UNIVERSITI TEKNOLOGI MARA PAHANG

CHM258: FUNDAMENTAL OF ORGANIC CHEMISTRY

LABORATORY REPORT

NO. EXPERIMENT : 1

TITLE : REACTIONS OF HYDROCARBONS AND ALKYL HALIDES

GROUP : AS1203H

GROUP MEMBERS :

NO. NAME STUDENT ID

1. Aida Nasreen binti Adnan 2019409728

2. Nur Husna Najwa binti Zulkifli 2019236366

3. Nur Erin Adrina binti Suhaimi 2019237204

4. Nur Izzah Hanum binti Mohd Nizan 2019440444

5. Nur Fatihah binti Mohamad Jamhuri 2019203636

DATE OF SUBMISSION : 8 JANUARY 2021

LECTURER’S NAME : DR. AGUSTONO WIBOWO

EXPERIMENT 1: REACTIONS OF HYDROCARBONS AND ALKYL HALIDES

OBJECTIVES:

1. To investigate the solubility of hydrocarbon compounds.

2. To compare the chemical reactivity of aliphatic hydrocarbon and aromatic
hydrocarbon compounds.
3. To assess the reactivity of alkyl halide compounds.

INTRODUCTION:

Hydrocarbons are organic compounds composed entirely of carbon and hydrogen

atoms. They are obtained primarily from natural sources such as coal, petroleum, and
natural gas. The major uses of hydrocarbons are as fuels and solvents. Hydrocarbons differ
primarily in the functional group (alkane, alkene, alkyne, aromatic). They may be saturated
or unsaturated. A saturated hydrocarbon contains only single C-C bonds (sigma (σ) bond).
An unsaturated compound contains at least two carbon atoms with sigma (σ) and pi (π)
bonds. Aromatic hydrocarbons are cyclic compounds whose structure is related to that of
benzene, with six - electrons in a six-member ring. In general, π-bond is much weaker than
σ-bond. In many cases the π-bond will involve a chemical reaction and the σ-bond will
remain unaffected. The common chemical tests for unsaturation hydrocarbon in laboratory
are using bromine, potassium permanganate and sulfuric acid. Thus, the following
experiments illustrate some of the fundamental reactions of saturated, unsaturated and
aromatic hydrocarbons.

Alkyl halide is a compound that contains at least one halogen group attached to an
alkyl group. Fluoride, chloride, bromide and iodide are examples of halogen groups. Iodide
ion is an excellent nucleophile and is soluble in acetone. These properties along with the
non-polar nature of acetone favor the SN2 reaction. The reaction can be followed since
sodium chloride and sodium bromide are not soluble in acetone and will precipitate from
solution. When an alkyl halide is treated with an ethanolic solution of silver nitrate, the silver
ion coordinates with an electron pair on the halogen, weakening the carbon-halogen bond
and resulting in the formation of an insoluble silver halide. This reaction proceeds via an S N1
mechanism. The nitrate ion is a very poor nucleophile and ethanol favors ionization of the
halide. As a result, alkyl nitrates do not form by an SN2 reaction.

APPARATUS:
 1. Small test tubes
2. Test tube rack
3. Test-tube holders
4. Stopper
5. Bunsen burner
6. spatula

CHEMICALS:

1. Bromine water
2. Potassium permanganate
3. Heptane
4. Cyclohexane
5. Cyclohexene
6. Hexyne
7. Toluene
8. 1-bromobutane
9. 2-bromobutane
10. 2-bromo-2-methylpropane
11. Sodium iodide in acetone
12. Ethanolic silver nitrate

PROCEDURE:
PART A: PHYSICAL PROPERTIES OF HYDROCARBON COMPOUNDS

I. Test for water solubility

1. 1 mL of hydrocarbons ( cyclohexane, cyclohexene, hexyne, and toluene )
was placed into four different test tubes.
2. 1 mL of water was added into each test tube.
3. The test tube was swirled gently to mix the solution.
4. The test tube was allowed to sit undisturbed for a minute.
5. The observation was recorded in term of solubility ( miscible or immiscible )

II. Test for solubility in heptane

1. 1 mL of hydrocarbons (cyclohexane, cyclohexene, hexyne, and toluene ) was
placed into four different test tubes.
2. 1 mL of heptane was added into each test tube.
3. The test tube was swirled gently to mix the solution.
4. The test tube was allowed to sit undisturbed for a minute.
5. The observation was recorded in terms of solubility (miscible or immiscible ).

PART B: CHEMICAL PROPERTIES OF HYDROCARBON COMPOUNDS

I. Combustion of Hydrocarbons
1. The Bunsen burner was ignited and the flame was observed.
2. 2 drops of each hydrocarbon (cyclohexane, cyclohexene, hexyne and
toluene) was placed on different spatulas.
3. The hydrocarbon was ignited carefully using a bunsen burner and was
removed immediately from the burner.
4. The observation was recorded based on the characteristics (color and
amount of smoke) of each flame along with any residue left behind on the
spatula (formation of soot ).

II. Reaction with Bromine

 A. Aliphatic hydrocarbon
1. 1 mL of each hydrocarbon compound ( cyclohexane, cyclohexene, and
hexyne ) was placed into three different test tubes.
2. 4 drops of bromine water solution was added to each test tube.
3. The test tube was swirled gently to mix the solution.
4. The test tube was allowed to sit undisturbed for 2 minutes.
5. The observation obtained was recorded.

B. Aromatic hydrocarbon

1. 1 mL of toluene was placed into a test tube.

2. A few iron fillings were added to one test tube.
3. 4 drops of bromine water was added into each test tube.
4. The test tubes were placed in a warm water bath for 15 minutes.
5. The observation obtained was recorded.

III. Reaction with Potassium Permanganate (Baeyer’s test)

A. Aliphatic hydrocarbon
1. 1 mL of hydrocarbon compounds (cyclohexane,cyclohexene and hexyne )
was placed into three different test tubes.
2. 2 mL of potassium permanganate solution was added into each test tube.
3. The test tube was shaken well and let it stand for 2 minutes.
4. The observation was recorded.

PART C: REACTION OF ALKYL HALIDE

Precaution steps :

1. Each test tube was performed in a clean test tube. The test tube was rinsed with
-0.25 mL ethanol and acetone after rinsed with water.
2. Reagents were not contaminated with samples or other reagents.
3. The results was examined to make sure that they make sense(for example: a 3͐° alkyl
halide should not react via an SN2 mechanism faster than a 1° alkyl halide).
4. The chemical tests were repeated for confirmation.

I. Effect of structure alkyl halides on the rates of SN2 and SN1 reactions.
A. SN2 reaction
1. 2 drops of each alkyl halide (1-bromobutane, 2-bromobutane and 2-bromo-2-
methylpropane) into three clean test tubes.
2. 2 mL of sodium iodide in acetone was added into each test tube and the
content was mixed thoroughly and the time was noted.
3. The test tube was placed in a water bath (-50° ) with no reaction within 5
minutes.
4. The observation and the time of the first appearance of any cloudiness or
precipitate was recorded.

B. SN1 reaction

1. 2 drops of each alkyl halide (1-bromobutane, 2-bromobutane and

2-bromo-2-methylpropane) was placed into three clean test tubes.
2. 2 mL of ethanolic silver nitrate was added into each test tube and the content
was mixed thoroughly and the time was noted.
3. The test tube was placed in a water bath (-50° ) with no reaction within 10
minutes.
4. The observation and the time of the first appearance of any cloudiness or
precipitate formed was recorded.

II. Effect of solvent polarity on SN1 reactions

 1. 0.5 mLof 2-bromo-2-methylpropane was placed into two clean test tubes.
2. Into each test tube was added:

I. test tube 1 (T1): 2 mL of ethanolic silver nitrate

II. Test tube 2 ( T2): 2 mL of (50:50)ethanolic silver nitrate: water

3. The content was mixed thoroughly and the time was noted.
4. The observations and the time of the first appearance of any cloudiness or precipitate
formed was recorded.

III. Effect of the concentration on the rate of SN2 reactions.

1. Four clean test tubes were prepared.

2. Into each clean test tube was added:
● Test tube 3 (T3): 0.5 mL of 1-bromobutane + 2 mL of sodium iodide in
acetone.
● Test tube 4 (T4): 0.5 mL of 1-bromobutane + 2 mL of (50:50) acetone:sodium
iodide in acetone solution.
● Test tube 5 (T5): 1.0 mL of 1-bromobutane + 2 mL of sodium iodide in
acetone.
● Test tube 6 (T6): 1.0 mL of 1-bromobutane + 2 mL of (50:50) acetone: sodium
iodide in acetone solution.
3. The content was mixed thoroughly and the time was noted.
4. The observations and the time of the first appearance of any cloudiness or precipitate
formed was recorded.

RESULTS:
PART A: PHYSICAL PROPERTIES OF HYDROCARBON COMPOUNDS

I. Test for water solubility

Compound Observation Miscible / Immiscible

Cyclohexane There is formation of layers inside the test

Immiscible
tube

Cyclohexene There is formation of layers inside the test

Immiscible
tube

Hexyne There is formation of layers inside the test

Immiscible
tube

Toluene There is formation of layers inside the test

Immiscible
tube

II. Test for solubility in heptane

Compound Observation Miscible / Immiscible

Cyclohexane There is no formation of layers inside the

Miscible
test tube

Cyclohexene There is no formation of layers inside the

Miscible
test tube

Hexyne There is no formation of layers inside the

Miscible
test tube

Toluene There is no formation of layers inside the

Miscible
test tube

PART B: CHEMICAL PROPERTIES OF HYDROCARBON COMPOUNDS

I. Combustion of Hydrocarbons

Compound Observation Chemical Equation

Cyclohexane Yellow and non-sooty flame C6H12 + 9 O2 ͢ 6 CO2 + 6 H2O
Cyclohexene Yellow and sooty flame 2 C6H10 + 17 O2 ͢ 12 CO2 + 10 H2O
Hexyne Yellow and sooty flame C6H10 + 17/20 O2 ͢ 6 CO2 + 5 H2O
Toluene Yellow, sooty flame and carbon residue C7H8 +9 O2 ͢ 7 CO2 + 8 H2O

II. Reaction with Bromine

Compound Observation Chemical Equation

Cyclohexane The solution turns orange yellowish C6H12 + Br2 ͢ No reaction
Cyclohexene The solution turns colourless C6H10 + Br2 ͢ C6H10Br2
Hexyne The solution turns cloudy C6H10 + Br2 ͢ C6H10Br2
Toluene [with iron Brown precipitate is formed C7H8 + Br2 + Fe ͢ C7H7Br + HBr
filling]
Toluene [without The solution turns orange yellowish C7H8 + Br2 ͢ No reaction
iron filling]

III. Reaction with Potassium Permanganate (Baeyer’s test)

Hydrocarbon Observation Chemical Equation

Cyclohexane No reaction occurs C6H12 + KMnO4 ͢ No reaction
Cyclohexene Brown precipitate formed C6H10 + KMnO4 ͢ C6H12O2

Hexyne Red precipitate formed C6H10 + KMnO4 ͢ C6H12O2

Toluene No reaction occurs C7H8 + KMnO4 ͢ No reaction

PART C: REACTION OF ALKYL HALIDE

I. Effect of structure of alkyl halides on the rates of SN2 and SN1 reactions

Reagent Alkyl Halide

1-bromobutane 2-bromobutane 2-bromo-2-methylpropane

SN2 (Sodium The solution turns The solution turns The solution turns cloudy at
iodide in acetone) cloudy at a very fast cloudy at a a very slow rate
 rate moderate rate

SN1 (Ethanolic The solution turns The solution turn The solution turns cloudy
silver nitrate) cloudy at a very slow cloudy and white and white precipitate is
rate precipitate is formed formed at a very fast rate
at a moderate rate

II. Effect of solvent polarity on SN1 reaction

Test tube Observation (Precipitate/ Time taken)

T1 The solution turns cloudy and white precipitate is formed at a fast rate

T2 The solution turns cloudy and white precipitate is formed at a fast rate

III. Effect of concentration on the rate of SN2 reactions

Test tube Observation (Precipitate/ Time taken)

T3 The solution turns cloudy and white precipitate is formed at a fast rate

T4 The solution turns cloudy and white precipitate is formed at a slow rate

T5 The solution turns cloudy and white precipitate is formed at a very fast rate

T6 The solution turns cloudy and precipitate is formed at a fast rate

DISCUSSION:

PART A: PHYSICAL PROPERTIES OF HYDROCARBON COMPOUNDS

The experiment showed solubility in water for four types of hydrocarbons. Water is a
polar solvent which results in all hydrocarbons used in this experiment not mixing well with
each other. All hydrocarbons are nonpolar which means all hydrocarbons will be insoluble in
water. There is slightly solubility in water among the hydrocarbons but it is very poor. Most
density of hydrocarbons is less than water which results in two layers forming inside the test
tubes. They are floating on top of the water. When water mixed with a non-polar substance
which are hydrocarbons, there are no forces attracted between them making them separate
from each other. This is because hydrocarbons do not contain electronegative atoms
because of little or no polarity in them. Non-polar substances can attract each other but not
strongly and are not attracted to polar substances which is why cyclohexane, cyclohexene,
hexyne and toluene cannot mix together as shown in the experiment.

Heptane can be classified as ligroin and an organic solvent. For heptane solubility
test, all used hydrocarbons are miscible in heptane. Heptane can be a non-polar solvent
which is why it can be mixed together with cyclohexane, cyclohexene, hexyne and toluene.
Hydrocarbons are most likely to dissolve in an organic solvent that is why there is no
formation of layers in the test tubes. Heptane is a non-polar substance and hydrocarbons
also are non-polar substances so there are many electrostatic interactions between the two
nonpolar molecules. However, the interaction between the two nonpolar substances is not
as strong as dipole-dipole interaction which is the positive part of the polar molecule
attracted to the negative part of a polar molecule. Non-polar molecules attracted to each
other are called induced dipole-induced dipole interactions. This interaction can be explained
when the negative part of which the electrons of one of the molecules was attracted to the
positive part which is the nucleus of another molecule. This resulted in the induced-dipole
interactions between heptane and cyclohexane, cyclohexene, hexyne and toluene.

In part A experiment, error in this experiment can be avoided by swirling the

substances together properly. Error also can be avoided by measuring the substances
following the procedure given.

PART B: CHEMICAL PROPERTIES OF HYDROCARBON COMPOUNDS

When analysing and comparing the chemical properties of the hydrocarbons which
are cyclohexane, cyclohexene, hexyne and toluene, the results obtained were found to differ
among them.

The major component in natural gas is the hydrocarbon methane. Another example
of hydrocarbons used for heating or cooking purposes are propane and butane. The
combustion tests had different results for each hydrocarbon with cyclohexane having clear
flame and leaving no residue left out of all hydrocarbons. Whereas cyclohexene, hexyne and
toluene had dark smokes, toluene left carbon residue. Aromatic hydrocarbons such as
toluene contain greater carbon to hydrogen ratio. The products formed in the combustion
process are carbon dioxide and water with heat being evolved as well.

Based on experiments conducted to observe the reaction of hydrocarbons with

bromine water, unsaturated hydrocarbons react rapidly with bromine in a solution of
cyclohexane. The reaction is the addition of the element bromine to carbons of the multiple
bonds. Alkenes and aromatic hydrocarbons will react with bromine in the solution in order to
produce the corresponding alkyl bromide or dibromoalkane. The orange yellowish colour of
bromine will disappear when it reacts with alkenes because the bromoalkane products are
usually colourless. Alkanes only have single carbon bonds (C-C) present, no visible reaction
with bromine water is observed. The orange yellowish colour of the bromine water would
remain. On the other hand, aromatic compounds resist additional reactions due to the
possession of a closed loop of electrons, so when bromine reacted to toluene in a presence
of iron filings, it was possible to notice a darker colour precipitate because alkanes undergo
substitution reaction. Saturated hydrocarbons are unreactive because alkynes react slowly
and require a catalyst.

Potassium permanganate is an oxidising agent that reacts with unsaturated aliphatic

hydrocarbons, but does not react with alkanes or aromatic hydrocarbons. The reaction of
potassium permanganate with cyclohexane had no visible reaction because alkanes are
unreactive near oxidising agents due to the strong and stable bonds. However, when
potassium permanganate was added to cyclohexene, there was a colour change because of
the characteristic of alkenes as they voluntarily oxidise and produced MnO2, a brown
precipitate.

PART C: REACTION OF ALKYL HALIDE

The experiment was conducted to access the reactivity of alkyl halide compounds.
The high reactivity of alkyl halides can be explained in the terms of C-X bond which is highly
polarized covalent bond due to large difference in the electronegativities of carbon and
halogens atoms. The experiment is divided into three parts, the first part is to identify the
effect of structure alkyl halides on the rates of S N2 and SN1 reaction. For SN2, the alkyl halide
used was 2 drops of 1-bromobutane, 2-bromobutane and 2-bromo-2methylpropane were
placed into 3 different clean test tubes. The three test tubes were filled with 2mL of sodium
iodide in acetone and were stirred while the time was also recorded. For S N1, 2 drops of 1-
bromobutane, 2-bromobutane and 2-bromo-2-methylpropane were placed into 3 different
clean test tubes. The three test tubes were filled with 2 mL of ethanolic silver nitrate were
stirred and the time was also recorded.

The second part is to identify the effect of solvent polarity on SN1 reactions. two
different test tubes were filled with 0.5 mL of 2-bromo-2methylpropane. For test tube 1, the
content was mixed with 2 mL of ethanolic silver nitrate while the test tube 2, the content was
mixed with 2 mL 0f (50:50) ethanolic silver nitrate: water. Both test tubes are stirred and time
is recorded.

For the third part is to identify the effect of the concentration on the rate of SN2
reactions. Four clean test tubes were used and labelled as T3, T4, T5 and T6. The content in
T3 was added with 0.5 mL of 1-bromobutane + 2 mL of solution iodide in acetone. In T4, 0.5
mL of 1-bromobutane + 2 mL of (50:50) acetone:sodium iodide in acetone solution was
added. Next, the content in T5 was added with 1.0 mL of 1-bromobutane + 2 mL of sodium
iodide in acetone and for T6, the content in T6 was added with 1.0 mL 0f -bromobutane + 2
mL of (50:50) acetone:sodium iodide in acetone solution.

For the SN1 reaction, there is a carbon intermediate. Solvent of higher polarity tends
to stabilize those carbocations. Therefore, SN1 reaction occurs more readily in polar
solvents. The bromine leaves the group by breaking away to generate the carbocation
(positively charged carbon compound). When the carbocation is formed, the CH3CH2OH
nucleophile quickly attacks the positively charged carbon. Based on the result, the 1-
bromobutane with ethanolic silver solution turns cloudy at very fast rate, the 2-bromobutane
with ethanolic silver nitrate solution turns cloudy at a moderate rate and the 2-bromo-
2methylpropane with ethanolic silver nitrate solution turns cloudy and white precipitate
formed at a very fast rate. Since the first step is slow, the formation of carbocation will
determine the overall rate of reaction. The more favorable the carbocation formation, the
faster the rate of the overall SN1 reaction. Referring to the solvent polarity, a high polar
solvent will stabilize a charged ion such as carbocation much better than a non-polar
solvent. This is due to the solvent itself having partial positive and partial negative regions
which are dipole moments that could interact favorably with charged carbocation.

In part I for SN2 reaction is fastest for small alkyl halides (methyl > primary >
secondary >> tertiary). Based on the result, smaller alkyl halides like 1-bromobutane have a
very fast rate, while bigger alkyl halides like 2-bromo-2-methylpropane have a very slow rate.
 In addition, for SN2 reaction, by increasing the concentration, either the nucleophile or
the substrate will increase the rate of reaction. In this reaction, one bond is broken down and
another bond is formed at the same time. The rate law equation is r (rate) is equal to
k[CH3Br][OH⁻]. The equation shows that the rate reaction is directly proportional to [OH]⁻
and [CH3Br]. When the concentration of any reactant is increased, the rate of reaction is
increased. When the concentration of OH⁻ is increase, then the rate of reaction will be
increase because there are more OH⁻ ions attacking the substrate. Next, by increasing the
concentration of CH3Br, the rate of reaction will be increased because there are more
CH3Br molecules available to be attacked.

In part III which is the effect of the concentration on the rate of SN2 reactions. The
concentration of T4 is half than T3. This can be proven when the T4 solution turns cloudy
and white precipitate is formed at a slow rate compared to T3 which is T3 solution turns
cloudy and white precipitate formed at a fast rate. Next, the concentration of T6 is half than
T5. This can be proven when the T6 solution turns cloudy and white precipitate is formed at
a fast rate compared to T5 which is T5 solution turns cloudy and white precipitate formed at
a very fast rate. Thus, the rate of SN2 reaction is first order in the substrate and first order in
the nucleophile. If the substrate concentration is half, the reaction rate will be half. Similarly,
if the substrate concentration of the nucleophile is half, the rate again half.

In order to avoid any error in the experiment, make sure that the test tube was
cleaned before using it during the experiment to prevent the reagents from being
contaminated with samples or other reagents. Next, repeat the chemical tests for
confirmation to achieve the best results.

QUESTIONS:

1. Write a general statement regarding solubility of hydrocarbons in polar solvent

and non-polar solvent.

Hydrocarbons are built up of carbon and oxygen which makes it a nonpolar

substance. This means hydrocarbons are insoluble in polar solvent and soluble in
non-polar solvent.
2. Hydrocarbon may undergo complete and incomplete combustion under
different conditions. Briefly explain.

A complete combustion of hydrocarbons needs the presence of oxygen. The

products of this reaction are water and carbon dioxide gas. The incomplete
combustion occurred when there is no excess of oxygen present during the
combustion. It causes undesirable products to form.

3. Write a complete chemical equation for reaction of cyclohexane with Br 2 under

uv.

4. Suggest a complete chemical equation for Baeyer’s test of cyclohexene.

5. Explain which compound (cyclohexane or cyclohexene) is more reactive when

reacted with potassium permanganate solution.

Cyclohexene is more reactive than cyclohexane when reacted with potassium

permanganate solution.This is because cyclohexene has a carbon-carbon double
bond while cyclohexane has a single bond that causes it to have no reaction.

6. Arrange the following in order of increasing rate of substitution by the S N2

mechanism.
 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane

2-bromo-2-methylpropane, 2-bromobutane, 1-bromobutane

7. Arrange the compounds in Question 1 in order of increasing rate of

substitution by the SN1 mechanism.

1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane

8. What would be the effect of carrying out the sodium iodide in acetone reaction
with the alkyl halides using an iodide solution half as concentrated?

If the iodide solution were half as concentrated, the S N2 reaction would occur at half
the rate it normally would. Therefore, only half as much precipitate would form. Since
SN2 reactions favor a high concentration of the nucleophile, so the reaction would be
slower.

9. Provide an equation, clearly showing the stereochemistry of the starting

material and the product, for the reaction of 2-bromobutane with sodium iodide
in acetone.
 10. Briefly explain which compound (1-bromobutane or 1-chlorobutane) will react
faster when it is added with sodium iodide in acetone.

1-bromobutane react faster than 1-chlorobutane when sodium iodide was added in
acetone.Br- is bigger than Cl- ,thus bromine is a weaker base compare to
chlorine.Therefore, it can better stabilize the negative charge,making it a better
leaving group.

CONCLUSION:

In conclusion, hydrocarbons are organic compounds that are insoluble in water but
soluble in organic solvent. This is because hydrocarbons are non-polar solvent but water is
polar solvent so that's why hydrocarbons are insoluble in water because hydrogen bonds
cannot be formed by hydrocarbons. Water forms hydrogen bonds, a very strong type of
intermolecular bonding that requires the movement of hydrogen ions between molecules. In
order for a compound to dissolve in water, hydrogen bonds must also be
formed.However,aliphatic hydrocarbons are organic compounds composed of carbon and
hydrogen atoms, arranged in straight chains, branched structures or non-aromatic ring
structures. Aliphatic hydrocarbons can be found in three types as alkanes, alkenes, and
alkynes.Hence, aromatic hydrocarbons are compounds composed of carbon and hydrogen
atoms in ring structures with delocalized pi electrons.Aliphatic hydrocarbons are more
reactive than aromatic hydrocarbons because the bonds between carbon and hydrogen
atoms are weak that make them easily broken. Meanwhile, the interaction between the
carbon atoms in an aromatic ring are stronger that are hardly being broken. Alkyl halide is a
compound that contains at least one halogen group attached to an alkyl group.The S N2
reaction is concerted.That is, the SN2 occurs in one step, and both the nucleophile and
substrate are involved in the rate determining step. Therefore,the rate is dependent on both
the concentration of substrate and that of the nucleophile.The reaction of S N2 is favoured by
polar aprotic solvents,solvents such as acetone, DMSO, acetonitrile or DMF which are polar
enough to dissolve the substrate and nucleophile but do not participate in hydrogen bonding
with nucleophile.The SN1 reaction proceeds stepwise. The leaving group first leaves,
whereupon a carbocation forms that is attacked by the nucleophile.The reaction of S N1 tends
to take place in polar protic solvents such as water, alcohols, and carboxylic acids, which
stabilise the resulting (charged) carbocation from the loss of the leaving group.These
also,tend to be nucleophiles for these reactions.

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