Paracetamol Synthesis

Paracetamol Synthesis
Subjectively, and in conjunction with reparative reasons, for this paper, I am choosing a very
common over the counter for natural ailments such as sore head and inflammatory pain reliever and
cold medicine. In contrast, it is usually found at many Walmart's, and brands and brands of
Pharmacies. Altogether, this drug gathers strength of sales from America's woes with migraines and
headaches for a medication blockbuster on the market. From across the nation, to around the world,
it is one of the biggest pharmaceutical giants dominating the marketplace. There are numerous
names some common such as acetaminophen, or in other world markets as known as paracetamol.
The branded name by Johnson & Johnson is Tylenol and is a shortening of the chemists ... Show
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(Wikipedia, 2016) under Paracetamol as having the following chemistry structure: "Paracetamol
consists of a benzene ring core, substituted by one hydroxyl group and the nitrogen atom of an
amide group in the para (1, 4) pattern. The amide group is acetamide (ethanamide). It is an
extensively conjugated system, as the lone pair on the hydroxyl oxygen, the benzene pi cloud, the
nitrogen lone pair, the p orbital on the carbonyl carbon, and the lone pair on the carbonyl oxygen are
all conjugated. The presence of two activating groups also makes the benzene ring highly reactive
toward electrophilic aromatic substitution. As the substituents are ortho, para directing and para with
respect to each other, all positions on the ring are more or less equally activated. An atom of an
amide group in the para (1, 4) pattern. The amide group is acetamide (ethanamide). It is an
extensively conjugated system, as the lone pair on the hydroxyl oxygen, the benzene pi cloud, the
nitrogen lone pair, the p orbital on the carbonyl carbon, and the lone pair on the carbonyl oxygen are
all conjugated. The presence of two activating groups also makes the benzene ring highly reactive
toward electrophilic aromatic substitution. As the substituents are ortho, para directing and para with
respect to each other, all positions on the ring are more or less equally
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Nitration Of Methyl Benzoate Lab Report
The purpose of this experiment is to study an electrophilic aromatic substitution. With observing this
substitution, the identity of the major product will be discovered. The method used to reach the
purpose of the experiment is a TLC. The nitration of methyl benzoate with a mixture of sulfuric acid
and nitric acid will be performed in the experiment. NO2 is the electrophile in the experiment, and it
is an electron withdrawing group that makes the methyl benzoate less reactive. The NO2 group in
this nitration can be added to three different positions –ortho, para, or meta. When the NO2 is added,
it makes a methyl nitrobenzoate. The weight recorded of methyl benzoate in the start of the
experiment is 3.397 grams. The weight of the crude product

Preparing A Yield Of Tert Butylchloride Through A...
Objective The objective of the experiment was to prepare a yield of tert–butylchloride through a
unimolecular (SN1) nucleophilic substitution reaction. Procedure Part A– Preparation of tert–Butyl
Chloride A test tube was acquired, and 7 mL of concentrated HCl were added to this test tube
through a graduated cylinder, this was done in the fume hood in order to avoid any noxious fumes
from the sample, which were observed when pouring in the concentrated HCl. After adding the HCl,
a glass pipet was used to add 2.5 mL of tert–butyl alcohol to the test tube. It was observed that the
alcohol and HCl separated into two layers distinct layers. The solution was mixed by using the pipet
to take the bottom layer and squirt it onto the top, this mixing process was performed for 15 minutes
to allow the solutions to mix well. Afterwards, the lower aqueous layer of the test tube was removed
with the pipet; it was imperative to remove as much of the lower layer as possible without removing
too much from the top layer. The solution was then washed with water by pouring 2.5 mL of water
into the test tube, letting it sit for about a minute and then removing the aqueous layer again, in
order to help the mechanism for this process. Additionally, about 2.5 mL of sodium bicarbonate 5%
were also added to he test tube, were allowed to sit for about a minute, and then removed once
again; this was done in order to remove any HCl impurities from the solution. The remaining upper
layer was moved to

Aromatic Substitution : Nitration Of Bromobenzene And...
CH 220C – Organic Chemistry Lab
Experiment 13: Electrophilic Aromatic Substitution: Nitration of Bromobenzene and Relative Rates
of Reaction
Rodan Devega
Introduction Electrophilic aromatic substitution (EAS) reactions involve the replacement of a
hydrogen atom bonded to an aromatic compound by an electrophile. The rate and direction of the
EAS reaction depends on the functional groups present on the aromatic compound. The purpose of
this experiment was to synthesize bromonitrobenzene by reacting bromobenzene with sulfuric acid
and nitric acid via EAS. Gas chromatography (GC) was performed on the product in order to
confirm its identity by comparing its observed retention time to the true retention time of
bromonitrobenzene. Additionally, the relative rates of reaction for several substituted aromatic
compounds were predicted and examined via reaction with molecular bromine. The rates were than
compared to gain insight on the affect of different substituents on rates of reactions concerning
aromatic compounds.
Data and Results
Table 1. Relative rates of various EAS reactions.
Compound
Elapsed Time (s)
Temperature (C)
Phenol
1.0
35
4–Bromophenol
4.0
35
Anisole
7.0
35
Acetanilide
> 60.0
35
Diphenyl Ether
>> 60.0

35
The order of EAS rates, from fastest to slowest, is as follows: phenol, 4–bromophenol, anisole,
acetanilide, and diphenyl ether.
Table 2. GC product analysis of bromonitrobenzene.
Peak Number
Time (min)
Area (uV*sec)
Height (uV)
Area (%)
1
0.482
599
862
0.14
2

Nitration of Methyl Benzoate Essay
Nitration of Methyl Benzoate
Abstract: This procedure demonstrates the nitration of methyl benzoate to prepare methyl m–
nitrobenzoate. Methyl benzoate was treated with concentrated Nitric and Sulfuric acid to yield
methyl m–nitrobenzoate. The product was then isolated and recrystallized using methanol. This
reaction is an example of an electrophilic aromatic substitution reaction, in which the nitro group
replaces a proton of the aromatic ring. Following recrystallization, melting point and infrared were
used to identify and characterize the product of the reaction.
Purpose: The purpose of this experiment is to synthesize methyl nitrobenzoate from methyl
benzoate, concentrated nitric acid, and concentrated sulfuric acid via an ... Show more content on
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The product attained was a white, dry solid. The small amount of product lost during the second
recrystallization was most likely do to impurities, which were filtered away with the methanol.
Impurities that contributed to the low percent yield could be due to side reactions such as methyl o–
nitrobenzoate and methyl p–nitrobenzoate. Although the percent yield attained was low, the product
attained was fairly pure due to similarity in melting point and IR spectrum compared to standardly
accepted values for methyl m–nitrobenzoate.
Spectrum:
C–H stretch of the aromatic ring near 3100 cm–1
Strong peak near 1750 cm–1 representing the carbonyl ester stretch Two NO2 stretches at 1530 cm–
1 and a little under 1300 cm–1
Aromatic C=C stretch near 1600 cm–1.
The IR spectrum attained also contained a slightly broad stretch between 3200–3600 cm–1, this
could be indicative of a phenol group present or an alcohol impurity. One theory to this impurity
may be due to a dirty salt plate used during the spectra reading. Alcohol residue could be remaining
on the plate from previous laboratory experiments.
Questions: 1. Why is methyl m–nitrobenzoate formed in this reaction instead of ortho or para
isomers?
Methyl m–Nitrobenzoate is formed in this reaction rather than ortho/para isomers because of the
ester group of your starting product of methyl benzoate. The ester group on the ring is an electron–
withdrawing group

Electrophilic Aromatic Substitution Reaction Lab Report
The purpose of this experiment was to nitrate methyl benzoate through electrophilic aromatic
substitution reaction.
Introduction
Electrophilic aromatic substitution reactions take place with an aromatic compound, compound with
high electron density, and an electrophile a compound which is partially positive. One of the pi
bonds in the benzene donates electron to the electrophile which leads to an electron deficient
adjacent carbon, carbocation. This carbocation is also known as an arenium ion. This arenium ion
formation leads to non–aromaticity which is not as stable as the aromatic compound. The reaction
undergoes elimination where a base deprotonates from an adjacent carbon leading to a formation of
a pi bond and restoring aromaticity. ... Show more content on Helpwriting.net ...
The electron withdrawing property of the deactivators is due to resonance and inductive effects.
When the substituent is a deactivator it directs the electrophile in the meta position. This is seen in
resonance structures as in the meta position the positive charge in not on the carbon that has the
deactivator substituent attached to it. This prevent instability and the energy required for this
reaction is lower in comparison to ortho and para positions Meanwhile, the resonance structures of
ortho and para put the positive charge on the carbon bearing the electronegative atom, deactivator,
which leads to

Synthesis of 3-Nitrobenzaldehyde Essay
Abstract
This experiment is about the synthesis of 3–nitrobenzaldehyde through nitration. The nitration of
benzaldehyde is an example of an electrophilic aromatic substitution reaction, in which a proton of
an aromatic ring is replaced by a nitro group. Many aromatic substitution reactions are known to
occur when an aromatic substrate is allowed to react with a suitable electrophilic reagent, and many
other groups besides nitro may be introduced into the ring. Although the reaction produced a low
yield at the end, the yield is calculated from the reaction and limiting reagent.
Keywords: electrophilic aromatic substitution, nitration, aldehyde, nitrating group
Introduction
Electrophilic substitution happens in many of the ... Show more content on Helpwriting.net ...
Stage 1 of the mechanism of nitration
As the NO2+ ion approached the delocalised electrons in the benzene, those electrons were strongly
attracted toward the positive charge.
Two electrons from the delocalised system were used to form a new bond with the NO2+ ion.
Because those two electrons aren't a part of the delocalised system any longer, the delocalisation
was partly broken, and in the process the ring gained a positive charge.
Stage two
Figure 2. Stage 2 of the nitration mechanism
The second stage involved a hydrogensulphate ion, HSO4–, which was produced at the same time as
the NO2+ ion. This removed a hydrogen from the ring to form sulphuric acid – the catalyst had
therefore been regenerated. The electrons which originally joined the hydrogen to the ring were now
used to re–establish the delocalised system.
Table 1. Observations from the experiment proper
Observations:
89 mL conc. H2SO4
Clear solution
+ 45 mL fuming HNO3
Clear solution
+ 10.2 mL benzaldehyde
Solution turns yellow if stirred continuously while adding benzaldehyde. But solution will produce
red orange fumes and increase heat.

+ ice
White fluffy precipitate
After vacuum filtration
White gum–like precipitate
+ 125 mL diethyl ether
Precipitate dissolves and solution turns into pale yellow color
+ 125 mL 5% NaHCO3
Immiscible with solution. Golden yellow in color.
While the experiment was being executed,

Substitution Reactions ( Sn2 And Sn )
Using various alcohols, the substitution reactions (Sn2 and Sn) were utilized by helping with which
functional groups reacted, in which way. Developing a mechanism for the alcohols are discussed.
This journal inspects the substitution reactions occurring in the alcohol–containing compounds.
When a substitution reaction transpires, it substitutes one sigma (σ) bond with another sigma (σ)
bond. In substitution reactions, there are two types that are focused when working with organic
molecules, Sn1 and Sn2.
A Sn1 reaction is a nucleophilic substitution reaction, which has one molecule that is in the rate–
determining step of the reaction. This simply means there is one substitution that occurs before the
final product is created. A Sn2 reaction is, also, a nucleophilic substitution reaction. The Sn2
reaction has two molecules that are in the rate–determining step; therefore, two substitutions occur
before the final product is created (reactions occur simultaneously).
The three different types of alcohols that were utilized during this experiment are common in Sn1
and Sn2 reactions. The reaction that occurs between the alcohol and the solvents are both Sn1 and
Sn2 reactions.
While working with reaction 1 there are several different chemical properties to be aware of, 3–
Phenyl–1–propanol has a melting point of –18°C. It also has a boiling point of 119°C. The density
of the alcohol us 1.001 g/mL. In reaction 2, the boiling point of 2–pentanol is 119°C. The melting
point of

Advantages And Disadvantages Of Diazonuim Salts
Introduction:
Diazonuim salts are unsaturated compounds which have a trible bond.
There was a scientist his name was Griess, this scientist gave Diazo name to diazonuim salts as he
thought that two hydrogen atoms in the benzene ring will be replaced by two atoms of nitrogen.
Diazonuim salts divided into two types of salts:
Aromatic diazonuim salts and alephatic ( non– aromatic) diazonuim salts.
Non aromatic salts are less important than aromatic.
Under normal conditions, diazonuim salt is highly unstable.
Dizonuim salts have some properites such as shock–sensitive, decompose violenthly when heating
and they can conduct electricity, for this reason they are considered one of the electrolyte
compounds.
There are a lot of types of diazonuim ... Show more content on Helpwriting.net ...
There is a type of reaction in which Nitrogen atom doesn't realese from the salt. This type of
reaction is called reduction reaction, it done by using SNCl2 or Na2So3 to give hydrasin derivatives.
There is another type of diazonuim salts reactions which lead to the formation of azo dyes
compounds, this reaction is done by adding some compounds to the salt such as, aromatic amines,
compounds which have keton group in its structure like aceton, compounds which have OH group
like phenol or naphthalen and hetrocyclic compounds in two steps:
– Step 1:
Formation of diazonuim salt.
– Step 2:
React diazonuim salt with coupling component which may be phenol or any type of aromatic
amines so, a stable azo dye will be formed.
Azo dyes compounds have different structures as most of them contain only one azo group, but they
may contain two or three or more azo groups.
Another methods of reactions
. SN1 reaction.
. sandmeyer reaction.
. gattermann reaction.
. baltz–schiemann reaction.
1– SN1 reaction:
On heating, diazonuim salts decompose into nitrogen and aryl cation which is could be attacked by
any nucleophile due to its

Iodination Of Salicylamide Lab Report
Iodination of Salicylamide Purpose The purpose of this experiment is to study the directing effects
of substituents on an aromatic ring. Aromatic rings do not undergo electrophilic addition reactions
instead they undergo electrophilic aromatic substitution. The study will be made from the reaction of
the electrophile, iodide ion with sodium hypochlorite, with salicylamide that has a hydroxyl group
(ortho–/para– directing) that is highly activated, electron donating, and an amide group (meta–
directing) that is deactivating, electron withdrawing. The effects of the resulting substitution patterns
will be done by analyzing infrared (IR) spectroscopy of the product to determine where on the ring
the iodine substitution occurs. Reactions Reaction 1: the ... Show more content on Helpwriting.net ...
The hydroxyl group set the directing effect for the product to have the iodine be placed para– to the
hydroxyl group. IR spectrum showing a strong peak at 816.50 cmˉ¹ in the fingerprint region
suggested a ring substitution pattern of 1, 2, 4– Trisubstituted because this pattern is expected to
have peaks between 850– 800 cmˉ¹. The melting point being 210.8°C –216.4 °C suggested the
structure to be like the melting point of 228°C of 5–iodosalicylamide. The identification was
determined to be 5–iodosalicylamide because of the directing effects of the activating group and the
results of the melting and IR spectrum of the product formed. Error resulted in the melting point
being lower than the actual melting point of the suggested salicylamide product structure because
the sample could have been not as pure. Further error could have resulted in the procedure of the
experiment of timing or in the addition of compounds to the solution. Further experimentation
would need to be done to further confirm the results of the suggested identity of the

Bromopropane And Potassium Hydroxide Lab Report
The purposes of this experiment were to model a bimolecular nucleophilic substitution reaction
between potassium hydroxide (KOH) with 1–bromopropane and determine whether it follows a
second–order rate law mechanism. A rate constant of 0.0684 M–1 min–1 was obtained for this
reaction at 45.1°C, which was determined through equilibrating the reaction and performing
titrations of 0.390 M KOH with 0.1000 M hydrochloric acid (HCl). The activation energy calculated
from class data was 50.188 kJ/mol, which deviated largely from the literature range value of 72.80–
83.76 kJ/mol. It was concluded that the reaction was consistent with the predicted SN2 mechanism,
based on the regression of a trendline.
Many reactions that exist in nature involve a double displacement between ions and reactants with
solvents. A bimolecular nucleophilic substitution, or SN2 reaction, involves a nucleophilic attack on
a substrate and the departure of a leaving group. A nucleophile is a compound or ion that donates
electrons to promote bond formation (Caldwell, 1984). In order for a leaving group in a compound
to leave, it must possess the characteristics of a weak base and be able to occupy electrons. Several
factors affect the rate and favorability of such reaction, such as (Bateman, 1940). In addition, the
substrate that is attacked by the nucleophile is commonly an unhindered primary substrate to allow
the reaction to occur quicker. An SN2 reaction follows the second–order rate law. In this

Friedel-Crafts Acylation Lab Report
The Friedel–Crafts acylation reaction is an important and valuable electrophilic aromatic
substitution reaction. First introduced in 1912 by Charles Friedel and James M. Crafts, this reaction
allows large multi–step reactions to take place, and creates numerous types of products.1 Today,
Friedel–Crafts reactions are among the most used electrophilic aromatic substitution reactions. In
the electrophilic aromatic substitution class of reactions, functional groups are substituted onto an
aromatic ring.2 Products such as ketones, hydrocarbons and phenols, phenol ethers, and keto acids
can be produced by electrophilic aromatic substitution.1 These products can then undergo other
reactions, allowing for the creation of many types of products. The products acquired can be used
for a range of purposes, such as pharmaceuticals, pesticides, dyes, etcetera.3 In particular, Friedel–
Crafts acylation reactions result in a product containing a ketone. ... Show more content on
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The functional group added during a Friedel–Crafts acylation reaction, deactivates the ring, resulting
in a mono–substituted ring rather that a poly–substituted ring, which is produced from a Friedel–
Crafts alkylation reaction.4 The mono–substituted product is then further reduced to get an alkyl
substituted ring instead of yielding a product containing a ketone. To obtain the ketone product, an
acyl group is added to an aromatic ring. However, for this reaction to take place, no electron
withdrawing groups can be present on the aromatic ring, and an acyl halide must be used to obtain
the acyl cation.5 These limitations are met, in the Friedel–Crafts acylation reaction of anisole with
acetyl

The Aromatic Substitution : Preparing Methyl M Nitrobenzene
Electrophilic Aromatic Substitution: Preparing Methyl m–nitrobenzene
Shultz, Joshua T.
Chemistry 2210L
Data
Table 1. Mass and volumes of reagents and recovered product with experimental melting point.
Reagents Mass/Volume
Methyl Benzoate 1.50 mL
Concentrated H2SO4 4.0 mL
Concentrated HNO3 2.0 mL
Products Mass
Methyl m–nitrobenzoate 2.5607 g
Experimental Melting Point 64–70 °C
Results and Calculations
Equation 1. Balanced reaction for nitration of methyl benzoate.
Calculation 1. Theoretical yield of methyl–m–nitrobenzoate from 4.0 mL of concentrated HNO3
(excess).
4.0 "mL HNO3 "×(1.42 "g HNO3 " )/"mL HNO3 " ×(1 "mol HNO3 " )/(63.01 "g HNO3 " )×(1 "mol
methyl m–nitrobenzoate" )/(1 "mol HNO3 " )
×(181.14 "g methyl m–nitrobenzoate" )/(1 "mol methyl m–nitrobenzoate" )
=16.32876051 "g methyl m–nitrobenzoate"≈16 "g methyl m–nitrobenzoate"
Calculation 2. Theoretical yield of methyl–m–nitrobenzoate from 1.50 mL of methyl–benzoate
(limiting reagent).
1.50 "mL methyl–benzoate "×(1.094 "g methyl–benzoate " )/"mL methyl–benzoate " ×(1 "mol
methyl–benzoate " )/(136.15 "g methyl–benzoate " )

×(1 "mol methyl m–nitrobenzoate" )/(1 "mol methyl–benzoate " )×(181.14 "g methyl m–
nitrobenzoate" )/(1 "mol methyl m–nitrobenzoate" )
=2.183259199 "g methyl m–nitrobenzoate"≈2.18 "g methyl m–nitrobenzoate"
Calculation 3. Percent yield of "Methyl m–nitrobenzoate" .
"Experimental Yield" /"Theoretical Yield" ×100=(2.5607" g methyl m–nitrobenzoate"
)/(2.183259199 "g methyl

Synthesis Of T-Butylbenzene Lab Report
he electrophilic aromatic substitution reaction leads to form 1,4–di–t–butylbenzene from the
reaction of benzene and t–butyl chloride. The t–butyl cholride is considered not electrophilic enough
to react with benzene, so it needs aluminium chloride catalyst to make it strong electrophile.
Aluminium chloride is a lewis acid. The chloride atom will be separated from t–butyl chloride and
attached to the aluminium chloride to become AlCl4. So, the t–butyl will be a carbocation, and it
will be good electrophile due to its ability to form carbon–carbon bond.
( The equation of AlCl3).
( The mechanism of AlCl3).
The electrophile, t–butyl cation, reacts with benzene. One of the three pi bonds of the aromatic ring
will form a sigma bond with the t–butyl cation. The t–butyl cation will attach to the aromatic ring.
This leads ... Show more content on Helpwriting.net ...
This is because the alkyl group substituent has lone pairs of electron, so it is electron donating
group. This leads to activate the aromatic ring through its work on increasing the electron density on
the aromatic ring by the effect of resonance. The resonance with para position will give carbocation
on two secondary carbons and one tertiary carbon. Para position makes the compound strongly
stable because the alkyl group will push the electrons toward the carbocation on tertiary carbon on
the ring.
Mechanism 000000000000000
The resonance with ortho position, like para position, gives one carbocation on tertiary carbons,
which is the carbon that is next to the substituent. Also, ortho position gives carbocation on two
secondary carbon. The positive charge on the tertiary carbon on the ring makes it more stable
because of its location next to electron donating group which pushes the electrons toward the ring.
Both ortho and para positions forms a carbocation of the tertiary carbon. But, para position is more
common. This is because of the effect of steric

The Effect Of Metoprolol On The World Health Organization...
METOPROLOL
Introduction
Metoprolol is a selective β1 receptor blocker.1 It is used to treat high blood pressure or
hypertension, myocardial infarction (MI), heart failure and angina pectoris.2 Metoprolol was first
made in 1969 and is on the World Health Organization's list of essential medicines.3 Metoprolol is
available only in its salt form due to its low melting point, such as metoprolol tartrate or metoprolol
succinate. Its salt form, metoprolol tartrate was first developed by Novartis and was approved by
FDA on August 7, 1978.4 Metoprolol is also available as a generic drug.1
Drug Profile Figure 1. Chemical Structure of Metoprolol
IUPAC Name : 1–(isopropylamino)–3–[4–(2–methoxyethyl)phenoxy] propan–2–ol
Chemical Formula : C15H25NO3
Molecular Weight : 267.364 g/mol
Trade names : Lopressor, Metolar XR, Toprol XL (US)
Nature : Free base exists as a white solid, while its tartrate form exists a fine crystalline material.5
Physical properties* : Solubility – Very soluble (water), Freely soluble (methylene chloride,
chloroform, alcohol), Slightly soluble (acetone) and Insoluble (ether).6 Melting point – 120°C or
248°F.5
*Properties are given, considering the salt form, metoprolol tartrate.
Pregnancy category : C (US). Indicates that it's a risk when used during pregnancy.
Route of administration : Oral and Intravenous (IV)
Pharmacokinetic data : Bioavailability – 50%7 Protein binding – 12% Metabolism – Liver via
CYP2D6, CYP3A4 Half–Life – 3–7 hours

Introduction
An organic reaction of aromatic compounds in which a positive ion or other electron–deficient
species with a full or large partial positive charge known as an electrophile replaces a hydrogen
bonded to a carbon of an aromatic ring is known as an electrophilic aromatic substitution reaction.
This reaction is very important for aromatic compounds allowing the direct introduction of groups
placements and providing synthetic routes to many important compounds.1
Aromatic rings like benzene are susceptible to electrophilic attacks but rather than addition reactions
they undergo substitution reactions. Substitution reactions allow the pi electrons in benzene to
regenerate after being attacked by the electrophile.1 In step one of an electrophilic aromatic
substitution reaction, an attack of the electrophile by a pi bond of the aromatic ring occurs. The
electrophile takes two electrons of the aromatic system to form a sigma bond to one carbon atom of
the benzene ring. This bond formation interrupts the cyclic system creating a resonance–stabilized
carbocation called an arenium ion. In the next step removal of a proton breaks the C–H bond and a
C–C pi bond occurs ... Show more content on Helpwriting.net ...
All six reactions involve the use of an addition of a Lewis acid. In the case of chlorination and
bromination, a Lewis acid such as AlCl3 or FeBr3 accepts a pair of electrons from the Br2 or Cl2.
This weakens the bond between the halogen making it a better nucleophile and creates a better
leaving group. Nitration is the substitution of hydrogen with nitrogen dioxide. It uses nitric acid as
the source of nitrogen dioxide and sulfuric acid as the Lewis acid. Just like nitration, sulfonation
uses sulfuric acid as its Lewis acid. Sulfonation replaces a hydrogen with a sulfuric acid group and
can be performed using sulfur

Electrophilic Aromatic Cation Lab Report
The purpose of this experiment was to perform a nitration of a monosubstituted arene by
electrophilic aromatic substitution and the second part of the experiment was to determine the
relative reactivities of five different arenes using electrophilic aromatic bromination.
DISCUSSION AND CONCLUSION
In electrophilic aromatic substitution, an atom that is attached to an aromatic compound is replaced
by an electrophile. The stability of aromatic rings makes the need for a very strong electrophile for
the molecule to be formed. Nitro–groups and halogens are good examples of the kind of
electrophiles that should be used. The rate of the reaction and direction are affected by the
electrophile. A carbocation intermediate is formed when the electrophile attacks one of the double
bonds on the molecule and breaks it. The double bond can be reformed by a nucleophile that attacks
it as a base. As stated, a very strong electrophilic ion is needed to change the stability of the
aromatic ring. In the case of two electrophiles, the stronger one should be used to create the strong
cation which can then break the double bond.
An aromatic compound with a functional group on it creates three different isomeric products
because substitution can happen in either the otho–, meta–, ... Show more content on
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The ring activating reactants were electron donating because they had electron lone pairs and
therefore reacted faster. The reactants that were ring deactivating reacted slower because of they
were attached to electron withdrawing groups. The reaction order from fastest to slowest was as
predicted with phenol being the fastest, then anisole, 4–bromophenol, acetanilide, and diphenyl
ether being the slowest due to the electron withdrawing group joined to it. These outcomes are
constant with the concepts of ring activating and deactivating functional

Electrochemistry: Diazonium Scarce Reactions
In this experiment, stereochemistry was observed. Azo violet is a compound that contains an azo
group. This group is comprised of a N=N double bond. Therefore, due to its extensive conjugation
within the molecule, it is highly colored and used in the textile industry as a dye frequently. For this
experiment, the azo violet will be synthesized and a diazonium coupling reaction will occur. A
diazonium coupling is an electrophilic aromatic substitution where the electrophile is the terminal
nitrogen atom of the diazonium salt. The diazonium salt from p–nitroaniline will first be
synthesized. This is achieved by reacting the p–nitroaniline with HCl and nitric acid. Secondly, the
azo violet will be prepared from the electrophilic aromatic substitution ... Show more content on
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These dyes are made from a N=N double bonded to another nitrogen with two aromatic rings. Many
different functional groups however could be added to different positions on the rings to create a
large variety of different dyes. The conjugation present between these aromatic rings is caused by
the N=N double bond. With the presence of extended conjugation, it causes the colors of the visible
spectrum. The formation of azo dyes occurs in two steps. The first step is the process of the
diazotization which is converted into an aromatic amine, p–nitroaniline, which combines with
sodium nitrite and HCl to form an azide salt. In the second step, diazonium coupling occurs which is
an electrophilic aromatic substitution. In the presence of the second aromatic ring along with the
azide salt, resorcinol forms. Resorcinol attacks the azide to product the only product possible, azo
violet. Only one azo violet dye is produced due to the configuration of the hydroxy groups present
on the ortho para directors, so the alcohol groups both point to the exact same carbon. Substitution
cannot occur since excessive steric hindrance is present. Since only one product can be formed,
there is no reason to perform recrystallization and only the nonreacted reactants must be

Methyl Orange Synthesis Lab Report
Experiment 11B consisted of synthesizing methyl orange, a synthetic dye, and testing this dye's
coloring quality and effectiveness as a pH indicator. Methyl orange is an acid–base indicator. In a
pH of greater than 4.4, it becomes a yellow solution with a negatively charged sulfonate ion. When
submerged into a solution with a pH less than 3.2, the dipolar red ion (helianthin) predominates.
Methyl orange is a type of azo dye, which is commonly found in food, fabric, paint, and other
brightly colored products. The general structure consists of the N5N functional group sandwiched
between two aromatic species. Azo dyes are brightly colored because of their extensive conjugated
system which gives rise to a strong chromophore. The exact color depends on both the nature of the
aromatic group and the substituents. Methyl orange is synthesized through an azo coupling reaction
between a diazonium ion and N,N–dimethylaniline. An electrophilic aromatic substitution causes
the positively charged diazonium ion to act as the electrophilic species. In the first step of azo
coupling the diazonium intermediate is synthesized. This process is called diazonation, in which the
diazonium intermediate is formed by the reaction between sulfanilic acid (an aromatic amine) ...
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After this we added .5g of NaCl and allowed the solution to cool to room temperature then placed it
into an ice bath. The reaction mixture turned into a lighter shade of yellow and began to crystallize.
The crystals were filtered through a Buchner funnel and rinsed twice with saturated aqueous NaCl
solution. The reaction mixture was placed in a boiling water bath in order to dissolve most of the
dye and all the contaminating salts. It was then cooled in a ice bath and filtered using a Buchner
funnel. The product obtained was shiny and a metallic gray–gold color. The product weighed in at
.207g of methyl orange, giving us a percent yield of

Electrophilic Aromatic Substitution And Column...
Experiment FIVE: Electrophilic Aromatic Substitution and Column Chromatography Reaction
Procedure A hot plate was preheated to 100°C. A dry 5–mL long–neck round–bottom flask was
clamped over an aluminum block placed on the hot plate. Ferrocene (0.09 g), acetic anhydride (0.35
mL), and 85% phosphoric acid was added to the flask in that order of addition. A magnetic stir bar
was added to the flask. Solution was stirred and heated for 10 minutes. Flask was removed and
allowed to cool to ambient temperature. DI water (0.5 mL) was added and the solution was cooled
to 0°C by ice bath. The solution was neutralized with 3M sodium hydroxide dropwise while stirring
and cooling. PH was monitor by pH indictor paper. Solid product was isolated by vacuum ... Show
The yellow band, ferrocene, elute from the column with the like non–polar phases of hexanes.
Theoretically speaking an additional orange band, representing acetylferrocene, should have eluted
after the shift in mobile phases. Considering that the mobile phase changes from a non–polar content
to that of higher polarity with the addition of ethyl acetate, it is logical that a polar species like
acetylferrocene would elute. After collecting and evaporating the solvent portion of the darkest
yellow fraction, the resulting mass was 0.017 g, an 18% yield from the starting the amount. This
yield could be raise if the additional yellow fractions were collect. The melting point of this
collected fraction was 170°C, which reasonably close to the literature value of 172. Considering that
the species sampled was the started reactant, thus there was no chemical change, it safe to assume
the purified product is

Electrophilic Aromatic Substitution Formal Lab Essay
Electrophilic Aromatic Substitution
Objective
The objective of this experiment was to illustrate electrophilic aromatic substitution by synthesizing
p–nitroanilide (as well as ortho) from acetanilide by nitration. The para form was separated from the
ortho form based on solubility properties using recrystallization techniques.
Synthetic equations:
Physical Properties & Hazards of Reagents/Products: (all taken from Sigma–Aldrich website)
Acetanilide
MM = 135.16 g/mol
Melting point = 113–115°C
Hazards: acute toxicity
Sulfuric acid
MM = 98.08 g/mol
Boiling point = 290°C
Density = 1.840 g/mL
Hazards: corrosive to metals and skin, serious eye damage
Nitric acid
MM = 63.01 g/mol
Boiling point = 120.5°C
Density = ... Show more content on Helpwriting.net ...
Discussion Aromatic compounds can undergo electrophilic substitution reactions. In these reactions,
the aromatic ring acts as a nucleophile (an electron pair donor) and reacts with an electrophilic
reagent (an electron pair acceptor) resulting in the replacement of a hydrogen on the aromatic ring
with the electrophile. Due to the fact that the conjugated 6π–electron system of the aromatic ring is
so stable, the carbocation intermediate loses a proton to sustain the aromatic ring rather than reacting
with a nucleophile. Ring substituents strongly influence the rate and position of electrophilic attack.
Electron–donating groups on the benzene ring speed up the substitution process by stabilizing the
carbocation intermediate. Electron–withdrawing groups, however, slow down the aromatic
substitution because formation of the carbocation intermediate is more difficult. The electron–
withdrawing group withdraws electron density from a species that is already positively charged
making it very electron deficient. Therefore, electron–donating groups are considered to be

"activating" and electron–withdrawing groups are "deactivating". Activating substituents direct
incoming groups to either the "ortho" or "para" positions. Deactivating substituents, with the
exception of the halogens, direct incoming groups to the "meta" position. The experiment described
above was an example of a specific electrophilic aromatic

Aromaticity Of Pyridine Lab Report
Aromaticity and reactions of pyridine Introduction
Pyridine is a nitrogen containing aromatic analogue of benzene. The N in pyridine is sigma bonded
to two atoms and has a lone pair, and is therefore sp2 hybridized.
This leaves one electron in an unhybridized p orbital, which contributes to the system, making a
total of 6, and therefore an aromatic molecule (5 x C–H contribute 5 electrons, N contributes 1, = 6,
4N+2). The lone pair on the N is in an sp2 orbital, which means it is directed away from the ring but
in the same plane.
The lone pair of electrons are not involved in the aromatic system, and stick out away from the
molecule.
Pyridine is aromatic, and displays aromatic characteristics such as high resonance energy
(27kcal/mol), ... Show more content on Helpwriting.net ...
Hellwinkel, D. (1998). Die systematische Nomenklatur der Organischen Chemie (4th ed.). Berlin:
Springer. p. 45. ISBN 3–540–63221–2.
2. Gossauer, A. (2006). Struktur und Reaktivität der Biomoleküle. Weinheim: Wiley–VCH. p. 488.
ISBN 3–906390–29–2.
3. Curvall, Margareta; Enzell, Curt R.; Pettersson, Bertil (1984). "An evaluation of the utility of four
in vitro short term tests for predicting the cytotoxicity of individual compounds derived from
tobacco smoke". Cell Biology and Toxicology. .
4. Aeschbacher, HU; Wolleb, U; Löliger, J; Spadone, JC; Liardon, R (1989). "Contribution of coffee
aroma constituents to the mutagenicity of coffee". Food and Chemical Toxicology. 27 (4): 227–232.
doi:10.1016/0278–6915(89)90160–9. PMID

Lab Report On Nitroacetanilide
Electrophilic Aromatic Substitution:
Date Performed: 10/26/17–11/2/17
Experimenter: James Settles
Date: 11/6/17
Drawer: 11V
Objective: The objective of this experiment was to perform experiment that would nitrate
Acetanilide and produce Nitroacetanilide, then also separate the para–directing and ortho–directing
products of Nitroacetanilide by an electrophilic aromatic substitution by means of filtration and
recrystallization. This lab also demonstrated how electrophilic aromatic substitution works with
activating and deactivating groups.
Physical Properties and Hazards:
Synthetic Equation: Acetanilide reacts Nitronium to form O–Nitroacetanilide and P–
Nitroacetanilide.
Figure A. Structure of Acetanilide ... Show more content on Helpwriting.net ...
The solid was collected by vacuum filtration. A thin layer chromatography was run on the crude
solid, the recrystallized solid and the filtrate from the recrystallization. The solid was dried until the
next lab period, and was then weighed and a melting point was taken. For the TLC analysis 3 x's
were drawn on the bottom portion of a TLC plate for the origins. A small amount of the crude
Nitroacetanilide was dissolved in warm ethanol and spotted on the TLC plate. A small amount of the
recrystallized Nitroacetanilide was dissolved in warm ethanol and spotted on the same TLC plate,
and the same was done for the filtrate. A UV lamp was used to ensure that the right amount of
sample was being used, then the plate was eluted in ethyl acetate. The plate was removed when the
solvent had reached about 3⁄4 of the way to the top. The solvent was marked with the UV lamp, and
the spots were circled to record in the lab notebook.
Calculations:
Theoretical yield of Nitroacetanilide:
Yield = Theoretical mass of Nitroacetanilide= 1.34 g Nitroacetanilide Actual mass of
Nitroacetanilide obtained: 0.15 g Nitroacetanilide
Percent Yield = () x 100% = () x 100%= 11.2% Nitroacetanilide Recovered
1) Crude Product: (Both Ortho– and Para– Products)
Higher spot: () = 0.927 = Rf
Middle spot: () = 0.673 = Rf

Lower spot: () = 0.491 = Rf
2) Recrystallized: (Para– Product)
() = 0.473 = Rf
3) Filtrate: (Ortho– Product)
Higher spot: ()

Does Nitric Acid Affect The Synthesis Of Nitroacetanilide
In this experiment, nitric acid and sulfuric acid were mixed to form nitronium ions, hydronium ions,
and hydrogen sulfate ions. The amide on the acetanilide is an electron donating group, an activator,
which means that when an activated electrophile is added to the acetanilide, it will add in the ortho,
para positions. In this case, the activated electrophile is the nitronium ions, which react with the
acetanilide and form an arenium ion. Then, the hydrogen sulfate ions pull off the hydrogen that is
attached to the same carbon as the nitronium ion, allowing the lone pair that is now on the carbon
the hydrogen left from to form a double bond with the electron deficient (positively charged) carbon
next to it. The products formed are the ortho and para–substitutions of nitroacetanilide. ... Show
The crude solid was dissolved in hot ethanol and then, was allowed to cool. As the solution cooled
the solubility of the compounds in the solution drops, which allowed the nitroacetanilide to
recrystallize from the solution. The size of the crystals depends on the rate of cooling; a slower
cooling rate leads to the formation of larger crystals. In order to collect the crude solid and the
recrystallized solid, vacuum filtration was used. Vacuum filtration uses reduced pressure to force the
solution and air through the filter paper, allowing for the solid to

Electrophilic Aromatic Iodination of Vanillin
Electrophilic Aromatic Iodination of Vanillin Purpose: The purpose of this laboratory experiment is
for an aromatic compound to undergo an electrophilic substitution reaction. To carry this out, our
method combines sodium iodide and common bleach as the oxidizing agent in aqueous alcohol as
the solvent. Balanced Chemical Equations: Physical Properties: Name of Chemical Chemical
Structure Molar Mass (g/mol) BP/MP (ºC) Density (g/mL) Mass/Vol. Used Purpose 3–methoxy–4–
hydroxybenzaldehye C8H8O3 152.1494 MP=81–83, BP=285 NA 0.1g Solute Ethanol CH3CH2OH
46.0688 MP=–114.1, BP=78.3 0.789 2.0mL Solvent Sodium Iodide NaI 149.8943 MP=661,
BP=1300 3.667 0.117g Catalyst Bleach NaOCl 74.4422 MP=NA, BP=40dec 1.209 1.1mL
Oxidizing ... Show more content on Helpwriting.net ...
Using the ethanol as the solvent produces a more environmentally favorable conditions, and the
bleach combined with sodium iodide produces an efficient and selective (mono–) product. Once the
final product had been recrystallized with isopropanol, the crystal were collected via vacuum
filtration. These crystals took some time to dry out, but they eventually were dry enough to scrape
out for further evaluation. After an IR was run, it was quite obvious the product was surely
Iodovanillin. Further analysis of the melting point was taken to ensure the final product was the
desired Iodovanillin. A few sources of potential error are as follows: loss of product on glassware
throughout the experiment, inadequate measuring of chemicals, "impure" chemicals being worked
with, and loss of final product during crystallization processes. Questions: 1. The HC=O is a
deactivating substituent that is moderately deactivating and meta directing, the –OCH3 is an
activating substituent that is strongly activating and ortho/para directing, and the –OH is an
activating substituent that is strongly activating and ortho/para directing. 2. The purpose of the
thiosulfate in this reaction is the pH testing of bleach substances. If one first adds sodium thiosulfate
to such solutions, it will neutralize the color–removing effects of bleach and allow one to test the pH
of bleach solutions with liquid

Post-Lab Questions
Post–Lab Questions
Pages 524 – 528
3. a. Since the pKa value of sulfuric acid (–3) is smaller than that for nitric acid (–1.3), sulfuric acid
is a stronger acid.
b. The chemical equation for the equilibrium involving the reaction of sulfuric and nitric acids is as
follows:
H2SO4 (aq) + HNO3 (aq) HSO4– (aq) + H2NO3+ (aq)
c. Calculations used to determine the value of Keq for the acid–base reaction in Part b are as
follows:
Keq = (Ka1) x (1 / Ka2)
Keq = (103) x (1 / 1013)
Keq = 10–10
7. The nitro and bromo groups of these molecules are both electron withdrawing. Additionally, the
bond between these groups and the benzene ring will be polar. In 4–bromonitrobenzene, the dipole
moments caused by the nitro and bromo groups are in opposite directions, resulting in their
cancellation to some extent. As a result, the dipole moment of the ... Show more content on
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Upon decreasing the temperature of the reaction, the fraction of molecules having an energy equal to
the action enthalpy decreases; hence, the rate of the reaction decreases. So at lower temperatures, the
time required for an electrophilic substitution reaction of different activated aromatic systems will
differ to a greater extent. This allows for an easier method to study the kinetics of a reaction for such
systems. Thus, the concept of performing some SE2 reactions at 0 C decreasing the rate of the
reaction allows for the determination of the order of reactivity more definitively.
6. Chlorine is more electronegative than bromine. As a result, Cl2 is a much stronger electrophile
than Br2. The halogenation of an arene is an aromatic electrophilic substitution. The rate and
enthalpy of activation of this reaction depends on the nucleophilicity of the arene and
electrophilicity of the electrophile. The greater the electrophilicity of the electrophile, the lower the
enthalpy of activation for the reaction and the greater the rate will be. Thus, the relative rate of SE2
reactions will be faster if Cl2 were used instead of

Nitration of Methyl Benzoate
NITRATION OF METHYL BENZOATE Purpose: The main objective of this experiment was to
synthesize methyl nitrobenzoate from methyl benzoate, using the mixture of nitric and sulfuric acid
by performing the process of electrophillic aromatic substitution. During this reaction, the
combination of HNO3 and H2SO4 made a nitrating solution. The crystallization was done to
accomplish pure product. The melting point and Thin Layer Chromatography (TLC) were
performed to test the purity of the product. Using the methyl benzoate reaction product, methyl
nitrobenzoate, one can determine the meta–substituted, para–substituted and orthosubstituted of the
final products. Furthermore, HNMR and IR used to investigate the quality of the product. ... Show
This would indicate that during the recrystallization there was a reduction in the percentage yield of
the production. The obtained final product melting point rang was 76.2–780C. This would show that
the experimental melting point was very close to the literature value of 78 – 80°C which denotes
the meta–substituted of the product. So, the analysis of the melting point confirmed that the product
was methyl meta–nitrobenzoate as it was anticipated. Additionally, use of the melting point analysis
shows that –NO2 group could be added to the methyl benzoate at the meta position successfully.
The ortho– and para products could have been also analyzed during the experiment; however, they
were not chosen for the product (methyl benzoate) because they have unstable resonance forms that
have positive charges near one another. The two positive charges that are next to one another can
make the product to be unstable and as result ortho– and para– substituted products are not favorable
in this electrophilic aromatic substitution reaction. Also, an IR of the product confirmed that methyl
m–nitrobenzoate as a favorable. A peak located at 1536.1cm showed of the Aromatic C=C. At the
1351.8cm –1 there is a –1 presence of –NO2. The one located at 1730.1 cm was the result of a
carbonyl group and –1 the peak at 1617.7 cm–1 specified the existence of a benzene ring. Another
peak at 1151.5 cm–1

Acetanilide Reaction Lab Report
In the following experiment, acetanilide was reacted with bromine to yield a para isomer or an ortho
isomer. The electrophile was generated due to glacial acid, as opposed to using the routine solvent,
FeBr3. Glacial acid was used in replacement because acetanilide was a strong activator and FeBr3
would not suffice. It allowed for the bromine atoms to become polarized which allowed for the
reaction to take place. The pi bonds of Benzene ring nucleophilically attacked the polarized bromine
atom and an arenium cation resulted. Resonance allowed for the arenium ion to be stabilized and for
the carbocation to move throughout the ring until it reached the acetanilide substituent containing
the acetamide group. Acetamide groups contain an NH atom ... Show more content on
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The singlet that appeared up field with an integration value of 3 was the Hd peak and its appearance
here was due to the oxygen deshielding it from seeing any other neighbors besides itself. The
protons in the benzene ring were observed to be further downfield due to the benzene ring as
opposed to the proton that is bonded to the nitrogen. The proton bonded to the nitrogen, Hc, was
observed as a singlet around 7.218, which is still downfield. The aromatic protons, Hb and Ha,
showed up as doublets and they can be distinguished by the substituents they are closest to, as these
substituents determine the chemical shifts of Hb and Ha. The protons closest to the acetamide group,
Hb, appeared more upfield and this is because the nitrogen atom donates electrons to the ring that
would allow for Hb to not have its electron drawn as much. The opposite effect are the protons
bonded closest to the bromine substituent and this is because the bromine atom exhibits an electron
withdrawing inductive effect. Because bromine withdraws electron density, Ha would be more
deshielded and thus appear farther downfield than Hb. With that, it is important to note that the
peaks that appeared at 7.250ppm, 1.582 ppm, and 1.244 ppm were contaminants from CDCL3,
water, and ethanol respectively. These contaminants may have found their way into the reaction
mixture during the recrystallization process or during NMR

The And Pka Values Of Nucleobases
NUCLEOSIDE TAUTOMERISM AND pKa VALUES
The nucleophilicity of nucleobases (Figure 2.1.1) is dictated by the pKa of the amino and amido
functions and their tautomeric forms. Table 2.1.1 lists the pKa values of nucleobases. The amide–
like nitrogens (N3 of uridine and N1 of guanosine) are acidic in character, whereas the ring
nitrogens are basic. Therefore, at strongly alkaline pH, the proton at N3 of uridine and thymidine
and that at N1 of guanosine are removed. Under acidic conditions (at pH ~3), the sites of
protonation are N1 of adenosine and N3 of cytidine. At more acidic pH, the N7 of guanosine and
adenosine and the O4 of uridine are protonated. Thus, all the bases remain mostly uncharged in the
physiological range of pH 5 to 9 ... Show more content on Helpwriting.net ...
Quite clearly, protecting groups and the protocols for their installation and removal should be
designed to avoid various side reactions.
Nucleobases undergo substitution reactions with electrophilic reagents. For example, both N– and
O–alkylation of the imide and lactam groups occur with alkylating agents. The N7 position of
purines is also a potential site for electrophilic attack (Figure 2.1.5). Because of these competing
reactions, simple alkylation of exocyclic amino function is not a viable protection strategy for
nucleobases. On the other hand, it is possible to chemoselectively acylate the exocyclic amino
group. Thus, acyl–type protecting groups are widely used for the protection of the exocyclic amino
groups of nucleosides (Figure 2.1.7).
The imide/lactam NH of thymidine, uridine (pKa, 9.38), and guanosine (pKa, 9.42) is weakly acidic
and can deprotonate under basic conditions. The resulting nucleophilic anion can react with a variety
of reagents such as activated phosphates, dicyclohexylcarbodiimide (DCC), mesitylene sulfonyl
chloride, 1–(mesitylene–2–sulfonyl)–3–nitro–1,2,4–triazole (MSNT), acid chlorides,
phosphitylating reagents, and electrophilic reagents that are employed during coupling reactions.
These side reactions result in nucleobase–derived N– and O–products.
Nucleosides also react with a variety of nucleophilic reagents. For example,

Essay Preparation of 4-Bromoaniline
Preparation of 4–bromoaniline
Introduction
Aromatic compounds tend to undergo electrophilic aromatic substitutions rather than addition
reactions. Substitution of a new group for a hydrogen atom takes place via a resonance–stabilized
carbocation. As the benzene ring is quite electron–rich, it almost always behaves as a nucleophile in
a reaction which means the substitution on benzene occurs by the addition of an electrophile.
Substituted benzenes tend to react at predictable positions. Alkyl groups and other electron–donating
substituents enhance substitution and direct it toward the ortho and para positions. Electron–
withdrawing substituents slow the substitution and direct it toward the meta positions.
Aromatic compounds also undergo ... Show more content on Helpwriting.net ...
Aniline 93.1 10 0.107 Yes
Ethanoic anhydride 102.1 12 0.118 No
Glacial ethanoic acid 60.1 25 0.416 No
No. moles produced by aniline = 0.107 moles
Theoretical mass of N–phenylethanamide = n*MR = 0.107 × 135 = 14.44g
Percentage yield = actual yield (g)/theoretical yield (g) × 100 = (11.9/14.44) × 100 = 82%
For preparation of N–(4–bromophenyl) ethanamide:
Product RMM Volume used/ g Volume used/ mL Moles used Limiting reagent?
N–phenylethanamide 135.2 5 0.0370 No
Bromine 159.8 2.1 0.0131 Yes
No. moles produced by bromine = 0.0131 moles
Theoretical mass of N–(4–bromophenyl) ethanamide = n*MR = 0.0131 × 159.8 = 2.10 g
For preparation of 4–bromoaniline:
Product RMM Volume used/ g Volume used/ mL Moles used Limiting reagent?
N–(4–bromophenyl) ethanamide 214.1 5 0.0234 Yes
Hydrochloric acid 36 50 5.00 No
No. moles produced by N–(4–bromophenyl) ethanamide = 0.0234 moles
Theoretical mass of 4–bromoaniline= n*MR = 0.0234 × 214.1 = 5.01 g

Discussion
The preparation of N–phenylethanamide from aniline was the first step of the experiment.

Aromatic Substation
Aromatic substances are cyclic and planar molecules with resonances bonds that exhibit molecular
stability. Most aromatic substances are a derivative of a benzene ( aromatic hydrocarbon) ring. The
structure of aromatic substances is defined by the cylic overlapping sp2 hybridized atoms, figure 1.
Benzene rings are nonpolar, insoluble in water and very stable due to the delocalized pi– electrons.
This stability of benzene rings means that no many reactions can occur with some aromatic
substances. There are a few substitution reactions in an aromatic substances replaces a hydrogen
within a functional group(s). Aromatic substation occurs when an electrophile replaces a hydrogen
on a benzene ring. In aromatic substation, the aromatic ring attacks an electrophilic molecule. This
causes the double bond between two carbons to break, leaving one carbon with the electrophilic
attachment and the other becomes a carbocation. Due to the carbocation, the aromatic ring is not
stable, and requires the replacement of that double bond. The nucleophile in the solvent will grab the
hydrogen on the carbon with the attached electrophile. The electrons from that hydrogen will reform
the double between the carbocation and ... Show more content on Helpwriting.net ...
Meta indicates two electrophiles on the first and third carbon and para is the first and fourth carbon.
For this lab Ortho–para directors where the focus due to activation. Activation is the process by
which activating substituent groups a stabilize the cationic intermediate after the addition of the first
electrophile substituents. Activating substituents donate electrons to the cationic intermediate to
stabilize the ring. The extra electrons are stored only on carbons 2,4 and 6, hence ortho–para
directing of the second electrophilic substituent. Depending on the strength of the activator one or
two electrophilic substituents may be added to the benzene

Lewis–Acid Catalyzed electrophilic aromatic substitution reactions of thionyl chloride, and benzene.
Introduction: Organic sulfoxides, especially diphenyl sulfoxide (Ph2SO), are useful synthetic
reagents (Kaczorowska et al., p. 8315). Diphenyl sulfoxide has been used in catalytic oxidation of
alkyl sulfides to sulfoxides (Arterburn & Nelson, p.2260). They also play an important role as
therapeutic agents. Examples include anti–ulcer, antibacterial, antifungal, anti–therosclerotic,
anthelmintic, antihypertensive, and cardiotonic agents, as well as, psychotonics and vasodilators
(Kaczorowska et al., p. 8315). Diphenyl sulfoxide is also used as a reagent in the formation of
glycosidic bonds (Garcia, Pool, & Gin, p.1). This involves an in situ ... Show more content on
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8315). Furthermore, the organic sulfoxides have an important function as therapeutic agents and
these include: anti–ulcer, antibacterial, antifungal, and cardiotonic agents, as well as, psychotonics
and vasodilators (Kaczorowska et al., p.8315). Examining these various reactions, which produce
sulfoxides, will be important for educational purposes: providing alternate ways to obtain
sulfoxides, and to distribute more knowledge on Lewis–Acid catalysts and their interaction in EAS
reactions. Lewis–acids are an important class of acids and are imperative for adolescents and even
adults, who are in schooling, to learn

Synthesis Of Pnitroaniline From Aniline Essay
This experiment takes a longer time then other experiments, taking approximately three weeks to
complete. It involves a three–step synthesis to make pnitroaniline from aniline and then we will be
characterizing our product using the new and useful technique of thin layer chromatography (TLC).
We will not be doing the first part of this experiment only parts two and three.
Electrophiles are reagents which are attracted to other electrons and in order to bond to nucleophiles,
they accept electron pairs. Electrophiles attack benzene and this results in hydrogen substitution.
Nonetheless, this isn't thermodynamically favoured due to a sp3 hybridized carbon being generated.
This disrupts the cyclic conjugation. In order for the aromatic ring to be regenerated, a proton will
be lost at the sp3 hybridized carbon. This means pnitroaniline can be prepared by electrophilic
aromatic substitution. ... Show more content on Helpwriting.net ...
Acetyl groups are electron withdrawing. This reduces the activity of the lone pair on the nitrogen
either in a protonation reaction or an oxidation reaction. The conditions required for nitration are
extremely acidic. Protonation of the nitrogen of aniline causes it to become a very strong
deactivating group.
In the second part of the experiment, we will be performing the nitration of Acetanilide. We will first
need to form the nitronium ion in situ by the dehydration of the nitric acid. The dehydrating agent
for this experiment is sulphuric acid. The nitronium ion is an extremely strong and powerful
electrophile which reacts with π–electrons involved with the aromatic ring of

Aromaticity And Reactions Of Pyridine
Aromaticity and reactions of pyridine Introduction
The structure of pyridine e considerably resembles that of benzene. It may be formally derived from
the structure of benzene through the exchange of one ring carbon for a nitrogen but, is pyridine
which is structurally and electronically allied to benzene, also aromatic?. Pyridine is aromatic based
on the following facts. The protons of pyridine show chemical shifts in the NMR spectrum that are
ordinary of aromatic protons. Furthermore, electrophilic substitutions at pyridine are possible. The
nitrogen of pyridine is sp2–hybridized and possesses one lone electron pair. This electron pair is
located in an sp2 orbital that is parallel to the ring plane. Therefore, in contrast to pyrrole, the
nitrogen 's lone electron pair of pyridine doesn 't take an interest in the aromatic π electron system.
As a result, pyridine can easily be protonated, yielding a pyridinium cation. Two valence electrons
of the nitrogen are included in the two (σ bonds) with the adjacent carbons. The fifth valence
electron of the nitrogen occupies the p orbital that is perpendicular to the ring plane. Thus,
analogous to the ring carbons, this electron takes part in the π electron system. Com¬par¬i¬son of
ben¬zene and pyri¬dine.
Electrophilic substitutions at pyridine
As an aromatic compound, pyridine may participate in electrophilic substitutions as an electrophile.
How easily and at which positions do these substitutions occur? In order to answer

Dichloromethane Lab Report
In this experiment, a Friedel–Crafts acylation was carried our by reacting acetic anhydride (the
acylating agent) and dichloromethane (solvent) with anisole to substitute an acyl group onto the
aromatic ring of anisole. Friedel–Crafts reaction can be classified as an electrophilic aromatic
substitution. This involves an electrophile replacing a hydrogen atom located in the aromatic
compounding forming a new carbon–carbon double blond. Acylation of a monosubstituted benzene
has the opportunity to yield any or all three different disubstituted products. We used the boiling
point and results from 1H NMR spectroscopy to determine if the product was a single product or a
mixture of isomers. Say something about yields, NMR, and boiling point.... ... Show more content
on Helpwriting.net ...
The first step was to weigh 2.93 g of anhydrous AlCl3, which acts as the Lewis acid catalyst. 10 mL
dichloromethane was used as the reaction solvent, and 1 mL anisole were stirred in a 50 mL RBF, in
an ice bath because the reaction is highly exothermic. Next, the previous measured AlCl3 is added
very slowly. Any remaining mixture is washed out with CH2Cl2. 1 mL acetic anhydride, which is
the acylating agent, is dropped slowly through the funnel because an exothermic reaction occurs. It
is then heated under reflux with a drying tube to exclude moisture from the reaction for 30 minutes
to complete the reaction. The warm mixture is now poured over 10 g of ice in a beaker to
decompose the aluminum chloride complex of the product and transfer organic salts to the aqueous
phase. The product was then allowed to sit at room temperature for one week. The organic layer was
then collected and washed with 5 mL 3 M NaOH and 5 mL saturated aqueous NaCl in the second
wash. The organic is the bottom layer both times due to the density of the halogen present in the
dichloromethane. The CH2Cl2 was then dried using ~1 g of anhydrous MgSO4, a drying agent. I
continued to add more drying agent until there was no clumping and the solution had free–floaters.
The dichloromethane layer was evaporated by the Rotovap in a 50 mL round bottom flask

Nucleophilic Aromatic Substitution of...
Experiment #1 Nucleophilic Aromatic Substitution of 2,4–dinitrochlorobenze Name: Anouk Deck–
Leger Student I.D: 9380868 Date performed: September 13th, 2010 Due Date: September 20th,
2010 Introduction: The company DNCB produces large amounts of 2,4–dinitrochlorobenzene and
they sell this product to treat against warts and severe and chronic hair loss. It can also be used as an
alternative treatment for HIV. The supervisor notices an excess amount of m–aminobenzoic acid
stored away which is currently not being used for anything. This reactant can be used in certain
reactions to produce valuable solutions for ophthalmologists. This product is going to waste, and our
objective is to see if we can obtain a usable end product when ... Show more content on
Helpwriting.net ...
FT–IR spectrum The major peaks are C=O, O–H, N–H, C=C, and NO2.1 A peak between 1660 and
1820 cm–1 (presence of C–O) and a broad peak between 2400 and 3400cm–1 (presence of O–H)
indicates the presence of carboxylic acid (COOH). In this graph there is a peak at 3248 cm–1 (C–O)
and a peak at 1589 cm–1 (O–H) which confirms the presence of carboxylic acid. To confirm the
presence of amides, a medium absorption near 3400 cm–1 should be observed which is the case in
this graph. Absorptions in the region of 1450 to 1600 cm–1 often designate an aromatic ring and
when consulting the C–H region we can confirm its aromatic since the peak is to the left of the 3000
cm–1. Nitro groups give two strong absorptions at 1530–1600 cm–1 and 1300–1390 cm–1. H NMR
spectrum Nuclei tend to be deshielded by groups which withdraw electron density. Deshielded
nuclei resonate at higher δ values, whereas shielded nuclei resonate at lower δ values.Examples of
electron withdrawing substituents are –OH, –OCOR, –OR, –NO2 and halogens. Discussion: We
began this experiment by weighing out the known values of mass for 1–chloro–2,4–dinitrobenzene
and m–aminobenzoic acid which was 1.012g and 0.686g respectively. These values were calculated
before the experiement based on the mole ratios of the balanced equation in question. Here the
reaction was a 1:1 ratio so we were able to determine the theoretical mass of our product, m–(2,4–
dinitroanilino)

Sodium Iodide Lab Report
1. Sodium Iodide is not an electrophilic source for Iodine because Iodine is the least reactive of all
the halogens, and it itself does not serve as a base, due to its positive charge. This means that
Sodium Iodide needs an Oxidizing agent to make it a strong electrophile.
2. Sodium Hypochlorite is an oxidizing agent for Sodium Iodide, which in turn contributes a strong,
electrophilic Iodide atom to the aromatic ring in the final product. The mixture was orange/red,
indicating the two substances added, then the mixture changed to a pale yellow indicating that the
reaction started, and a precipitate formed, indicating that the Iodine attached to the Salicylamide,
and the reaction was complete.
3. It was necessary to add Sodium thiosulfate at the end of the reaction, because Sodium thiosulfate
remove any excess Iodine ions in that it reduces the ions to Sodium Iodide and stops the reaction, to
prevent any more electrophilic substitution.
4. ... Show more content on Helpwriting.net ...
The iodination of O–acetylsalicylamide under the same conditions of this experiment would be
slower than Salicylamide, because O–acetylsalicylamide has an amine group, a carboxyl group, and
no hydroxyl group, which means that the sodium hypochlorite solution would not be able to
deprotonate the Hydroxyl group, thus not allowing a solid precipitate to form, and Hydrochloric acid
would not be able to add any Hydrogen atoms due to the Octet rule. The only way that Hydrogen
could be added is by breaking double bonds and stabilization (Resonance). And steric hindrance
would be another key facet slowing the addition of an Iodine ion to the

In this experiment, an electrophilic aromatic substitution reaction was performed through the
addition of a nitro group to bromobenzene. The experiment uses the nitronium ion, NO2+, which
acts as an electrophile to replace a hydrogen atom in the aromatic system of bromobenzene. The
bromine substituent on the benzene introduces the possibility of isomers from the reaction with the
nitronium ion: NO2+ can be positioned in the ortho position (making 1–bromo–2–nitrobenzene), the
meta position (making 1–bromo–3–nitrobenzene), or the para position (making 1–bromo–4–
nitrobenzene). There is also a chance that poly–nitration can occur to produce dinitrobenzene. Since
nitro groups are deactivators, it requires high temperatures to add another nitro group to the benzene
ring. To prevent this poly–substitution from occurring, it is important to control the rate of the
reaction by monitoring the temperature during the reaction (the temperature should not exceed
60oC). By controlling the temperature, there is insufficient ... Show more content on Helpwriting.net
...
Nitric acid, HNO3, does not act as a strong enough electrophile on its own. It needs the assistance of
sulfuric acid, H2SO4. Sulfuric acid, a strong acid, protonates the oxygen that is part of the hydroxy
group on nitric acid to make it a good leaving group. The leaving group (water) departs from the
molecule, leaving the nitronium ion. The nitronium ion is a stronger electrophile than nitric acid and
can nitrate bromobenzene. Bromobenzene was added to the mixture of sulfuric acid and nitric acid
dropwise through a water–cooled condenser to prevent the reaction mixture from overheating.
Overheating of the reaction mixture could lead to poly–substitution. To prevent overheating, the
temperature of the mixture was maintained to be under 55oC. The acid mixture was swirled to make
sure that bromobenzene was being dissolved and to prevent the possibility of

Electrophilic Aromatic Substitution
Mapua Institute of Technology
Organic Chemistry Laboratory 2 Final Report
Factors Affecting the Relative Rates of Electrophilic Aromatic
Substitution Reaction
Justiniano, Priscilla Raiza N.
School of Chemical Engineering and Chemistry, Mapua Institute of Technology, Intramuros,
Manila, Philippines
Experiment No.1, Submitted on August 6, 2011 at N402.
Abstract
EXPERIMENT NUMBER ONE IS ALL ABOUT THE ELECTROPHILIC SUBSTITUTION OF
AROMATIC COMPOUNDS. AROMATIC COMPOUNDS ARE THOSE ORGANIC
COMPOUNDS WHICH HAVE BENZENE RING (CYCLOHEXA–1,3,5–TRIENE). AROMATIC
COMPOUNDS ARE ALWAYS FOLLOWS THE SUBSTITUTION REACTION BECAUSE OF
THE STABILITY OF THE BENZENE RING. IT WILL NOT PROCESS THE ELIMINATION,
ADDITION OR REARRANGEMENT REACTION. ... Show more content on Helpwriting.net ...
b. Chlorobenzene– is an aromatic organic compound with the chemical formula C6H5Cl. This
colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture
of other chemicals.
c. Aspirin– is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an
antipyretic to reduce fever, and as an anti–inflammatory medication.
d. Acetanilide– is an odorless solid chemical of leaf or flake–like appearance. It is also known as N–
phenylacetamide, acetanil, or acetanilide, and was formerly known by the trade name Antifebrin.
e. p–Nitrophenol– is a phenolic compound that has a nitro group at the opposite position of hydroxy
group on the benzene ring.

f. Anisole– is the organic compound with the formula CH3OC6H5. It is a colorless liquid with a
smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial
fragrances. The compound is mainly made synthetically and is a precursor to other synthetic
compounds.
g. Phenol– is an organic compound with the chemical formula C6H5OH. It is a white, crystalline
solid. This functional group consists of a phenyl, bonded to a hydroxyl (–OH).
The Apparatus/ materials used are the following: a. Test tube rack – is used in a laboratory and it is
used to hold/support test tubes containing chemicals waiting for further operations.
b. Hot water bath– is when you

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