Bromination of Arenes

Daniel O Zamora Bromination of Arenes 10/22/2020
Procedure for Bromination of Arenes on pg. 11
1. Standard Operating Procedures

a. Using Bromine
b. Waste Disposal
c. Wearing Gloves
d. Glassware
e. Using Organic Chemicals
2. Hazard Analysis
a. Bromine – Splashed into face accidentally
i. Danger: Can cause skin discoloration, inflamed eyes, and burn eyes.
ii. Avoid: Keep chemicals away from face. Wear goggles at all times
iii. What to do: Seek medical attention, thoroughly wash eyes/affected area
b. Dichloromethane – Inhaled deeply during reaction

i. Danger: Can cause multiple symptoms such as dizziness, numbness,
confusion, and nausea
ii. Avoid: Keep under a hood where there is ventilation
iii. What to do: Remove oneself from exposure and get medical attention
c. Toluene – Notebook placed on top of very hot hotplate next to full beaker
i. Danger: Paper igniting, knocking over beaker and spilling
ii. Avoid: Do not place notebook on hotplate or close to beaker
iii. What to do: Remove notebook. Turn off hot plate. Inquire over proper
cleaning procedure
d. Cyclohexane – Placed in test tube with big crack on the side

i. Danger: Spillage, can get on skin and cause irritation
ii. Avoid: Inspect glassware before use
iii. What to do: Contain spillage, clean up, wash affected area.
Bromine
CAS No. PS Color Odor FP BP MP d VP VD Sol

7726-95-6 liquid brown to irritating N/A 59 N/A 3.12 175 @ 7.14 4%
red 20
Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Hazard/Exposure
Fire Negligible fire hazard., may ignite or Avoid contact with Regular dry chemical,
explode on contact with combustible combustible materials carbon dioxide, regular
materials. foam
Inhalation Irritation, copious mucous secretion, Ventilation, local Remove from exposure
coughing, nosebleeds, and headache. exhaust. immediately; get
Delayed symptoms: nausea, diarrhea immediate medical
and abdominal pains, pulmonary attention.
edema, pneumonitis or pneumonia.
Skin Cooling sensation, burning sensation, Protective gloves and Remove contaminated
redness, pain, brown discoloration, clothing. clothes and jewelry,
blisters, discharging pustules, thoroughly wash skin with
destructive burns and deep-seated water, get medical
ulcers. attention immediately.
Eyes Redness, pain, blurred vision, burns, Safety goggles. Thoroughly wash eyes
lacrimation, photophobia, loss of with water for several
vision min, remove contact
lenses if possible, seek
medical attention
immediately, and continue
to wash eyes with water.
Ingestion Burns of the mouth, throat and Do not eat or drink in Contact physician
stomach, brown discoloration and the laboratory. immediately; give large
corrosion of the tongue and mucous amounts of water or milk
membranes, sore throat, and vomiting. and allow vomiting to
occur; when 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.
Cyclohexane

110-82-7 liquid colorless sweet -18 80.7 6.5 0.779 95 @ 2.90 insoluble
20

Hazard/Exposure
Fire SEVERE fire hazard., moderate No flames, no sparks, Regular dry chemical,
explosion hazard, vapors or gases may no contact with hot carbon dioxide, water for
ignite at distant ignition sources. sufaces. cooling, regular foam.
Inhalation Irritation, central nervous system Ventilation, local Remove from exposure
depression with headache, dizziness, exhaust. immediately; get medical
dullness, nausea, vomiting, attention.
degenerative changes in the heart,
lungs, liver, kidneys, and brain.
Skin Irritation, redness, and dryness. Protective gloves and Remove contaminated
clothing. clothes and jewelry,
thoroughly wash skin with
water.
Eyes Irritation, tearing, redness, and Safety goggles. Thoroughly wash eyes
conjunctivitis. 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
aspiration may result in chemical the laboratory. immediately. Give water
pneumonitis. or milk; if vomiting
than hips.
Carcinogenicity Not a known carcinogen. Mutagenicity Possible mutagen.
Cyclohexene

110-83-8 liquid colorless sweet -20 82 -104 0.8102 67 @ 2.8 insoluble
20

Hazard/Exposure
Fire SEVERE fire hazard., vapors or gases NO flames, NO Carbon dioxide, regular
may ignite at distant ignition sources. sparks, NO contact dry chemical, water.
with hot surfaces.
Inhalation Irritation, central nervous system Ventilation, local Remove from exposure
depression, headache, dizziness, exhaust. immediately, keep warm
drowsiness, labored breathing, and at rest. get medical
and kidney and liver damage. attention immediately.
Skin Defatting of the skin, redness, and Protective gloves and Remove contaminated
burning sensation. clothing. clothes and jewelry,
water.
Eyes Redness and irritation. Safety goggles. Thoroughly wash eyes

with water for several min,
Ingestion Nausea, labored breathing, central Do not eat or drink in If vomiting occurs, keep
nervous system involvement, the laboratory. head lower than hips;
pulmonary aspiration, and pneumonia. contact physician
immediately.
Dichloromethane

75-09-2 liquid colorless sweet none 40 -97 1.325 400 @ 2.9 1.32% @ 20
24

Hazard/Exposure
Fire Slight fire hazard. Avoid heat, flames, Carbon dioxide, regular
sparks dry chemical, and water.
Inhalation Irritation, lightheadedness, dizziness, Ventilation, local Remove from exposure
tingling, numbness of the extremities, exhaust. immediately; get medical
sensation of heat, sensation of fullness attention.
in the head, drunkenness, mental
confusion, nausea, headache, and
fatigue.
Skin Irritation, possibly burns, skin Protective gloves and Remove contaminated
absorption may occur causing effects clothing. clothes and jewelry,
detailed in inhalation. thoroughly wash skin with
water.
Eyes Pain, and extreme irritation. Safety goggles. Thoroughly wash eyes
with water for several
min, remove contact
lenses if possible, and
seek medical attention
immediately.
Ingestion Rapid, then slowed respiration, Do not eat or drink in If vomiting occurs, keep
gastrointestinal ulceration and the laboratory. head lower than hips; get
hemorrhage, and unconsciousness, medical attention, if
central nervous system depression, and needed.
liver and kidney damage.
Carcinogenicity Known carcinogen . Mutagenicity Possible mutagen.
Ethylbenzene

100-41-4 liquid colorless distinct 22 136 N/A 0.8670 7.1 @ 3.7 0.015%
20

Hazard/Exposure
Fire SEVERE fire hazard., vapors or gases Regular dry chemical,
No flames, no sparks,
may ignite at distant ignition sources. carbon dioxide, water
no contact with hot
for cooling, regular
surfaces.
foam.
Inhalation Severe irritation, cough, fatigue, Ventilation, local Remove from exposure
depression, dizziness, and headache. exhaust. immediately; get
medical attention
immediately.
Skin Irritation, inflammation, 1st or 2nd Protective gloves and
Remove contaminated
degree burns; absorption through skin clothing. clothes and jewelry,
may cause systemic toxicity. thoroughly wash skin with
water, get medical
Eyes Irritation and lacrimation. Safety goggles. Thoroughly wash eyes

min, remove contact
immediately.
Ingestion Abdominal pain, nausea, vomiting, Do not eat or drink in Contact physician
aspiration with extensive edema the laboratory. immediately. Give water
and hemorrhage of lung tissue. or milk; if vomiting
than hip.
Carcinogenicity Possible carcinogen. Mutagenicity Possible mutagen.
Methylcyclohexane

108-87-2 liquid colorless sweet -3 101 0.77 3.4 insoluble
-126– 37 @
-126.3 20

Hazard/Exposure
Fire Regular dry chemical,
Severe fire hazard., moderate No flames, no sparks,
carbon dioxide, water
explosion hazard, vapors or gases may no contact with hot
for cooling, regular
ignite at distant ignition sources. surfaces.
foam.
Inhalation Irritation, light-headedness, Ventilation, local Remove from exposure
drowsiness, lacrimation, salivation, exhaust. immediately, keep warm
labored breathing, diarrhea, and liver and at rest, get medical
and kidney damage. attention immediately.
Skin Irritation, hardening, ulceration, and Protective gloves and

Remove contaminated
defatting. clothing. clothes and jewelry,
water, get medical
attention.
Eyes Conjunctival congestion. Safety goggles. Thoroughly wash eyes

with water for several min,
Ingestion Irritation, lethargy, severe Do not eat or drink in Contact physician

diarrhea, liver and kidney damage, the laboratory. immediately. Give water
and circulatory collapse. or milk; if vomiting
than hips.

tert-Butylbenzene

98-06-6 liquid colorless mild 34 169 -58 0.867 4.79 3.16 insoluble
aromatic @ @
37.7 169

Hazard/Exposure
Fire Flammable. Emits toxic fumes under No flames, no sparks, Carbon dioxide, dry
fire conditions. no contact with hot chemical powder or
surfaces. appropriate foam. Water
may cool, but not
extinguish.
Inhalation May be harmful if inhaled. Ventilation, local Remove to fresh air. If
exhaust. breathing is difficult, give
oxygen.
Skin May be harmful if absorbed through Protective gloves and Immediately flush skin
skin. clothing. with soap and copious
amounts of water for at
least 15 minutes. Remove
contaminated clothing.
Eyes May be harmful to the eyes. Safety goggles. Immediately flush eyes
with copious amounts of
water lifting upper and
lower lids often. Seek
medical advice.
Ingestion 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.
Toluene
108-88-3 liquid colorless distinct 4 110.6 -93 0.865 22 @ 3.2 0.05% @ 20

20

Hazard/Exposure
Fire Severe fire hazard., vapors or gases may No flames, no Regular dry chemical,
ignite at distant ignition sources. sparks, no carbon dioxide, water for
contact with hot cooling, regular foam
surfaces.
Inhalation Fatigue, weakness, confusion, headache, Ventilation, local Remove from exposure
nausea, and drowsiness. exhaust. immediately; get medical
attention.
Skin Irritation and drying. Protective gloves Remove contaminated
and clothing. clothes and jewelry,
water.
Eyes Irritation and corneal burns. Safety goggles. Thoroughly wash eyes
min, remove contact
immediately.
Ingestion Abdominal spasms, systemic effects given Do not eat or Contact physician
in inhalation, coughing, and gagging. drink in the immediately. If vomiting
laboratory. occurs keep, head lower
than hips.
Carcinogenicity Not a known carcinogen. Mutagenicity Possible mutagen.
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 yield the time of reactions of five different
compounds. Carbon and Hydrogen bonds react according to how their chemical
environment. The compounds that are being tested vary on the type of carbon and
hydrogen bonds as either primary, secondary, and tertiary. Another variance between
the molecules that affect their rection times are the two groups are those that are
benzylic groups or aliphatic groups. Using these basic facts, a prediction will be made
and a determination of how accurate the predictions made were will be able to be
discussed.
5. Data and Results

Compound Reaction Time
Toluene 30 sec
Ethylbenzene 20 sec
tert-Butylbenzene No reaction
Cyclohexane 30 min
Methylcyclohexane 20 min
Table 1: These are the reaction times that were determined from a color change in solution.
6. Data and Results Analysis
The predicted order, in order from fastest to the slowest, is ethylbenzene, toluene,
methylcyclohexane, cyclohexane, and tert-butylbenzene. I predict this because we have
three major carbon-hydrogen bond groups in the tested molecules: benzylic groups,
aliphatic groups, and aromatic groups. Generally speaking, benzylic groups are more
reactive than aliphatic groups which are more reactive than aromatic groups. From
there it is also known that more substituted carbons are more reactive giving tertiary >
secondary > primary in terms of reactivity. Since toluene and ethylbenzene both have
carbon-hydrogen bonds that are connected to a benzene group both are likely to react
faster than the three remaining molecules, in addition ethylbenzene’s carbon-hydrogen
group that is bonded to the benzene is a secondary substituted carbon giving it more
hypothetical reactivity than the toluene whose group is a primary carbon. Finally, the
last three groups have aliphatic groups with methylcyclohexane having a tertiary
carbon-hydrogen group, cyclohexane has a secondary, and tert-butylbenzene has a
primary group. Taking the original prediction made with toluene and ethylbenzene, this
yields the originally stated prediction.
The reactions times were toluene - 30 seconds, ethylbenzene - 20 seconds, tert-
butylbenzene – no observable time, cyclohexane – 30 minutes, and methylcyclohexane
– 20 minutes. Although most of the reactions have a reasonable time and match the
prediction given tert-butylbenzene will be considered as an error. This is because
despite being the most unfavorable molecule for the reaction to take place it still had a
primary aliphatic group that could react and likely was reacting just not at rate that
allowed for it to be timed. This is why this last part is being considered an error since if
there was enough time to watch the reaction into its completion it is likely that time for
the reaction would’ve been obtained. However, due to the coronavirus pandemic, and
the fact that it is a teaching lab, the constraints on time were unavoidable. Other than
that, error the prediction was given time to analyze which is why the prediction
mirrored the reactions that were recorded. In addition, the procedure to be able to the
observe these reactions was not difficult and little effort was needed to avoid deviating
from the procedure, further limiting opportunity for error. The actual order tells us that
bond strength, stabilization, and energy available affects and essentially limits the speed
of the reactions.
7. Discussion
This experiment functioned on the principle of homolytic cleavage of Br 2. The
mechanism from this reaction comes from each Bromine being turned into a bromine
radical the radicalized Bromine atom can then interact with a hydrogen atom in a
Hydrogen-Carbon bond. That bond then undergoes its own homolytic cleavage which
allows the radicalized bromine atom to bind to the hydrogen leaving a radicalized
carbon atom, with whatever it is attached to, to be able react with another radical. This
radicalized carbon atom can then interact with another Br2 molecule and cause a
homolytic cleavage and form a bond with the bromine it interacted with leaving a
radicalized bromine behind. The energy for this reaction comes from light, energy that
light provides is enough to induce homolytic cleavage which can set this reaction in
motion. Something to note is that in this mechanism it is assumed that the radicalized
carbon goes and interacts with another Br2 molecule and not the left-over radicalized
bromine atom that was previously left over. This is because as the reaction starts it is
highly more likely for the radicalized carbon atom to bump into a Br 2 molecule than the
few radicalized atoms of bromine that are in solution at the beginning. In other words,
there is an excess of Br2 that was added in the beginning. The concepts of these
experiments, and of the speed of the reactions, come from the stability and electron
density. Primary hydrogens have bonds that require more energy to break than
secondary hydrogens which require more energy than tertiary hydrogens. Yet, the
radicalized carbon atoms are stabilized by nearby electron density, which creates the
conditions that allows the radical to be formed in certain areas and how molecules that
have benzoic groups create the condition in which radicalization on carbon atoms
bonded to them are favored. These factors create the unique conditions in which cause
the difference in times in reactions in these molecules. For ethylbenzene having a
secondary benzoic group create the conditions in which reaction with this area would be
much more preferred than the aromatic and aliphatic groups and placing it at a higher
speed reaction than the rest of the molecules. For toluene the situation differed slightly.
This group had an aliphatic site it also had a primary benzoic site, because of this its
reaction time was second in terms of speed. The last three all had in common aliphatic
groups. It is worth to mention that tert-butylbenzene has an aromatic group but
because it is less reactive than the aliphatic group, due to the fact that halogens are not
electrophilic enough to react with the benzene group, this gives aliphatic groups
priority. This means that since they all have aliphatic groups, all of their rection speed
have to be compared on whether the groups are primary, secondary, or tertiary to
determine reactivity. The tertiary aliphatic, in methylcyclohexane, will then create the
conditions that will both create the hydrogen and carbon bond that can easily be broken
with low amounts of energy and can simultaneously stable the radicalized carbon,
making it the third in reaction time. Finally, it since the last two remaining groups have a
secondary aliphatic, cyclohexane, and a primary aliphatic for tert-butylbenzene they
subsequently fall into the fourth and fifth place. These previous explanations give insight
into chemistry that largely revolves on energy, stabilization, and interactions that
determine the speed of reaction of all five molecules. It also explains the relatively
simple procedure that essentially only need Br2, the tested groups, and lights to run.
Dichloromethane functioned as the organic solvent in this experiment. Lastly, when it
comes to tert-butylbenzene, a specific time of reaction was not given and was
considered a no reaction. This is most likely false since the molecule did have sites
where radical bromination was possible, but it is likely that the reaction was slow
enough that the time that was given to perform this experiment was not enough. This
ranges from multiple explanations from not enough energy from light to break the
primary aliphatic group bond that held the hydrogen bonded to the carbon to poor
stabilization on the carbon radical. With enough time it is likely that this reaction
would’ve gone to completion. Lastly, one the reactions are completed, indicated by the
color change, cyclohexene is added to neutralize the Br2 that remains. The electron rich
environment from the double bond in cyclohexene allows for a perfect reaction that can
allow it to become 2-bromocyclohexane.
8. Conclusion
The results of this experiment gave the order of reaction for the different molecules to
be toluene - 30 seconds, ethylbenzene - 20 seconds, tert-butylbenzene – no observable
time, cyclohexane – 30 minutes, and methylcyclohexane – 20 minutes. This largely
matched the prediction that used knowledge about how organic chemistry functions to
be able to approximate an order, from fastest to slowest, that matched the results in
the lab. The predicted order was ethylbenzene, toluene, methylcyclohexane,
cyclohexane, and tert-butylbenzene. Finally, due to the simplicity of the experiment
almost no errors were reported but due to lack of time the tert-butylbenzene reaction
was not able to run to its completion. The chemistry of tert-butylbenzene shows that it
has available groups for this reaction to take place but due to factors like stronger
hydrogen-carbon bonds and less stabilization of the carbon radical. So, while it was
treated as a no reaction it is likely that there was reaction occurring just at a slow
enough rate that the went over the amount of time that the lab allotted for this
reaction.

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Daniel O Zamora Bromination of Arenes 10/22/2020

Procedure for Bromination of Arenes on pg. 11

1. Standard Operating Procedures

b. Dichloromethane – Inhaled deeply during reaction

d. Cyclohexane – Placed in test tube with big crack on the side

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

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

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

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

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Carcinogenicity Not a known carcinogen. Mutagenicity Possible mutagen.

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

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Eyes Redness and irritation. Safety goggles. Thoroughly wash eyes

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

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

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Carcinogenicity Known carcinogen . Mutagenicity Possible mutagen.

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

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Eyes Irritation and lacrimation. Safety goggles. Thoroughly wash eyes

Carcinogenicity Possible carcinogen. Mutagenicity Possible mutagen.

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

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Skin Irritation, hardening, ulceration, and Protective gloves and

Eyes Conjunctival congestion. Safety goggles. Thoroughly wash eyes

Ingestion Irritation, lethargy, severe Do not eat or drink in Contact physician

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

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

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

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

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

108-88-3 liquid colorless distinct 4 110.6 -93 0.865 22 @ 3.2 0.05% @ 20

Types of Acute Hazards/Symptoms Prevention First Aid/Fire

Carcinogenicity Not a known carcinogen. Mutagenicity Possible mutagen.

5. Data and Results

6. Data and Results Analysis

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