Iodination Of Salicylamide Lab Report

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
... Get more on HelpWriting.net ...

Nucleophilic Substitution Reaction Lab Report
Introduction:–. To natural science the substitution responses is the The greater part significant
reactions, particularly Nucleophilic fragrant substitution responses the place nucleophile strike sure
charge alternately incompletely certain accuse Concerning illustration it can so, it replaces An
weaker nucleophile which after that gets to be An abandoning bunch. The remaining sure alternately
incompletely certain particle gets a electrophile. The general type of the response is:. Nuc: + R–LG
→ R–Nuc + LG:. Those electron combine (:) starting with the nucleophile (Nuc :) strike the
substrate (R–LG) framing another covalent bond Nuc–R–LG. The former state about accuse will be
restored The point when the abandoning aggregation (LG) departs for ... Show more content on
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Need simply one step. Those assault of the reagent and the removal of the abandoning bunch happen
all the while. This system generally brings about reversal from claiming setup. On the substrate that
is under nucleophilic strike is chiral, those response will prompt a reversal from claiming its
stereochemistry called a Walden reversal. To a sample (chloromethane for bromide particle. ( SN2
ambush might happen Assuming that the posterior course of ambush is not sterically hindered by
substituents on the substrate. Subsequently this system generally happens during a unhindered
essential carbon focal point. Assuming that there may be steric swarming on the substrate close to
those abandoning group, for example, such that at a tertiary carbon center, those substitution will
include a SN1 as opposed an SN2 mechanism, (an SN1 might Additionally make less averse in this
the event in light a sufficiently stable carbocation go–between Might a chance to be formed). At the
substrate is a fragrant compound those response kind will be nucleophilic fragrant substitution.
Carboxylic corrosive subsidiaries respond for nucleophiles for nucleophilic acyl substitution. This
sort of response camwood a chance to be advantageous in get ready

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 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

Tert-Butyl Chloride Lab Report
The aim of this experiment was to perform a reaction via a Sn1 reaction to prepare tert–Butyl
chloride and test the effectiveness of the reaction by examining the reactivity of the product. To
prepare tert–Butylchloride from tert–Butylalcohol, one must cause a Sn1 reaction to occur. An Sn1
reaction is a monomolecular nucleophilic substitution reaction, meaning that one molecule is
involved in each step of the Sn1 reaction. First, the leaving group leaves. After the leaving group
leaves, the nucleophile has enough room to form a bond with the carbocation. As a result, the
leaving group is replaced by the nucleophile (Michman 2016). In our reaction, the nucleophile is
chlorine and the leaving group is water, which forms after the protonation of hydroxide to form a
better leaving ... Show more content on Helpwriting.net ...
On the other hand, Sn2 reactions are dimolecular nucleophilic substitution reaction; thus, all steps of
the reaction occur simultaneously. Rather than the leaving group leaving and then the nucleophile
attacking, the leaving group begins to break its bond with carbon as the nucleophile begins to form a
bond with the carbon. Sn2 reactions result in an inversion of stereochemistry because the
nucleophile must form its bond with carbon behind the leaving group, since the leaving group is still
partially attacked (Michman 2016). To synthesize tert–Butylchloride we must use an Sn1 reaction
pathway because Sn1 reaction are more stable modes of substitution in tertiary and secondary alkyl
halides and alcohols (Michman 2016). Sn2 reactions are more effective for primary alkyl halides
and alcohols. This is again because tertiary alkyl halide, like tert–Butylalcohol, are very large – the
leaving group must leave first to make room for nucleophile. Still, there are some complications that
come into play when conducting an Sn1

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

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

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

Synthesis Of T-Pentyl Chloride Lab Report
Introduction:
The purpose of this experiment was to synthesize t–pentyl chloride from the reaction of t–pentyl
alcohol and concentrated HCl. This reaction occurred through an SN1 reaction, a unimolecular
nucleophilic substitution reaction. This was a First Order Rate Reaction where the rate of t–pentyl
chloride was dependent only on the concentration of t–pentyl alcohol. After the reaction was
completed, the products were achieved via 3 liquid–liquid extractions and then after by simple
distillation. In the liquid– liquid extractions a solute was transferred from one solvent to another.
Then in the simple distillation the miscible liquids or the solution, was separated by differences in
boiling points. After this the product was determined through infrared spectroscopy.
Procedure:
Isolation of Crude Product
A mixture of 22 ml ... Show more content on Helpwriting.net ...
In the process, extraction and distillation techniques were used. The theoretical amount of t– pentyl
chloride was 17.358g, while 15.78 g was the actual amount produced which gave a percent yield of
90.9%. An error occurred while performing the experiment, the filtered dried product in the
distillation process was placed in the wrong flask. Due to this that part of the experiment had to be
redone and the new filtered product had some aqueous solution in it, which caused the boiling point
to be under the specified temperature. The boiling point then was at 50 ℃ compared with the
expected range of 79– 84 ℃. The IR spectrum used above was from another group's results. The
experimental IR spectrum has more prominent peaks in the 3000 cm–1 range compared to the
expected IR spectrum. Nonetheless, the experimental IR spectrum resembles the expected IR
spectrum in the sense that the peaks are closely around the same wavenumber range. This is
probably due to the product being distilled at the right boiling

Determination Of Nucleophile
Introduction The disassociation of acids in a solution are important when choosing the best
nucleophile to proceed with a nucleophilic substitution. A nucleophile is best described as a
chemical that can give away a pair of electrons to a certain electrophile, and produce a pi bond.
Nucleophiles are stronger as conjugate bases. When a stronger nucleophile is presented, a faster
reaction is observed. Depending on the reaction needed, the nucleophile selection is based on
various factors. If the conjugate acid in the reaction is presented by a high pKa the nucleophilicity of
the nucleophile is needed to be stronger for the dissociation of the acid to occur. In addition,
polarizability is also considered when nucleophilicity is determined. ... Show more content on
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This allows for the fragments of a mixture to be analyzed by counting how many times specific ion
components are passed through the spectrum. The fragments presented m/z were
41,55,57,81,93,107,136. By analyzing the presented data, the molecular ion peak was shown
furthest to the right of the graph at 136 m/z. This piece of information explained that the largest
recorded ion being bromo–1–butane (product) was the ion peak. The data reported is a
representation of the molecular mass of the product. Moreover, the base peak displayed was around
57; however, compared to the molecular ion peak, the base peak theoretically should have been
around 68. Fragments 57 and 81 m/z displayed the product, 57 m/z presented the fragments C_4
H_9 , and 81 m/z identified as Br. These two fragments make up 1– bromobutane. As for the neutral
fragments, the mass lost (m–43) and (m–29) plus the over frequencies before the base peak make up
for the hexane added. The sample was also ran through infrared spectroscopy. The wavenumbers
displayed by the data represented specific functional groups and stretches. Functional groups are
displayed by frequencies on the graph. At 3742.71, this frequency was not clearly as identified, but
could have been and alcohol stretch (O–H). Other frequencies on the graph were 2962.12, 2872.57,
and 1462.31 were possibly presented as –C–H S_P 3 stretches. In addition, another frequency

Reac 714 Studying Sn1 and Sn2 Reactions: Nucleophilic...
REAC 714 Studying SN1 and SN2 Reactions: Nucleophilic Substitution at Saturated Carbon Date
of Experiment: February 6, 2008 Objective: The objective of this laboratory experiment is to study
both SN1 and SN2 reactions. The first part of the lab focuses on synthesizing 1–bromobutane from
1–butanol by using an SN2 mechanism. The obtained product will then be analyzed using infrared
spectroscopy and refractive index. The second part of the lab concentrates on how different factors
influence the rate of SN1 reactions. The factors that will be examined are the leaving group, Br –
versus Cl–; the structure of the alkyl group, 3◦ versus 2◦; and the polarity of the
solvent, 40 percent 2–propanol versus 60 percent 2–propanol. ... Show more content on
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The 2–bromobutane is a crystal–like white layer The final appearance of the 2–bromobutane was a
clear liquid that is transparent Reaction Scheme SN2 Substances Formula Weight, g/mol Weight
Used Moles Used Mole Ratio Melting Point °C Boiling Point °C Density g/mL Solubility (g per 100
mL) Water Ether 1–bromobutane 137 Product N/A 1 to 1 N/A 102 1.276 Not soluble in H2O

Examples Of Action Taken Cost Justification
Action taken Cost justification
Immediate first aid. £20 It would not have taken the ambulance over 25 minutes to land at the scene,
be that as it may anything under 30 minutes yet over 1 minute is adjusted to the cost of 30 minutes,
much else besides 30 minutes yet not as much as a hour is adjusted to the cost of 60 minutes.
Making the area secure and safe. £300 The region must be made secure for the crisis administrations
to touch base at and help the person who is harmed.
Taking the injured person to hospital. £60 The taking the harmed individual to the clinic will take
around 60 minutes 1 hour and 29 minutes, much else besides thirty minutes gets adjusted to the cost
of 60 minutes.
Informing next of kin. £40 It will take around ... Show more content on Helpwriting.net ...
Recruitment of replacement staff £3000 The business needed to enlist staff to supplant the harmed
individual, maybe for long term.
Sanctions and penalties Cost Justifications
Compensation excess £20,000 The harmed individual from staff won't have an ordinary life after his
fingers have been genuinely harmed and most likely supplanted with prosthetic fingers.
Solicitor's fees and legal costs £15,000 They will help the harmed individual from staff through his
battle in court and enable him to pick up an existence as near his past life. They will likewise assist
with printed material.
Staff time dealing with legal issues £3000 Staff will take up their chance rounding out printed
material in the event that they've seen what happened to the harmed individual from staff.
Fines and costs due to criminal proceedings £15,000 Maintenance of the piece of machinery should
have been kept up to date.
Annual increase in insurance premiums £20,000 The organizations protection will increment
definitely because of the episode that happened.
The cost of the accident will be £41430. This was contained £4560 for simply dealing with the
accident. This figure was involved £40 for the quick move made by the primary aide. One and just
hour was required by the primary aide to get paid. £850 was expected to call some person to admit
all up the locale the event happened

Alkyl Halides
In this lab, the experimenters will determine how the structure of an alkyl halide (i.e. methyl,
primary, secondary, or tertiary), steric effects, nature of a leaving group, and solvent polarity affect
the relative rates of SN1 and SN2 reactions. In addition, comparing the rates of reactions under
varying concentrations of alkyl halides and nucleophiles will help determine the rate laws for both
types of nucleophilic substitution reactions. During SN2 reactions, a good nucleophile, like iodide,
will displace the leaving group on an alkyl halide in a single step that results in an inversion of
configuration. Methyl, primary, and some secondary halides undergo this bimolecular substitution
reaction. Minimal steric effects combined with a good leaving group and a polar, aprotic solvent ...
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The more stable the resulting carbocation, the quicker this step occurs. After this rate–limiting step,
rapid reaction with a weak nucleophile (e.g. ethanol) attacking from either side of the carbocation
completes the substitution reaction. A racemic mixture forms with a slight favoring of the inverted
molecule because of ion pair formation. A good leaving group capable of delocalizing a negative
charge aids in the formation of the initial carbocation. Additionally, polar, protic solvents capable of
solvating and stabilizing a carbocation support the SN1 mechanism. Tertiary alkyl halides provide
the ideal substrate for the formation of a stable tertiary carbocation that favors the SN1 mechanisms.
When testing the factors affecting the SN2 reaction below, the experimenters will achieve the fastest
reaction when using a primary alkyl halide with minimal branching and the best leaving group (i.e.
1–bromobutane). Varying the concentrations of the alkyl halide or nucleophile while keeping the
other constant will change the rate of reaction for the SN2 reaction. The fastest SN1 reaction will
occur for the tertiary alkyl halide with the strongest leaving group reacted in pure

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

Substitution Reaction of Molybdenum Hexacarbonyl: the Use...
School of Chemistry @ Pietermaritzburg University of KwaZulu Natal Chemistry 310 Substitution
reaction of Molybdenum Hexacarbonyl: the use of infrared spectroscopy as a structural tool in metal
carbonyl chemistry. Abstract The synthesis of isomer A and B of [Mo(CO)4(PPh3)2] were prepared
from molybdenum hexacarbonyl, sodium borohydride and triphenylphosphine with a % yield of
79% and 8.5% respectively. Two isomer was identified using IR spectra and from isomer A four
C≡O stretching was observed, while in isomer B only one C≡O stretching was observed in a
frequency ranged of (1867.24– 2024,39 cm–1) and 1880.91 cm–1 through this results isomer A
concluded to be cis and B to be trans isomer . Results ... Show more content on Helpwriting.net ...
| | |% Yield = (Mass Produced/Theoretical Mass) × 100 | | |= (1.102 g ÷ 1.387g) × 100 | | |= 79 % | | | |
| Table 1: Infrared spectra measure the data for Isomer A and B(nujol mulls) |Isomer |Frequency cm–
1 |Assignment | |A |1867.24 |CO | | |1886.48 |CO | | |1919.66 |CO | | |2024.39

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

In this experiment, a nucleophilic substitution was performed, where a chloride nucleophile
substituted a tertiary hydroxyl group on 2–methyl–2–butanol. In a nucleophilic substitution reaction,
an electron rich nucleophile attacks a positively or partially positively charged electrophile, and
replaces a leaving group. In this reaction, chloride ions are the nucleophile, the tertiary carbon in 2–
methyl–2–butanol is the electrophile, and water is the leaving group.
In the mechanism for this reaction, the oxygen from the hydroxyl group of the 2–methyl–2–butanol
attacks the hydrogen of the HCl, causing heterolytic cleavage of the HCl, resulting in a chloride ion,
and in the oxygen bonding to an extra hydrogen, and becoming positively charged. This changes the
leaving group from a hydroxyl to a water, which is a far more stable leaving group. The leaving
group leaves the hydrocarbon chain through heterolytic cleavage, creating a water molecule, ...
While a technique like gas chromatography could have been used, for this experiment, halide tests
and IR spectroscopy were used to identify the product. Halide tests are an old fashioned test that can
be used to confirm the identity and connectivity of the functional group using various substitution
reactions. In this experiment, NaI and AgNO3 were used, which produce a precipitate if a chloride
functional group is present. The NaI reaction produces a yellow precipitate, whereas the AgNO3
reaction produces a white precipitate. Both reactions involved the chloride group being substituted
by a different nucleophile, in this case, iodide or nitrate. NaI supports an SN2 reaction, which favors
primary carbons, whereas AgNO3 undergoes an SN1 reaction, which favors tertiary carbons. Hence,
depending on which one of these precipitates formed at a faster rate, one could determine if the
carbocation was primary or

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

Synthesis Of Tert-Butyl Chloride Lab Report
The objective surrounding the experiment outlined by this report is to perform an SN1 reaction to
synthesize tert–butyl chloride while recording the reactivity of the compound with sodium iodide
and silver nitrate reagents. Nucleophilic substitution reactions, denoted SN1 or SN2, are
characterized by a nucleophile (electron pair donor) reacting with an electrophile (electron pair
acceptor) to break a bond at a carbon to form a new bond with that carbon.1 In order for the reaction
to take place, a compound or element must break away from the electrophile, so it may accept
electrons from the nucleophile.2 The octet rule must not be disobeyed and thus, the leaving group
allows space for other electrons to attach. Figure 1.1 (right) shows a typical ... Show more content
on Helpwriting.net ...
For this experiment, the nucleophile will be considered the chloride ion from HCl. The chloride ion
in this case constitutes a good nucleophile because it is charged with a 1– and is relatively low in
electronegativity.5 Since the chloride ion will be donating a pair of its electrons, the fact that it is
negatively charge indicates that it indeed has extra electrons to donate and thus its nucleophilic
character is greater as a result. Additionally, the electronegativity of the chloride ion is a showing of
how willing the ion is to donate elctrons, or rather how tightly the chloride ion holds those electrons
to the nucleus. A low electronegativity indicates that the ion is larger in size and allows electrons to
float more freely and also donates those outer electrons more

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

The purpose of this experiment was to perform a nucleophilic substitution reaction to construct a
biologically active compound from two simple parts and then to recrystallize the product collected,
which is a purification technique that purifies solids based on differences in solubility. In order to
accomplish this, other techniques such as heating at reflux, and suction filtration were used. Heating
at reflux is a technique used in lab that allows a solution to be heated for a certain amount of time
once it begins boiling. Suction filtration is a separation technique that is combined with a water
aspirator and was used to collect the product from this experiment, which was 2–
methylphenooxyacetic acid. Reaction Scheme: (Draw reaction scheme here) In this ... Show more
content on Helpwriting.net ...
Upon the addition of water, it was noted that a layer separation occurred and the water layer
remained on top, with the 2–methylphenol layer on the bottom layer. Then, conversion calculations
were performed to determine the appropriate amount of 3M NaOH to be added to the 2–
methylphenol solution. From the calculations, it was determined that 1.08 mL were to be added. 3M
NaOH itself was a cloudy solution in appearance and upon the addition of 3M NaOH to the 2–
methylphenol solution, it was noted a color change occurred and it became a yellow–green solution.
Following this, the same calculations used previously, were used to determine the appropriate
amount of sodium chloroacetate, which was found to be 0.38 g (3.26 mmol). Sodium choloroacetate
was a white, crushed solid that was then combined with 1 mL of water and was swirled until the
sodium chloroacetate completely dissolved. This sodium choloracetate solution was then transferred
to the 2–methylphenol solution by the use of a medicine

Substitution And Elimination Reaction Lab Report
Substitution and Elimination Reactions Substitution reactions replace a functional group with a new
group. These reactions compete with elimination reactions in which a group is eliminated and a π
(pi) bond is formed. Substitution reactions occur when a nucleophile is added to an
electrophile/substrate. Elimination reactions occur when a base is added to an electrophile/substrate.
The electrophile must contain a leaving group to be considered a substrate. Alkyl Halides Alkyl
Halides are the common substrate used in substitution and elimination reactions. Alkyl Halides are
halogen containing alkane compounds. These compounds are commonly used as the electrophile in
substitution reactions. Naming Alkyl Halides is similar to naming alkanes. Halogen substituents are
named just like alkane substituents, for example if there is a chlorine attached to an ethane the
chlorine substituent will be named using the word chloro–. The other halogens are named using the
words flouro–, bromo–, and iodo– respectively. These possible substituents are listed alphabetically
along with the alkane substituents. When dealing with alkyl halides it is important to note that the
carbons attached to the halogens and the carbons attached to those carbons are involved in the
reaction process, therefore we designate these carbons with special symbols to differentiate them
from the rest of the molecule. The carbon atom that is bonded to the halogen is designated the α
(alpha) carbon. The carbons that are

A Study On Molecular Studies
Cyclopropenyl cation (1), the smallest hydrocarbon molecule is a centro–symmetric molecule with a
D_3h symmetry. It's the simplest aromatic species demonstrating aromatic features linked to the
delocalization of the two π electrons. It follows the Hückel's rule, (4n+2) π electron with n = 0.
Aromaticity cannot directly be experimentally measured. However, various methods were
performed such as computational studies from the Schleyer group^1, which address the energy,
structural changes and magnetic properties of cyclic conjugated system.
Computational studies were performed using the Gaussian 94 computational package with ab initio
method and the complete basis set amended by Peterson and co–workers was used for
calculations.^2 The ... Show more content on Helpwriting.net ...
〖〖(CH)〗_3〗^++cyclopropane →cyclopropyl cation (1)
Reaction
Different substituents have different effects on the stability of 1. Effect of these substituents were
studied on the relative stability of 1. Either these substituents have an electron withdrawing effect or
electron donating effect on the ring. Electron withdrawing group such as trialkylsilyl groups
attached directly to the carbenium ion centre have a destabilizing effect. However,
tris(trimethylsilyl)cyclopropenylium hexachloroantimonate (2) could be synthesize from readily
available materials as shown in figure 2 and it's relatively stable.^4
As shown in figure 3, C–C bond lengths for the tris(trimethylsilyl)cyclopropenylium cation are not
equal. The ring is significantly distorted from its ideal D_3h symmetry since one of the carbon
atoms in the ring system is close to the chlorine atoms in the hexachloroantimonate. This distortion
shows that it is caused by the counterion and lattice effects.^4 Using the isodesmic hydride transfer
reaction, the effect of trisilyl and trismethyl substitution was calculated. Three sillyl groups stabilize
1 by 22.4 kcal/mol while three methyl groups has a larger effect and more stable than 1 by 31.4
kcal/mol. Thus, Me > Si >>H was found as the order of the

Nucleophilic Substitution Lab Report
Nucleophilic aliphatic substitution is the substitution of one functional group for another functional
group. The substitution is made at a saturated carbon atom. A saturated carbon is a carbon atom that
is sp3–hybridized. For a compound to be considered a nucleophile they must possess certain
properties. Nucleophiles must contain at least one pair of non–bonding electrons and be neutral or
have a negative charge. Through nucleophilic substitution the non–bonding electrons are donated to
the electrophile. The leaving group can also be either neutral or have a negative charge. Said leaving
group must also accept a pair of bonding electrons from the carbon atom that the leaving group was
attached to (1). The electrons are pulled as the bond between the carbon atom and the leaving group
breaks. Some leaving groups are ... Show more content on Helpwriting.net ...
Safety is a priority. Always add acid to water, this reduces some of the heat created and does not
create any acid "spitting" in the hood. If sulfuric acid is spilled and comes in contact with skin, the
area should be washed with cold water and then with a dilute sodium bicarbonate solution. The
original solution once the 1–butanol, hydrobromic acid, and sulfuric acid were added was yellow–
orange in color. After distilling the distillate was clear then became partially cloudy. The calculated
yield of the product was approximately 5.41%. The calculated yield was low due to a fluctuating
temperature during the reaction and possible impurities formed. The presence of tertiary alcohols
creates an increase in the competitive elimination reaction when treated with phosphorus trihalides.
To produce a decent yield of tertiary alkyl halides the tertiary alcohols should be treated with
concentrated hydrogen halides (1). Creating 2–chloro–2–methylbutane from 2–methyl–2–butanol
and hydrochloric acid is an SN1 reaction that demonstrates the transformation. This mechanism can
be shown

Substitution Reaction Between 2-Butanol + H2
1.) A. The reaction between 2–butanol, anhydrous (CH3CH2CHOHCH3) and hydrogen bromine
(HBr) is a substitution reaction. Another example of a substitution reaction would be CH3Cl +
−OH→ CH3OH + Cl
b. The reaction between 4–methyl, pent–2–ene (CH3CHCHCH(CH3)2) and chlorine (CL2) is a
halogenations reaction or addition also known as chlorination. Another example of halogenation
reaction would be CH4 + Cl2 = CH3Cl + HCl.
c. The reaction in which 2–mthyl pentane is formed by 2–methyl 2–pentene is known as an addition
reaction. Another example of an addition reaction would be C2H4 (Ethene) + H2 = C2H6 (Ethane)
d. This reaction is esterification as ester CH3COOCH3 is formed along with water when acetic acid
is reacting with methanol. Also known as condensation reaction. Another example of esterification
would be C2H3CH2OH + CH3COOH = CH3COOCH2CH3 + H2O.
2.) ... Show more content on Helpwriting.net ...
This is a redox reaction.
b.) CH3COCH3and a reducing agent A ketone with a reducing agent will produce an alcohol. This is
a redox reaction.
3.) a.) Why is it possible for two products to form in this reaction?
It is possible for two products to form in the reaction because in the reactant is reacting with water
and water has an H and an OH group that could either attach to a single bonded carbon or a double
bonded carbon. In short, there are two possibilities as to where these molecules of water can

Alkyl Bromide Lab Report
Aim The purpose of this lab was to convert a primary alcohol to an alkyl bromide through SN2
reaction.
Introduction
A nucleophilic substitution reaction is when one group is substituted for another group and this
reaction proceeds via nucleophile. The SN2 reaction is one of the nucleophilic substitution reaction
where a nucleophile (electron rich) attacks a substrate that has a partial positive charge which expels
the leaving group out. The nucleophile attacks the carbon bonded to the leaving group from the
back, which leads to an inversion of stereochemistry. This reaction has only one step such that the
nucleophilic attack and the leaving group leaving happens in one concerted step. Some factors
which are essential for a SN2 reaction are that the carbon must be a methyl or primary carbon,
sometimes the reaction works with secondary carbons, but tertiary carbons are not reactive. This is
due to steric hindrance expressed by secondary and tertiary carbons. The nucleophile will not be
able to attack on ... Show more content on Helpwriting.net ...
The reactants were 1– butanol, H2SO4 and HBr. The limiting reagent in this reaction was 1–
butanol. The moles of 1– butanol that was used in this reaction were 5.00g/(74.1 g/mol)= 0.0674
moles. The percent theoretical yield should be 100% and since 1 mol of 1– butanol should result
also result in 1 mol of 1 bromobutane. The theoretical yield of the product should be 0.0674 moles.
The experimental mass of the product 1– bromobutane was 3.390 g and the molar mass of 1–
bromobutane is 137.0 g/mol. So, the moles of the product are 3.390g/(137.0g/mol)= 0.0247 moles.
Hence, the yield of this reaction is 0.0247/0.0674x 100= 36.65%. The yield was very low due to
errors such as inconsistent heat applied during refluxing and simple distillation, error while
transferring the product from the distillate to a flask and the product could have dissolved all leading
to low

Essay about Rxn of Iodoethane with Sodium Saccharin
Title: Reaction of Iodoethane with Sodium Saccharin– Ambient Nucleophile
Dates Performed: February 21 + 28, 2013
Date Submitted: March 14, 2013
Abstract:
The product ratio of N–ethylsaccharin to O–ethylsaccharin that occurred due to alkylation with
iodoethane at 80 oC was determined to be 81.5% to 18.5%, respectively, based on an analysis of the
1H NMR spectrum that was collected. The melting point range of 87.8–94.7 oC also indicated that
the mixture was largely composed of N–ethylsaccharin. The more prevalent product structure is:
C2H5I
C2H5I
And/Or
And/Or
N–ethylsaccharin product O–ethylsaccharin product
Experimental Procedure:
Sodium saccharin ... Show more content on Helpwriting.net ...
N– saccharin is more stable than O–saccharin, so it should be the major product of the reaction, if
not the only product, if the reaction reaches thermal equilibrium. A reaction involving the oxygen as
the nucleophile should occur faster than one involving nitrogen because the oxygen is more
electronegative. This electronegativity would attract the attack of the nucleophile more so than the
Nitrogen atom would. Based on the 1H NMR spectrum that was collected, a few things can be
determined. Based on deshielding and electronegativity, the peak that occurs around 4.7ppm is
associated with the O–ethylsaccharin product and the peak at 3.8 ppm is associated with the N–
ethylsaccharin product. Based on the height ration, the N–ethylsaccharin product is the more
prevalent result. The solvent that was chosen for the experiment is a polar aprotic solvent that can be
used to stabilize charge. This stabilization can also be used to stabilize an ionic transition state. This
stabilization of the transition state along with the nature of the products based on the chemical
properties would encourage the reaction to proceed toward the N–ethylsaccharin product. This
product is more stable

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

Strong Nucleophilic Substitution Report
Identifying Substitution Reactions of Strong Nucleophilic Compounds and Polar Protic Solvents
with Analytical and Experimental Instruments
Oshi Bonhomme, Courtney Lasher, Olivia Trusty*
Department of Chemistry and Chemical Biology, IUPUI, 402 N. Blackford St., Indianapolis, IN
46202 otrusty@indiana.edu The three reactions investigated through various experimental testing
contain an alcohol leaving group positioned on primary or secondary carbons. The substitution
method (SN1 or SN2) used in the reactions vary and are influenced by various factors. The position
of the alcohol and the number of steps are variables used to identify the substitution method. The
products formed are influenced by the substitution mechanism. The data reported shows ... Show
more content on Helpwriting.net ...
In order for SN1 and SN2 reactions to occur, the leaving group must be attached to an alkyne or
alkene (alkyl halides) 3. In nucleophilic substitution, there are two events that occur, development of
a new σ bond to the nucleophile and the σ bond to the leaving group breaks. The timing of these
events determines the type of mechanism2. The main difference between the two mechanisms is that
the SN2 reaction occurs in one step and the SN1 reaction occurs in two steps. The number of steps
in the reactions is influenced by many factors, including the rate law, nucleophile, and solvent. The
rate law (unimolecular or bimolecular) is the rate determining step. For a SN1 reaction has a weak
(neutral) nucleophile and is unimolecular, which means that the rate of the reaction is depending on
the concentration of the substrate. A SN2 reaction has a strong (negatively charged) nucleophile and
is bimolecular, where the rate of the reaction is dependent on the concentration of the substrate and
nucleophile 3. The strength of the nucleophile is important in identifying the type of reactions
because SN1 usually has weak nucleophiles and SN2 usually has strong nucleophiles. The type of
solvent used in the reaction is also an important factor in determining the number of steps because
SN1 reactions favor polar protic solvents (alcohols, carboxylic acids, and water). SN2 reactions tend
to proceed with polar aprotic solvents (DMSO and acetone) 3. Another factor involves the location
of the leaving group. SN2 reactions favor leaving groups in the primary location but can also work
for leaving groups in the secondary location. SN1 reactions favor leaving groups in the tertiary
location and can work for the secondary

Sn2 Nucleophilic Substitution Lab Report
1 and 2) In this experiment, Sn2 nucelophilic substitution between an unknown nucleophile solution
and the known reagents benzyl bromide and NaOH occurred to form a benzyl ether product. 3)
Refluxing, recrystallization, melting point, and TLC were used to purify and identify the products of
the reaction. 4) In order for nucleophilic substitution to take place, an electron pair donor (the
nucleophile) and an electron pair acceptor (the electrophile) with a good leaving group must be
present. In this experiment, Sn2 nucelophilic substitution occurred. In Sn2 nucelophilic substitution,
the nucleophile performs a "backside attack" at the same time the leaving group "leaves", resulting
in an inversion of configuration of the electrophile to form ... Show more content on Helpwriting.net
...
TLC in 9:1 hexanes/ethyl acetate solvent gave Rf Values for given solutions A–F and the filtrate as
.102, .061, .122, .347, .298, .404, .426, .064, and .280, respectively. 13) The product obtained was
4–tert–butylbenzylphenolether. The melting point range of the pure, unknown compound (35–44
°C) was closest to the one measured for 4–tert–butylbenzylphenolether (36–51 °C). Also, the scale–
like appearance of the unknown solid was very similar to the appearance of 4–tert–
butylbenzylphenolether. The NMR spectra solution #33 (the unknown) matched closest to that of 4–
tert–butylbenzylphenolether 14) The yield (.468 g) makes sense because it was lower than the
theoretical yield calculated (1.57 g). Yield may have been lost because the crystals formed too
quickly, causing some of them to be small in size and seep through the filter and into the filtrate. 15)
The percent recovery of 55.7% makes sense. The recovery is lower than 100% because the product
contained impurities before it was recrystallized, which made it heavier in mass. After
recrystallization, these impurities were removed, causing the final pure product to have less mass.
These impurities were confirmed to exist through

Nucleophilic Substitution Lab Report
A unimolecular nucleophilic substitution of t–amyl alcohol should be done to convert into t–amyl
chloride through extraction and simple distillation. A concentrated hydrochloric acid was added to
the reactant to force the reaction to take place. Infrared spectroscopy was utilized to verify that the
contents of the tert–amyl chloride should be different from the starting material.
In this reaction, a rate–determining step should occur through the ionization between carbon and –
OH bond to form an intermediate.11 This step should be followed by rapid reaction of a nucleophile
to wrap up the substitution.11 For this experiment, hydrochloric acid was used to drive off the
reaction, which contains a chlorine ion, a common nucleophile. (1)Chlorine ion is more effective as
a nucleophile than water; because an ion holds a negative charge and resulting in a faster rate of
reaction, whereas water holds a neutral charge, resulting in a slower rate of reaction with a
carbocation intermediate.13 The starting ... Show more content on Helpwriting.net ...
One supporting evidence is that the resulting infrared spectra in Figure 2 for the product still
contains an OH stretch of 3343 cm–1. In fact, the stretch of OH in the product is broader than the
stretch of the starting material in Figure 1. This could imply that the layers in the separatory funnel
initially did not form, although a lot of time has taken to settle. Adding 10% sodium chloride to the
mixture helped to form layers, but that does not necessarily mean that the –OH group had
completely separated from the carbocation. And so, the resulting product is not pure. Furthermore, it
is expected that the C–Cl stretch (between 850 to 550 cm–1) and C–H wag (1300–1150 cm–1)
should appear on Figure 2, but that did not happen. Moreover, the reaction failed since the amount
of tert–amyl alcohol used was not a lot enough to form an expected

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
Helpwriting.net ...
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

Substitution Reactions, Purification, and Identification Introduction (Q:1&2) An unknown
(nucleophile) was subjected to SN2 reaction when combined with benzyl bromide (electrophile) in a
sodium hydroxide (base) solution. The experiment provided a clear understanding in conducting
nucleophilic substitution reaction where heat must be applied in order for the SN2 reaction to move
forward. The goal was to determine the unknown by incorporating knowledge of polarity, the laws
of physics, and the role of energy when forming crystals; "like dissolves like", "matter cannot be
created nor destroyed". (Q3:Techniques) Melting point, recrystallization, and thin layer
chromatography (TLC) mediated the ability to find which unknown nucleophile was provided ...
This was concluded by combining information on melting points and TLC; melting range narrowed
when filtered product was mixed with the standard product. Also, the Rf value of the pure product is
closely related to the Rf value of the standard. TLC of filtrate showed no movement of the substance
in the mixture under 9:1 ratio declaring the substance to be extremely polar. Of the three potential
unknown reactants, 4–methoxyphenol would be the most polar and therefore would travel least up
the TLC plate. (Q14:Yield) 81.2% product yield was collected. "Matter cannot be created nor
destroyed", therefore some product could have filtered through. TLC of filtrate confirmed remnants
of product present. Filtering the filtrate could have increased the yield. (Q15:Recovery) The percent
recovery of the product makes sense because it is the mass of the crystallized product divided by the
crude product: 94.9%. The percentage reflects the mass of pure product (without the presence of
impurities). (Q16:MP) Melting point coincides with the unknown nucleophile being 4–
methoxyphenol because when the standard product was combined with our pure product, the
melting range narrowed. When compared to the melting ranges obtained when mixed with the other
two possible products the melting ranges significantly decreased and widened. This is often an
indication of impurities being present, but because this was a

The Substitution Mechanisms ( Sn1 And Sn2 ) With Reactions
This paper was written in order to relate nucleophilic substitution mechanisms (SN1 and SN2) with
reactions that involved converting alcohol–containing compounds to alkyl halides. This experiment
was conducted by combining the initial alcohol with reagents and heating under reflux when
necessary. It was determined that mechanistic pathways of substitution depend principally on the
structure of the initial alcohol; that is, substrate is considered primary, secondary, or tertiary.
Synthesis of 1 (46%) was achieved through SN2 mechanism from a primary alcohol, while
syntheses 2 (97%) and 3 (98%) were completed by SN1 mechanisms from secondary and tertiary
alcohols as determined by the presence of rearranged products. Many mechanistic reactions are
utilized and are interrelated in order to produce the desired product in an organic synthesis. These
mechanisms may be generally categorized2 into the following classes: addition, elimination,
substitution, and rearrangement. Of these, substitution reactions are of particular significance in
halogenation reactions of alcohol–containing compounds, in which the alcohol functional group is
replaced by a halide ion (i.e. Cl– or Br–). Alcohols are the most common precursors to alkyl halides
and signify a very substantial reaction in organic synthesis4. Substitution reactions can occur via
two mechanisms2, namely unimolecular nucleophilic substitution (SN1, a stepwise process) and
bimolecular nucleophilic substitution (SN2, a

Relativities of Alkyl Halides in Nucleophilic Substitution...
Title: Relativities of Alkyl Halides in Nucleophilic Substitution Reactions
Introduction:
The purpose of this lab was to perform a comparison of relative reactivities of various alkyl halides
with two different reagents, sodium iodine in acetone and silver nitrate in ethanol. (Below are the
reaction equations). We used different substrates, which were primary, secondary, and tertiary. These
substrates included 2–bromobutane, 2–bromo–2–methylpropane, 1–bromobutane ∞–Bromotoluene,
bromobenzene, and I–bromoadamantane. This lab helped discover what kind of mechanisms (either
SN1 or SN2) are involved in the performed reactions. 1. Sodium Iodine in Acetone:
RX + NaI –––––Acetone––––> RI + NaX (X=Br) 2. Silver Nitrate in ... Show more content on
Helpwriting.net ...
| Bromocyclohexane | 2° | RT: NO changeAfter heating: Evaporated slightly, made crystals, light
yellow | Slower SN1 reaction due to secondary carbon. | 1–bromoadamantane | 3° | RT: No
changeAfter Heating: Evaporated slightly, clear crystals formed | SN2 |
Sliver nitrate in ethanol reactions: Alkyl Halides | Classification of RX | Observations | Conclusion |
2–bromobutane | 2° | RT: Precipitate and densely cloudy.No heating required | Slower SN1 reaction
due to secondary carbon. | 2–bromo–2–methylpropane | 3° | RT: ClearAfter heating: No change |
Fast SN1 reaction due to it being a tertiary carbon. | 1–bromobutane | 1° | RT: Precipitate and
slightly cloudy.NO heating required | Heating required due to primary carbon SN2 reaction | ∞–
Bromotoluene | 1°Benzylic | RT: Precipitate and very cloudy.No heating required | Heating required
due to primary carbon SN2 reaction | Bromobenzene | 1°Allylic Vinylic | RT: ClearAfter heating: No
change | Heating required due to primary carbon SN2 reaction | 1–bromoadanabtane | 3° | RT:
Precipitate and cloudyNo heating required | Fast SN1 reaction due to it being a tertiary carbon. |
Conclusion:
In conclusion, out of the reactions for NaI in acetone, 1–bromobutane reacted the fastest, and did not
require

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

Essay about Lab Report
Synthesis of Butyl Benzoate Using Phase Transfer Catalysis
The objective of the experiment is to synthesize the butly benzoate by nucleophilic substitution and
characterize it by IR spectroscopy. The percent yield of the final product is determined after the
synthesis.
Procedures:
2.0 mL of 1–bromobutane, 3.0 g of sodium benzoate, 5.0 mL of water, 4 drops of
Aliquat 336, and a boiling stone were placed in a 50mL round–bottomed flask. The reaction mixture
was refluxed for 1 hour and the flask was cooled in a beaker in the water of room temperature. The
solid was formed in the mixture and the flask was shaken until it dissolved. The flash was rinsed
with 15 mL dichloromethane and it was added to the separating funnel. 10 mL of ... Show more
content on Helpwriting.net ...
fig)
Discussion
1) Errors & discrepancy
Firstly, the error of the percent yield or 18.8% yield of final product was due to the transfer of
reactions of organic layers to the Erlenmeyer flask several times, which led to the lost of the final
products. Besides, the excess benzoate was not entirely removed by the water and remained in the
final product. For the step of adding NaCl, the water was not entirely extracted from the organic
product as only several times of the extraction were done in the experiment.
2) Mechanism of the reaction
The above is the mechanism of the nucleophilic substitution (SN2), which the negative
O atom attacks the positive C atom and form the intermediate product in the second step. Br is
replaced by the benzoate ion and Br– is formed at the end of the reaction.
Conclusion
Butyl benzoate is synthesized through the nucleophilic substitution and the percent yield of the final
product is 18.8% from the experiment.
1) How is the phase transfer catalyst removed from product?
Water and dichloromethane are used to dissolve the phase transfer catalyst to the aqueous stage.
Then, the aqueous layer with the catalyst can be removed by using the separating funnel. Besides,
dehydrating agent can also be used to further remove the catalyst in the aqueous layer.

2) What purpose does washing with 15% (half–saturated) NaCl solution serve?
The 15% NaCl solution is to extract the water from the organic

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
Helpwriting.net ...
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

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,

Iodination Of Salicylamide Lab Report

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