Daniel O Zamora Fischer Esterification 07/13/2020

Procedure for this lab is located on page 25

1. Safety Operating Procedures

a. C: Waste Disposal
b. D: Wearing Gloves
c. E: Acids and Bases
d. G: Using Organic Chemicals
e. H: Glassware
f. I: Heating Reactions

2. Hazard Analysis

a. Sulfuric Acid – Drop of acid on gloves, and head itches

i. Danger: Allows for acid to come to contact with skin and burn
ii. Avoid: Step away, remove gloves, then scratch
iii. What to do: Wash head for 15 min, seek medical attention.
b. Heating Reaction – Flask is cracked, remove goggles to wipe sweat from
forehead next to hotplate.
i. Danger: Boil/splashing into face area and burn face and eyes.
ii. Avoid: Don’t remove goggles close to bench, walk away from the bench if
needed.
iii. What to do: Use eye wash for 15 min.
c. Beaker of ethanol on edge of bench – Walking in lab with lab coat unbuttoned.
i. Danger: Spillage onto clothes that can get on to skin.
ii. Avoid: Button up the lab coat.
iii. What to do: Get rid of clothes, use shower.
d. Reaction in hood – Sash pulled all the way up
i. Danger: Proper extraction does not occur posing respiratory risks
ii. Avoid: Keep it down at all times
iii. What to do: Pull it down ASAP, notify the TA
Daniel O Zamora Fischer Esterification 07/13/2020

Methanol

CAS No. PS Color Odor FP BP MP d VP VD Sol

67-56-1 liquid colorless 11 64.6– -98 0.7914 97.25 1.11 soluble
alcohollike
64.7 @ 20

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure
Fire Severe fire hazard., vapors or gases may No flames, no sparks, Alcohol resistant foam,
ignite at distant ignition sources. no contact with hot carbon dioxide, regular
surfaces. dry chemical, water.

Inhalation Irritation, coughing, unsteady gait, Ventilation, local Remove from exposure
twitching, constipation, numbness and exhaust. immediately; get medical
shooting pains in the hands and attention.
forearms.

Skin Irritation, skin absorption may lead to Protective gloves and Remove contaminated
metabolic acidosis and effects on the clothing. clothes and jewelry,
eyes and central nervous system given thoroughly wash skin with
in acute ingestion. water.

Eyes Irritation, violent inflammation of the Safety goggles. Thoroughly wash eyes
conjunctiva, and epithelial defects on with water for several min,
the cornea. remove contact lenses if
possible, and seek medical
attention immediately.

Ingestion Inebriation, drowsiness, coughing, Do not eat or drink in If vomiting occurs keep
headache, dullness, weakness, vertigo, the laboratory. head lower than hips, get
dizziness, nausea, vomiting, medical attention, if
occasional diarrhea, and blindness. needed.

Carcinogenicity Not a known carcinogen. Mutagenicity Possible mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP = flash
point (°C); BP = boiling point (°C) @ 760 torr unless otherwise stated; MP = melting point
(°C); d = density or specific gravity (g/mL); VP = vapor pressure (torr) at specified
temperature (°C); VD = vapor density relative to air (1.0); Sol = solubility in water; N/A =
not available or not applicable.
Daniel O Zamora Fischer Esterification 07/13/2020

Methyl Benzoate

CAS No. PS Color Odor FP BP MP d VP VD Sol

93-58-3 liquid colorless fruity 82 198– -12 1.094 1 @ 39 4.68 0.016%
199

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure
Fire Moderate fire hazard., vapors or gases No flames, no sparks, Regular dry chemical,
may ignite at distant ignition sources. no contact with hot carbon dioxide, water,
surfaces. regular foam.
Inhalation Irritation, sore throat, and coughing. Ventilation, local Remove from exposure
exhaust. immediately; get medical
attention.
Skin Irritation. Protective gloves and Remove contaminated
clothing. clothes and jewelry,
thoroughly wash skin with
water.
Eyes Redness, pain, and irritation. Safety goggles. Thoroughly wash eyes
with water for several min,
remove contact lenses if
possible, and seek medical
attention immediately.
Ingestion Abdominal pain, vomiting, diarrhea, Do not eat or drink in If vomiting occurs, keep
and depression. the laboratory. head lower than hips; get
medical attention, if
needed.

Carcinogenicity Not a known carcinogen. Mutagenicity Not a known mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP = flash point
(°C); BP = boiling point (°C) @ 760 torr unless otherwise stated; MP = melting point (°C);
d = density or specific gravity (g/mL); VP = vapor pressure (torr) at specified temperature
(°C); VD = vapor density relative to air (1.0); Sol = solubility in water; N/A = not available
or not applicable.
Daniel O Zamora Fischer Esterification 07/13/2020

Sulfuric Acid Solutions

CAS No. PS Color Odor FP BP MP d VP VD Sol

7664-93-9 liquid colorless N/A N/A 100 N/A 1.84 1 <0.3 soluble

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure

Fire Negligible fire hazard., may ignite or Avoid contact Use extinguishing agents
explode on contact with combustible with combustible appropriate for
materials. materials surrounding fire.
Inhalation Ventilation, local Remove from exposure
Irritation, shallower and more rapid exhaust.
immediately, keep warm
breathing, sneezing, a burning or tickling
and at rest, get medical
sensation in the nose and throat, and cough.
attention immediately.
Skin Second and third degree skin burns, Protective gloves Remove contaminated
necrosis, charring, and shock. and clothing. clothes and jewelry,
thoroughly wash skin with
water, and get medical
attention immediately.
Eyes Burning or stinging sensation, lacrimation, Safety goggles. Thoroughly wash eyes
blurred vision, and conjunctival congestion. with water for several min,
remove contact lenses if
possible, seek medical
attention immediately, and
continue to wash eyes with
water.
Ingestion Burning pain in the mouth, throat, Do not eat or Contact physician
esophagus and abdomen, nausea, and drink in the immediately. Give water
vomiting. laboratory. or milk; if vomiting
occurs, keep head lower
than hips.

Carcinogenicity Known carcinogen . Mutagenicity Not a known mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP =
flash point (°C); BP = boiling point (°C) @ 760 torr unless otherwise stated; MP =
melting point (°C); d = density or specific gravity (g/mL); VP = vapor pressure (torr)
at specified temperature (°C); VD = vapor density relative to air (1.0); Sol = solubility
in water; N/A = not available or not applicable.
Daniel O Zamora Fischer Esterification 07/13/2020

Benzoic Acid

CAS No. PS Color Odor FP BP MP d VP VD Sol

65-85-0 solid white varying 121 249 122 1.2659 1 @ 96 4.2 2.9% @ 20
sharp @ 15

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure
Fire Slight fire hazard. Avoid heat, sparks, Regular dry chemical,
flames. carbon dioxide, water,
regular foam
Inhalation Irritation, sore throat, and coughing Ventilation, local Remove from exposure
exhaust. immediately, get medical
attention.
Skin Irritation and redness Protective gloves and Remove contaminated
clothing. clothes and jewelry,
thoroughly wash skin with
water.
Eyes Irritation and redness Safety goggles. Thoroughly wash eyes
with water for several
minutes, remove contact
lenses if possible, and
seek medical attention
immediately.
Ingestion Sore throat, gastric pain, nausea, Do not eat or drink in If vomiting occurs, keep
vomiting, and allergic reactions the laboratory. head lower than hips, get
medical attention, if
needed.

Carcinogenicity Not a known carcinogen. Mutagenicity Not a known mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP = flash point
(°C); BP = boiling point (°C) @ 760 torr unless otherwise stated; MP = melting point (°C);
d = density or specific gravity (g/mL); VP = vapor pressure (torr) at specified temperature
(°C); VD = vapor density relative to air (1.0); Sol = solubility in water; N/A = not available
or not applicable.
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Sodium Sulfate

CAS No. PS Color Odor FP BP MP d VP VD Sol

7757-82-6 crystals, white odorless N/A N/A 884 2.671 N/A N/A 17% @ 20
powder

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure

Fire Negligible fire hazard. N/A Use extinguishing agents

appropriate for
surrounding fire.
Inhalation Irritation. Ventilation, local Remove from exposure
exhaust. immediately; get medical
attention.
Skin Irritation. Protective gloves and Remove contaminated
clothing. clothes and jewelry,
thoroughly wash skin with
water.
Eyes Irritation. Safety goggles. Thoroughly wash eyes
with water for several
min, remove contact
lenses if possible, and
seek medical attention
immediately.
Ingestion Diarrhea, fluid loss, blood in stools, and Do not eat or drink in Contact physician
hypotension. the laboratory. immediately. If vomiting
occurs, keep head lower
than hips.

Carcinogenicity Known carcinogen . Mutagenicity Known mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP =
flash point (°C); BP = boiling point (°C) @ 760 torr unless otherwise stated; MP =
melting point (°C); d = density or specific gravity (g/mL); VP = vapor pressure (torr)
at specified temperature (°C); VD = vapor density relative to air (1.0); Sol = solubility
in water; N/A = not available or not applicable.
Daniel O Zamora Fischer Esterification 07/13/2020

Sodium Chloride

CAS No. PS Color Odor FP BP MP d VP VD Sol

7647-14-5 crystalline colorless odorless N/A 1413 801 2.165 N/A N/A 35.7% @ 0
powde to white

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure
Fire Negligible fire hazard. N/A Use extinguishing agents
appropriate for
surrounding fire.
Inhalation Coughing, dryness, and sore throat. Ventilation, local Remove from exposure
exhaust. immediately, get medical
attention.
Skin Irritation Protective gloves Remove contaminated
and clothing. clothes and jewelry,
thoroughly wash skin with
water.
Eyes Redness, pain, irritation and a stinging Safety goggles. Thoroughly wash eyes
sensation with water for several
min, remove contact
lenses if possible, and
seek medical attention.
Ingestion Dryness of mucous membranes, a violent Do not eat or If vomiting occurs, keep
inflammatory reaction in the drink in the head lower than hips; get
gastrointestinal tract, and ulceration if very laboratory. medical attention, if
large doses are taken. needed.

Carcinogenicity Not a known carcinogen. Mutagenicity Not a known mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP = flash point (°C);
BP = boiling point (°C) @ 760 torr unless otherwise stated; MP = melting point (°C); d = density or
specific gravity (g/mL); VP = vapor pressure (torr) at specified temperature (°C); VD = vapor density
relative to air (1.0); Sol = solubility in water; N/A = not available or not applicable.
Daniel O Zamora Fischer Esterification 07/13/2020

Sodium Carbonate

CAS No. PS Color Odor FP BP MP d VP VD Sol

497-19-8 colorless odorless N/A decomposes 851 2.536 N/A N/A 7.1% @ 0
crystalline to white
powder,
crystals

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure
Fire Negligible fire hazard. N/A Use extinguishing
agents appropriate for
surrounding fire.
Inhalation Irritation, coughing, and shortness of Ventilation, local Remove from exposure
breath. exhaust. immediately; get medical
attention.
Skin Irritation and redness Protective gloves Remove contaminated
and clothing. clothes and jewelry,
thoroughly wash skin
with water.
Eyes Severe irritation, redness, pain, and Safety goggles. Thoroughly wash eyes
blurred vision with water for several
min, remove contact
lenses if possible, seek
medical attention
immediately, continue to
wash eyes with water.
Ingestion Corrosion of the gastric mucosa, sore Do not eat or drink Contact physician
throat, gastrointestinal disturbances, in the laboratory. immediately. Give
nausea, vomiting, abdominal pain, and water or milk; if
diarrhea. vomiting occurs, keep
head lower than hips.

Carcinogenicity Not a known carcinogen. Mutagenicity Not a known mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP = flash point (°C);
BP = boiling point (°C) @ 760 torr unless otherwise stated; MP = melting point (°C); d = density or
specific gravity (g/mL); VP = vapor pressure (torr) at specified temperature (°C); VD = vapor density
relative to air (1.0); Sol = solubility in water; N/A = not available or not applicable.
Daniel O Zamora Fischer Esterification 07/13/2020

Diethyl Ether

CAS No. PS Color Odor FP BP MP d VP VD Sol

60-29-7 liquid colorless sweet -40 35 -116 0.7 442 @ 2.6 6.9%
20

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure
Fire Severe fire hazard., severe explosion No flames, no sparks, Alcohol resistant foam,
hazard, may form explosive peroxides, no contact with hot carbon dioxide, regular dry
vapors or gases may ignite at distant surfaces. chemical.
ignition sources.
Inhalation Central nervous system depression Ventilation, local Remove from exposure
with drowsiness, dizziness, nausea, exhaust. immediately; get medical
headache, and lowering of the pulse attention.
and body temperature.
Skin Irritation, defatting, and drying of the Protective gloves and Remove contaminated
skin. clothing. clothes and jewelry,
thoroughly wash skin with
water.
Eyes Painful inflammation. Safety goggles. Thoroughly wash eyes
with water for several min,
remove contact lenses if
possible, and seek medical
attention immediately.
Ingestion Central nervous system depression Do not eat or drink in Contact physician
with nausea, vomiting, drowsiness, the laboratory. immediately.
dizziness; stomach may become
promptly distended, which may hinder
breathing

Carcinogenicity Not a known carcinogen. Mutagenicity Possible mutagen.

For more detailed information consult the Material Safety Data Sheet for this compound.

Abbreviations: CAS No. = Chemical Abstracts Service Registry Number; PS = physical state; FP = flash point
(°C); BP = boiling point (°C) @ 760 torr unless otherwise stated; MP = melting point (°C);
d = density or specific gravity (g/mL); VP = vapor pressure (torr) at specified temperature
(°C); VD = vapor density relative to air (1.0); Sol = solubility in water; N/A = not available
or not applicable.
Daniel O Zamora Fischer Esterification 07/13/2020

3. Quest

4. Purpose

The purpose for this experiment was to use and observe the Fischer esterification
reaction. This will involve converting benzoic acid into methyl benzoate. This will be
accomplished by using Fischer esterification in order to turn the OH group with OMe.
Afterwards, an IR will be taken to be able to observe how the reaction performed
changed the molecules along with a GC chromatogram. These will be able to be used to
confirm identity which will be a first without relying on the melting point.

5. Data and Results

Mass of Product: 0.213 g

mols
molatiy=
liters
.003 L∗1 M of Benzoic acid=.003 mols
Molecular Weight=122.12 g / mol
g
122.12 ∗.003 mol=.366
mol
experimental yield .213
Percent Yield= ∗100= ∗100=58.2
actual yield .366
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6. Data and Results Analysis

The retention time for the product of interest, methyl benzoate was 1.304 minutes. The
known retention time for this molecule is 1.27 minutes indicating that the value of the
of the two. Are extremely closes. However there seems to be some error. The likelihood
Daniel O Zamora Fischer Esterification 07/13/2020

here is likely that there could’ve been some slight error in the machine since the time
differences mount to 1.8 seconds an error small enough that it can be argued that is
almost identical to the known number. Nothing appears to be odd with the peak shape
in fact the most notable thing could be that the response is very low which might’ve
been because of the sheer size of a response obtained from the solvent but aside from
that nothing appeared to be out of the ordinary.

The percent yield for this reaction was 58.2%. Part of the reason that this yield is low is
because this reaction works in a state of equilibrium. Since the reaction normally
operates in a 4 to 1 ratio in favor of the reactants there will always be some left over.
Adding more benzoic acid would work to push the reaction to produce more product
but consequently become less effective as more is added and end up with a skewed
amount being produced that it looks like it was insufficient. Something that can be done
to improve the yield is determine how much of the product was intended to be made
but without an accurate measurement of the other reactants this will be hard to
measure.

The IR looked great. The functional group showed the loss of the hydroxyl group peak
replaced with the peak of OMe meaning that the peaks that were meant to be present
are present and those that are not are not for this region. When comparing it to the
known IR it shows that nothing is on the IR that shouldn’t be and that no peaks are
missing. The same thing can be said for the finger printing region. Although there were
slight differences on how the experimental IR and the known IR looked when compared
all the peaks that were expected were there indicating that this error came from when
the background was taken. As previously mentioned all the peaks that were expected
were there, none were lost absent, leading to the conclusion that no reactions occurred,
aside from the intend one, to cause changes to the fingerprinting region. This leads to
the conclusion, with a match score of 95.05% that the intended product was created,
and the hydroxyl group was replaced with the OMe group.

7. Discussion

For this reaction it begins with the protonation of carbonyl by acid, in this case H 2SO4
causing the oxygen on the carbonyl to get aa positive charge and become more
electrophilic. This allows for the oxygen in the carbonyl to attack the electrons in one of
its double bonds to carbon over to itself into a lone pair. This however would leave
carbon with three bonds causing to be electrophilic itself. At this point the group we are
attempting to add, MeOH, acts like a nucleophile and donates one of the electron pairs
to form a bond with the carbon. This however leads to the issue of the oxygen atom
now having a positive charge. What occurs is a proton transfer to a neighboring hydroxyl
group that transfers one off the hydrogens of our original MeOH allowing the hydrogen
to become positively charged. On the idea that the oxygen beings to pull on the
electrons, this time it attempts to pull over the electron that happen to bond it to
carbon. At this point the pervious carbonyl group donates one of its lone pairs to reform
Daniel O Zamora Fischer Esterification 07/13/2020

a double bond. This provides the opportunity to allow the nucleophilic oxygen to pull
out the electrons in the bond over onto itself and for water. Finally, for completion of
this reaction in order to deal with the positive oxygen on the carbonyl the floating HSO 4-
will act as a base and form a bond to the hydrogen on the carbonyl group, allowing the
electrophilic oxygen to pull out the electrons from the bond it had to hydrogen onto
itself into a lone pair.

Figure 1: The reaction mechanism drawn to visually show what is occurring.

8. Conclusion

The results for this experiment were that .213 g was the amount of product that was
produced. This yielded a percent yield of 58.7 %. The IR, as was previously discussed,
produced data that indicated that the functional group of the molecule was successfully
changed to OMe but that the fingerprint region stayed the same. Since the graph was a
95.05% match to the saved graph for this product it was reasonable to assume that the
product was successfully synthesized. Another method to confirm the identity of the
product, that was used, is through the GC chromatogram. Here there was a retention
time of 1.304 minutes which was only off by 1.8 seconds.