Standard Operating Procedures

Daniel O Zamora 9-Fluorenone Reduction 07/13/2020
Procedure for this lab is on page 23 of the lab notebook.
1. Standard 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. Methanol: Using a hotplate with exposed wires
i. Danger: Possible ignition/electrocution
ii. Avoid: Keep liquid away from outlet/machine; report to TA over danger
iii. What to do: Extinguish if ignited inquire to TA over how to handle
situation
b. Sodium Borohydride: Accidental spill onto exposed hand
i. Danger: Irritation and damage to skin
ii. Avoid: Wear gloves
iii. What to do: Wash hands for 15 min, seek medical attention if necessary
c. 9-fluorenone: Accidental ingestion
i. Danger: Can be harmful, induce nausea, vomiting
ii. Avoid: Do not eat inside the lab
iii. What to do: Seek medical attention
d. Beaker: Chipped top
i. Danger: Can present a cutting hazard, spillage
ii. Avoid: Inform TA to replace equipment
iii. What to do: Empty contents, handle with care. Report to TA. Seek
medical attention if necessary
Ac e topheno ne
CAS No . PS Co lo r Odo r FP BP MP d VP VD Sol

1 @
98-86-2 liquid colorless floral 82 203 19-20 1.030 4.14 0.55% @ 20
15
Type s o f Ac ute Hazards /S ympto ms Pre ve ntio n Firs t Aid/Fire

Hazard/Expo s ure
Fire Moderate fire hazard. Regular dry
No flames, no
chemical, carbon
sparks, no contact
dioxide, water,
with hot surfaces.
regular foam
Inhalatio n Irritation, coughing and central Ventilation, local Remove from exposure
nervous system depression with exhaust. immediately, get
headache, dizziness, and narcosis. medical attention.
S kin Irritation, redness, pain, and mild Protective gloves Remove contaminated
burns. and clothing. clothes and jewelry,
thoroughly wash skin
with water.
Eye s Severe reaction with only transient Safety goggles. Thoroughly wash eyes
optical irregularity of the corneal with water for several
epithelium. min, remove contact
lenses if possible, and
seek medical attention
immediately.
Ing e s tio n Sore throat, abdominal pain, Do not eat or drink in Contact physician
nausea and central nervous system the laboratory. immediately. If
depression with headache, vomiting occurs, keep
dizziness, and narcosis. head lower than hips.
Carc ino g e nic ity Not a known carcinogen. Mutag e nic ity 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.
Ethanol

64-17-5 liquid colorless alcoholic 13 78 N/A 0.7893 40 1.59 soluble
torr
@ 19

Hazard/Expo s ure
Fire S e ve re fire hazard., vapors or No flames, no Alcohol resistant foam,
gases may ignite at distant ignition sparks, no contact carbon dioxide, regular
sources. with hot surfaces. dry chemical, water
Inhalatio n Irritation, central nervous system Ventilation, local Remove from exposure
depression with headache, stupor, exhaust. immediately; get
fatigue, dizziness, drowsiness, medical attention.
dullness, lassitude, and loss of
appetite may occur.
S kin Redness, burning, contact Protective gloves Remove contaminated
dermatitis, skin absorption may and clothing. clothes and jewelry,
occur. thoroughly wash skin
with water.
Eye s Immediate burning, stinging, reflex Safety goggles. Thoroughly wash eyes
closure of the lids, tearing, and with water for several
temporary injury of the corneal min, remove contact
epithelium. lenses if possible, and
immediately.
Ing e s tio n Emotional lability, decreased Do not eat or drink in If vomiting occurs, keep
inhibitions, exhilaration, the laboratory. head lower than hips;
boastfulness, belligerency, visual get medical attention, if
impairment, muscular needed.
incoordination, sensory
disturbances, dilated pupils, rapid
pulse, nausea, vomiting, sweating,
drowsiness, and stupor.
Carc ino g e nic ity Not a known carcinogen. Mutag e nic ity Possible mutagen.
trans -p -Anis alac e to phe no ne
CAS PS Co lo r Odo r FP BP MP d VP VD Sol

No .
959-33- solid yellow N/A N/A N/A 73–76 N/A N/A N/A insoluble
1

Hazard/Expo s ure
Fire Flammable. Emits toxic fumes Avoid heat, sparks, Water spray, carbon
under fire conditions. flames. dioxide, dry chemical
powder or appropriate
foam.
Inhalatio n Irritant, may be harmful if inhaled. Ventilation, local Remove to fresh air. If
exhaust. breathing is difficult,
give oxygen.
S kin Irritant, may be harmful to the skin. Protective gloves Immediately flush skin
and clothing. with soap and copious
amounts of water for at
least 15 minutes.
Remove contaminated
clothing.
Eye s Vapor or mist is irritating to the eyes, Safety goggles. Immediately flush eyes
may be harmful. with copious amounts of
water lifting upper and
lower lids often. Seek
medical advise.
Ing e s tio n May be harmful if swallowed. Do not eat or drink in If swallowed wash out
the laboratory. mouth with water. Call
a physician.
temperature (°C); VD = vapor density (g/mL); Sol = solubility in water; N/A = not available
or not applicable.
p-Anis alde hyde

123-11-5 liquid colorless floral 116 118– -1 1.119– 133.5 4.7 slightly
121 1.123 @ 73 soluble

Hazard/Expo s ure
Fire Slight fire hazard. Avoid heat, flames, Regular dry chemical,
sparks carbon dioxide, water,
regular foam.
Inhalatio n N/A Ventilation, local Remove from exposure
exhaust. immediately; get
medical attention.
S kin Irritation. Protective gloves Remove contaminated
and clothing. clothes and jewelry,
with water.
Eye s N/A Safety goggles. Thoroughly wash eyes
with water for several
min, remove contact
lenses if possible, and
immediately.
Ing e s tio n Do not eat or drink in If vomiting occurs, keep
the laboratory. head lower than hips;
get medical attention, if
needed.
S o dium Hydroxide
CAS No . PS Co lo r Odo r FP BP MP d VP VD So l
1310-73- solid white odorless N/A 1390 318 2.130 100 >1 soluble
2 @
1111

Hazard/Expo s ure
Fire Negligible fire hazard. N/A Use extinguishing
agents appropriate for
surrounding fire.
Inhalatio n Irritation, sore throat, burning Ventilation, local Remove from exposure
sensation, laryngitis, coughing, exhaust. immediately, keep warm
destruction of mucous membranes, and at rest; get medical
headache, nausea, vomiting, and attention immediately.
delayed pulmonary edema.
S kin Redness, cutaneous burns, and Protective gloves Remove contaminated
skin fissures. and clothing. clothes and jewelry,
with water, get medical
attention immediately.
Eye s Disintegration and sloughing of Safety goggles. Thoroughly wash eyes
conjunctival and corneal with water for several
epithelium, corneal opacification, min, remove contact
edema, ulceration, and blindness. lenses if possible, seek
medical attention,
continue to wash eyes
with water.
Ing e s tio n Corrosion of the lips, mouth, Do not eat or drink in Contact physician
tongue and pharynx, severe the laboratory. immediately. Give
esophageal and abdominal pain, water or milk; if
and vomiting. vomiting occurs, keep
head lower than hips.
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.
3. Quest
4. Purpose
The purpose of this experiment is to be able to learn a reaction that involves conversion
of ketone to a secondary alcohol. The main mechanism will be to use the electrophilic
nature of the carbon atom involved in the double bond. For this specific reaction NaBH 4
will be used which means its specific properties will be exemplified in the reaction
mechanism. After it is produced, the melting point will be taken to confirm the identity
of the final product. An IR will also be used to be able to determine any changes in the
different regions of the molecule.
5. Data and Results
Mass Product Obtained: 0.065 g

actuaal yield
Percent yield= ∗100
theoretical yield
.065
∗100=65 %
.1
MP: 150 - 153 °C
6. Data and Results Analysis
The percent yield for fluorenol product in this experiment was 65%. These results were
mostly likely because normally more time is afforded to these reactions to be able to
reach completion under heat but due to time constraints it had to be cut short. Another
thing that needs to be kept in mind is that outside from the real-world reactions are
susceptible to side reactions, in this case acid reaction with MeOH, and other factors
that hinder the ability to be able to reach ideal or theoretical yields. With that in mind, I
can’t think of anything that could’ve been done to improve this experiment following
the same procedure. Changing the procedure, I would’ve allowed for more time under
heat that would allow the reaction to proceed to completion.
The melting point often tells us what the product we are working with is. In this case we
got a range of 150-153 °C the safety data sheets for the expected product, 9-Fluorenol,
indicate that the range for the melting point for this substance is 152-158 °C. This tells
us two things, most of the product that was synthesized is 9-Fluorenol since our starting
compound, 9-Fluorenone, had its own melting point range at 80-83 °C. The next thing is
that since the value is lower and our range actually goes below the known range it is a
high indication that there are some impurities with the final product. This is a likely
indication that there was an error present in the steps where of the experiment that
involved the crystallization of the product after having neutralized it water. The cause of
this was likely cause of this could’ve been some difficulties during the process of trying
to get both beakers warm. Since there’s a huge discrepancy in the volumes and the type
of substances each beaker contained, I should’ve warmed the beaker with the water
first to have avoid the difficulties I ran into. If so, it is likely that the final product
would’ve been of less volume but have a more accurate melting point.
The IR shows interesting data. The functional group, in this case the hydroxyl group, is
not expected to be strong or highly defined curves when in solid form. Therefore,
theoretically at least a bump should be expected from the OH group. The curve for the
oxygen group that would’ve been expected from the initial compound should disappear
and not be noticeable and judging by what seems to be the absences of any unwanted
peaks it is reasonable to assume that the curve for the oxygen in the original compound
is missing. Other than that, it seems that in the sample oof the final product all the
original oxygen functional group had been turned into a hydroxy functional group. The
IR fingerprint region was identical to the expected outcome. No peaks were present that
shouldn’t have been, and none were missing. This is an indication that the rest of the
structure of the molecule went unchanged when it underwent reaction. This means that
the rest of the bonds in the molecule were identical, the benzene rings and all,
indicating that this region of the molecule has not changed. Overall, the IR strongly
supports that 9-fluorenol was synthesized. Aside from matching the expected peaks in
the IR graph the instrument itself matched the graph to 9-flourenone and gave about a
92% match to the expected graph. There did seem to be shifting that could indicate that
there was an error when the background was performed or could be explained by the
unexpected peak at the 650 cm-1.
7. Discussion
The reaction for this mechanism involves using sodium borohydride in order to turn the
oxygen in 9-Flourenone to turn it into a hydroxyl group. Once in solution the ionic bonds
in the sodium borohydride break apart and this leaves the borohydride with a partial
negative charge due to the extra hydrogen bond that is bonded. This make the bromine
atom in the disassociated structure to be nucleophilic allowing it to donate the
hydrogen, and the electrons associated with the bond, to transfer over to the carbon
atom that is doubly bonded to an oxygen atom. Since the carbon atom can only handle
four bonds at a time the, and the oxygen exhibits greater electrophilic properties, the
electrons of one of the bonds that form the double bond transfer over to the oxygen
simultaneously while the carbon accepts the hydrogen atom and the electrons that
come with it. The positively charged sodium ion stabilizes the oxygen atom which, at
this point, has acquired a negative charge in solution. At this point when acid is added a
hydrogen cation is dissociated into solution due to the methanol basic properties which
then forms a bond with the negatively charged oxygen atom forming the hydroxyl group
and completing the successful synthesis of 9-flourenone to 9-fluorenol. The acid also
quenches any of the remaining sodium borohydride from the solution.
Figure 1: The drawn reaction for the reduction of 9-Flourenone.
This experiment required a specific set up in terms of glassware. Since the reaction
requires heat to be able to be initiated at the stage, since that will be the main driving
source of energy to get the reaction started and ensure that everything in solution can
dissolve, a condenser will be needed to avoid the evaporation of the solvent. The
condenser itself is set up to allow cold water from come from the bottom/lower
portions off the glassware and the steady stream push up warmer water through the
higher end. This allows for any initial vapor that is formed through the heating to rise
through the cooler portion of the condenser and then experience condensation and
cooling effect. This will help prevent a large amount of solvent lost but also minimize the
amount of boiling that will be taking place in the reaction. Two different temperatures
are giving in this experiment after an initial 15 minutes at 300 °C and then 150 °C at
another 15-minute interval. This is to provide enough energy necessary to allow for the
reaction to progress but also prevent a scenario where there is overheating, and solvent
is evaporated and loss at a faster rate than can be cooled down by the condenser. When
ice was added, this allowed for the solution to cool down causing something to
precipitate. This was a result because 9-Flourenol does not form hydrogen bonds as well
as 9-Flurouene, so although it is dissolved at the high temperature that it was originally
heated the addition of ice forces its precipitation. After the addition of ice there was
initial rinsing of the product that involved wash with DI water, this was to be able to
neutralize any remaining acid that might have been left on the product. Finally, because
an IR is needed of the product, the precipitate was then re-heated and dissolved in
solution. Then it is again forced to precipitate, and water is then added to the point
where precipitate is at the point of forming and then methanol is added to allow for the
final crystallization of the product. After all these processes the product should’ve been
purified from any contaminants, or at least most of them. At this point the product can
then be left to dry, taken the melting point of, and taken an IR of.
8. Conclusion
The percent yield for this reaction was 65% with .065 g off product. The most likely error
from this reaction was due to the fact that the reaction was not left under the presence
of heated for a longer time. The issue of not all reactions being able to reach theoretical
efficiency likely played a part but was probably not the main source of error. The
melting point that was measured gave a range of 150 - 153 °C a 3-degree range. This
indicated that there were minor impurities with the final product that were obtained
that arose after complications with the purification and crystallization part of this
procedure. Finally, the IR showed that the final product had an IR in both the functional
region of the molecule and the fingerprinting region of the molecule. The match score
for this reaction was 92.73 % indicating that the graph was very highly accurate,
however there was a slight error. Towards the very edge of the produce IR there’s a very
small peak that was not supposed to be present. This is likely confirmation of something
of contaminant being presence in the final product but in very little amounts.

Standard Operating Procedures

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Standard Operating Procedures

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Daniel O Zamora 9-Fluorenone Reduction 07/13/2020

Procedure for this lab is on page 23 of the lab notebook.

1. Standard Operating Procedures

CAS No . PS Co lo r Odo r FP BP MP d VP VD Sol

Type s o f Ac ute Hazards /S ympto ms Pre ve ntio n Firs t Aid/Fire

CAS No . PS Co lo r Odo r FP BP MP d VP VD Sol

Type s o f Ac ute Hazards /S ympto ms Pre ve ntio n Firs t Aid/Fire

trans -p -Anis alac e to phe no ne

CAS PS Co lo r Odo r FP BP MP d VP VD Sol

Type s o f Ac ute Hazards /S ympto ms Pre ve ntio n Firs t Aid/Fire

p-Anis alde hyde

CAS No . PS Co lo r Odo r FP BP MP d VP VD Sol

Type s o f Ac ute Hazards /S ympto ms Pre ve ntio n Firs t Aid/Fire

Type s o f Ac ute Hazards /S ympto ms Pre ve ntio n Firs t Aid/Fire

5. Data and Results

Mass Product Obtained: 0.065 g

6. Data and Results Analysis

Figure 1: The drawn reaction for the reduction of 9-Flourenone.

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