-e thy l
a mi no be nzo a te /na phtha le ne mi xtu re fi rst di sso lve d i n a n o rga ni c so lve nt, di e thy l e the r, by co ndu cti ng
e xtra cti o n u si ng a n o rga ni c a ci d, hy dro chlo ri c a ci d, to cre a te a che mi ca l re a cti o n a nd de pro to na te the
o rga ni c ba se , thi s ca u se d the no w i o ni c co mpo u nd to be so lu ble i n wa te r so lu ti o n a nd i nso lu ble i n
a qu e o u s la y e rs, E qu a ti o n 1. Thi s pro ce ss fo rme d two la y e rs, a fte r the e xtra cti o n o f the a qu e o u s la y e r o u t
5
(3)
(4)
(5)
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o f the mi xtu re i nto a be a ke r the sa lt i s pro to na te d by a ddi ng a n a qu e o u s ba se , Na O H, the ne u tra l fo rm i s
ge ne ra te d o nce a ga i n, E qu a ti o n 2.
Be nzo i c a ci d wa s i nso lu ble i n lo w pH (a ci d) a nd wa te r, bu t i t wa s so lu ble i n hi gh pH (ba se ), whi le 4-
e thy l a mi no be nzo a te wa s so lu ble i n lo w pH (a ci d) a nd i nso lu ble i n wa te r a nd hi gh pH (a ci d), thi s
ha ppe ne d whe n the a ci d wa s a dde d to a ba se a de pro to na te d cre a ti ng a n i o ni c stru ctu re , ba se wo u ld be
a dde d to a n a ci d to de pro to na te d. The pu rpo se o f i de nti fy i ng the so lu bi li ty o f Be nzo i c a ci d a nd 4-e thy l
a mi no be nzo a te i n HCl, H2O , a nd Na O H wa s to fi nd o u t whi ch me tho ds ha d to be u se d a t the mo me nt
o f e xtra cti ng the o rga ni c co mpo u nd. The mi xtu re co nta i ne d 4-e thy l a mi no be nzo a te whi ch i s a
po la r pro ti c su bsta nce , pro ti c mo le cu le s ca n do na te a nd a cce pt H-bo ndi ng. Whi le Na phtha le ne i s a
no npo la r su bsta nce a nd ca nno t pa rti ci pa te i n the I nte rmo le cu la r fo rce s si nce i t ca nno t do na te o r a cce pt
H-bo ndi ng, whi ch me a ns tha t two su bsta nce s i n the mi xtu re do no t mi x a s li qu i ds.
6
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4-e thy l a mi no be nzo a te cha nge i ts so lu bi li ty whe n go i ng fro m ne u tra l to i o ni c, the ne u tra l
po la r pro ti c co mpo u nd wa s a ble to fo rm H-bo ndi ng whe n i o ni c i t ca n ma ke e ve n stro nge r i o n-di po le
i nte ra cti o ns, whi ch a llo ws i t to be wa te r so lu ble . The two i mmi sci ble li qu i ds i n thi s e xpe ri me nt a re
di e thy l e the r so lu ti o n a nd a qu e o u s i o ni c sa lt pro du ce d whe n the o rga ni c a ci d wa s a dde d to the mi xtu re .
Di e thy l e the r i s a n o rga ni c co mpo u nd whi le the i o ni c o rga ni c ba se i s a n a qu e o u s so lu ti o n, whi ch do no t
mi x tha nks to the di ffe re nce i n so lu bi li ty . The to p a nd bo tto m la y e rs a re de te rmi ne d the de nsi ty o f e a ch
so lve nt si nce the a qu e o u s so lu ti o n i s de nse r tha n the o rga ni c co mpo u nd, the a qu e o u s i o ni c sa lt so lu ti o n
i s a t the bo tto m.
The to ta l pe rce nt re co ve ry o f the 4-e thy l a mi no be nzo a te a nd Na phtha le ne wa s a ro u nd ∼45%. The
me lti ng po i nt ra nge o f 4-e thy l a mi no be nzo a te wa s ve ry bro a d a nd lo w, 82.5 – 89.9°C, whi ch i ndi ca te tha t
the o rga ni c ba se cry sta ls we re no t pu ri fy co mple te ly , i t co u ld ha ve co nta i ne d wa te r be ca u se i t wa s no t
dry e no u gh be fo re ta ki ng the me lti ng po i nt o r a ny o the r su bsta nce co u ld sti ll be i n the so lu ti o n be fo re
re cry sta lli za ti o n. I f the se , e xpe ri me nt i s re cre a te d i t i s ne ce ssa ry to pa y clo se a tte nti o n to the e xtra cti o n
pro ce ss a nd to le t dry the cry sta ls o f the o rga ni c co mpo u nd a s lo ng a s ne ce ssa ry de pe ndi ng o n ho w we t
the su bsta nce i s. Na phtha le ne ha d a me lti ng po i nt ra nge o f 79.3 – 80.8°C, whi ch i s a lmo st the sa me a s
the li te ra tu re me lti ng po i nt, thi s i ndi ca te s tha t the su bsta nce wa s pu ri fy .
Conclusion:
4-e thy l a mi no be nzo a te wa s e xtra cte d fro m a mi xtu re u si ng a nd a ci d, Hy dro chlo ri c a ci d. The
me lti ng po i nt ra nge o f 4-e thy l a mi no be nzo a te wa s 87.0– 87.7°C, a nd the me lti ng po i nt ra nge o f
Na phtha le ne wa s 79.0 – 80.0°C. The e xtra cti o n wa s a ble to pro du ce a to ta l pe rce nt re co ve ry o f a ro u nd
∼68.18%. The e xtra cti o n o f a n o rga ni c ba se u si ng a n a ci d wa s su cce ssfu l ba se d o n the re co ve ry o f e a ch
su bsta nce i n the mi xtu re .
7
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https://www.coursehero.com/file/31970491/Extraction-Lab-Report-2018-copydocx/
References
A ri zo na Sta te U ni ve rsi ty (2018, Ju ne 11). E xtra cti o n La b Pa cka ge .
Re tri e ve d fro m http://my a su co u se s.a su .e du /
E thy l 4-a mi no be nzo a te . (n.d.). Re tri e ve d Ju ne 11, 2018, fro m
https://www.si gma a ldri ch.co m/ca ta lo g/su bsta nce /e thy l4a mi no be nzo a te 165199409711?
la ng=e n(R)i o n=U S
Na phtha le ne . (n.d.). Re tri e ve d Ju ne 11, 2018, fro m
https://www.si gma a ldri ch.co m/ca ta lo g/su bsta nce /na phtha le ne 128179120311?
la ng=e n(R)i o n=U S
8
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Extraction Lab
Abstract
Introduction
Experimental
Results
Table 1. Benzoic acid and its solubility in different solutions.
Chemical
Solubility in diethyl ether
Solubility in H2O
Solubility in NaOH 6M
Benzoic Acid
Soluble
Insoluble
Soluble
Table 2. The weight, melting point, and literature melting point of starting mixture of benzoic acid and naphthalene, isolated naphthalene, isolated benzoic acid, and combined weight of isolated benzoic acid + naphthalene.
Chemical
Weight (g)
Melting Point ( C )
Literature Melting Point ( C )
Starting mixture of benzoic acid and naphthalene
0.153
N/A
N/A
isolated naphthalene
0.06
80.1-82.3
80
isolated benzoic acid
0.0294
121.1-122.8
121
combined weight of isolated benzoic acid + naphthalene
0.0594
N/A
N/A
Percent % Recovery:
Discussion
References
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