The hydrolysis of 2-bromo-2-methylpropane

2-bromo2-methylpropane will undergo hydrolysis under different conditions to investigate a

number of things including:
What is the order of reaction with respect to the reactants?
What is the rate equation?
Whats the activation energy for this reaction and how much does having a catalyst present alter it?
How does increasing temperature alter the rate of reaction?
How will using a common ion affect the rate of reaction?

The Equation for the hydrolysis of 2-bromo-2-methylpropane is

C4H9Br + OH- C4H9OH + BrThe halogenoalkane will react with OH- ions - in a Propanone solution to produce Bromide
ions and an alcohol.

Hydrolysis of a haloalkane is a substitution reaction that occurs when it reacts with

hydroxide ion to eliminate the halogen to form an alcohol and a negatively charged halogen.
This type of hydrolysis is made possible as a result of the polar C-Br bond. The election deficient carbon is prone to attack by an electron-rich species which allows for nucleophilic
substitution to take place in which the OH- acts as a nucleophile and is attracted to the
carbon center. As the OH- ion approaches the electron-deprived carbon the bromide ion
begins to move away taking a pair of electron with it. This forms a transition state [3], where
both the OH and Br are bonded to the same carbon.

Equation 1 - Showing Hydrolysis of 2-Bromo-2-Methylpropane [2]

Tertiary hydrolysis-like the one occurring in this reaction- is an example of an SN1 reaction
which is made possible as tertiary carbocations are relatively stable in comparison to
secondary and primary ones. [1]
SN 1

This is an SN1 mechanism [research reference] as its unimolecular (only one molecule is
involved in the rate determining step), overall it involves two steps, the first being the slow
rate determining step in which the polar bond is broken, the second step involves the
attraction of two oppositely charged molecules being attracted to each other which requires
no significant energy which results in the reaction being fast in comparison to the first step.

SN 2

In contrast theres only one step involved in this reaction in which the bond breaking and
making happens simultaneously, this mechanism is SN2 as theres two molecules involved in the
rate determining step. This is seen in primary haloalkane hydrolysis as its carbocation is
unstable. In this mechanism a transition state is formed in which the central carbon is
partially bonded to both the Halide ion and the OH ion. Both these mechanisms both result
in the same outcome the rate equations for the two mechanisms are different.

Rate is a measure of how fast reactions take place and its affected by many conditions.
The Collision Theory states a bimolecular reaction will only occur when two particles collide
with enough energy to break existing bonds and form new ones, otherwise known as
overcoming the activation enthalpy.
In order for the reaction to take place the two particles must collide
whilst orientated correctly otherwise the reaction is not possibleThis is a result of all molecules having a specific shape [4] - if the two
active areas fail to match up during a collision the two molecules
will simply bounce off each other as shown.
The Maxwell Boltzmann Distribution Curve shows that only a small proportion of collisions
result in a reaction taking place. All molecules of
a particular chemical have the same mass
meaning the only thing affecting whether or not
a reaction will take place is their speed as
Kinetic Energy = mv2. The graph on the right
shows that there are a small percentage of
molecules at a given temperature with enough
Table 1 - Only particles in the shaded area have enough
energy to react. This curve explains why water
energy to react
will slowly evaporate at temperatures lower than
its boiling point. There are many factors that we
can change to help a higher percentage of molecules to overcome the activation enthalpy
including temperature, concentration and the addition of a catalyst.
Activation Enthalpy is the minimum amount of kinetic energy required by colliding
molecules for a reaction to take place (denoted by EA). There is a minimum amount as the
particles must collide with enough energy to stretch and break existing bonds and to form
new ones. Certain measures can be put in place to result in more particles reaching the
activation enthalpy.

Temperature affects the kinetic energy within molecules and can cause reactions to occur
at a faster/lower rate depending on how high/low it is, raising
the temperature by 10oC roughly doubles the rate of reaction.
By increasing temperature were increasing the chance of a
collision occurring and as a results collisions will occur more
often, as well as that collisions will be more violent and as a
result theres a greater chance in a collision resulting in a
reaction as its more likely the activation energy will be
reached. The graph summarises the effect of temperature,
increasing the temperature shifts the Maxwell Boltzmann distribution curve to the right as a
higher percentage of particles have enough kinetic energy to overcome the activation
enthalpy.
A Catalyst will speed up the rate of a reaction by providing an alternate pathway - with
lower activation energy- for the reaction to take
place. In the case of this Hydrolysis reaction a
common ion will be used to speed up the rate of
reaction.

Concentration has an effect on the rate of a reaction as by increasing the concentration of a

reacting substance you can increase the rate of a reaction as there are more particles
available to collide which will result in
more collision happening. With more
Collisions occurring, its more likely that a
reaction will occur. Concentration
however, will not always have an effect
on the rate of reaction as in the case of
this hydrolysis, if all carbons are already undergoing substitution, by increasing the amount
OH- ions in the solution, the reaction wont speed up as
shown in the graph.
In the case of gases, increasing the Pressure is equivalent to
increasing the concentration.

The Rate Equation will tell me the order of reaction with respect to each reactant and
catalyst if used. In order to find it Ill need to carry of a series of experiments using different
concentration of each reactant eventually resulting in a similar rate equation to the one
below.

Arrhenius Equation
A typical rate equation for A + B -> C

In order to find the order of reaction for each reaction Ill monitor the PH of the solution. By
adding 2 drops of Phenolphthalein at the beginning of the reaction, the NaOH will turn it
pink. Once the experiment begins I can use a colorimeter to help me monitor the progress
of the reaction. The Phenolphthalein will go colourless once the reaction has completed
allowing me to monitor the time it took at different concentrations of the reactant being
tested.
Using a range of concentrations of each reactant will help me figure out the order of the
reaction for each reactant which will in turn help put together a rate equation.
Colorimetry is an experimental technique that can be used to measure how much light a
substance absorbs. This technique can be used to calculate the concentrations of solutions.
By shining a light at a substance through an appropriate filter you can then use the
displayed values to create a calibration curve which will be directly proportional to the
concentration of the solution.
It can also be used to monitor the progress of a solution, By measuring the colour of a
solution you can use a colorimeter to see how long it takes for a reaction to reach an end
point provided the end point is dependant on colour change.
In the case of this hydrolysis Ill use a colorimeter to see how long it takes for my pink
solution to go colourless-removing human error.

Titration could have also been used to discover the rate of reaction however technique like
this one are less efficient.

Making of solutions

0.0.1dm3 NaOH
Experiment A = 6cm3 * 5 * 5 = 150cm3. | 150/395 * 1.975 = 0.75cm3
Experiment B = (2cm3*5) + (3cm3*5) + (4cm3*5) + (5cm3*5) + (6cm3*5) = 95cm3.
|95/395 *

1.975 = 0.475cm3

Experiment C = 6cm3 * 5 * 5 = 150cm3 | 150/395 * 1.975 = 0.75cm3

150cm3 + 95cm3 + 150cm3 = 395cm3
Concentration * Volume = Moles
0.01mol/dm3 * (395/1000) dm3 = 3.95x10 -3 moles
Moles

/ Concentration = Volume

(3.95x10 -3 M) / (2mol/dm3)

= 1.975x10-3 dm3 /1.975cm3

Pure 2-Bromo-2-Methypropane
Experiment A = 0.5cm3 * 5 * 5 = 12.5cm3
Experiment B = (0.9cm3*5) + (0.8cm3*5) + (0.7cm3*5) + (0.6cm3*5) + (0.5cm3*5) = 17.5cm3
Experiment C = 0.5cm3 * 5 * 5 = 12.5cm3
Experiment D = 0.5cm3 * 5 * 2 = 5cm3
5cm3 + 12.5cm3 + 17.5cm3 + 12.5cm3 = 47.5cm3
Propanone Solution
Experiment A = (3.0cm3*5) + (3.1cm3*5) + (3.2cm3*5) + (3.3cm3*5) + (3.4cm3*5) = 80cm3
Experiment B = (7.4cm3*5) + (6.4cm3*5) + (5.4cm3*5) + (4.4cm3*5) + (3.4cm3*5) = 135m3
Experiment C = 3.4 * 5 * 5 = 85cm3
Experiment D = 9.4cm3 * 5 * 2 = 470cm3
470cm3 + 85cm3 + 135cm3 + 80cm3 = 770cm3
Propanone = 770cm3 * 0.8 = 616cm3
Water = 770cm3 * 0.2 = 154cm3

Equipment List
Lab Coat
Safety Goggle
Colorimeter
Multiple test tubes
2 Burettes
Distilled water
620cm3 Propanone
1.975cm3 of 0.01mol/dm3 NaOH (freshly made)
5cm3 Phenolphthalein
50cm3 2-bromo-2-methylpropane (from a new bottle as old bottles hydrolyse over time on
standing)
1.0m3 calibrated pipette
Stop clock
Ice
Water Bath
White Tile

Plan

Experiment A consists of changing the concentration of C4H9Br whilst keeping everything

else consistent to determine the order of reaction with respect to C4H9Br.

Experiment B consists of changing the concentration of Sodium Hydroxide whilst keeping

everything else consistent to determine the order of reaction with respect to NaOH.
Experiment C consists of changing the temperature of the reaction whilst ensuring all other
variables remain constant.
Experiment D consists of adding a common ion to see the effect it has on the hydrolysis of
2-bromo-2-metylpropane

Experiment A

Table 2-Reagent table changing the concentration of 2-Bromo-2-methylpropane

Experiment
A1
A2
A3
A4
A5

C4H9Br/cm3 Propanone/
cm3
0.9
3.0
0.8
3.1
0.7
3.2
0.6
3.3
0.5
3.4

NaOH/mol3
cm (6cm3)
0.01
0.01
0.01
0.01
0.01

Temperature(.c)
Room Temp
Room Temp
Room Temp
Room Temp
Room Temp

1. Table 2 shows the volume and concentrations required for these set of
experiment.
2. Setup a burette containing Sodium hydroxide solution (0.01mol dm-3), ensuring
to run the alkali solution though the burette first.
3. Setup a burette containing propane solution remembering to run it through the
burette first.
4. In a volumetric pipette collect 0.1cm3 Phenolphthalein. In another volumetric
pipette, collect 0.9cm3 C4H9Br.
5. Run 6cm3 NaOH into a test tube and proceed to add 0.1cm3 Phenolphthalein
into the same test tube.
6. In a separate test tube add 3.0cm3 of solvent via burette and 0.9cm3 C4H9Br.
7. Prepare a stop clock to time the reaction. Double shuffle the test tubes to mix
and start the reaction. Whilst constantly stirring, record the temperature of the
solution.
8. Record the time taken for the solution to lose its colour.
9. Thoroughly rinse the test tubes before repeating the experiment with the same
values 5 times.
10. Repeat steps 2-8 for A2-5.

Experiment B

Experiment NaOH/
cm3
B1
2.0
B2
3.0
B3
4.0
B4
5.0
B5
6.0

C4H9Br/
cm3
0.5
0.5
0.5
0.5
0.5

Propanone
solvent/cm3
7.4
6.4
5.4
4.4
3.4

Phenolphthalein/
cm3
0.1
0.1
0.1
0.1
0.1

Temperature(.c)
Room Temp
Room Temp
Room Temp
Room Temp
Room Temp

Table 3- Reagent table changing the concentration of NaOH

1. Table 3 shows the

volume and concentrations required for these set of experiment.
2. Setup a burette containing NaOH (0.01mol dm-3), ensuring to run the alkaline
though the burette first.
3. Setup a burette containing propane solution remembering to run it through the
burette first.
4. In a volumetric pipette collect 1cm3 Phenolphthalein. In another volumetric
pipette, collect 0.5cm3 C4H9Br.
5. Run 0.5cm3 C4H9Br into a test tube and proceed to add 0.1cm3 Phenolphthalein
into the same test tube.
6. In a separate test tube add 3.6cm3 of solvent via burette and 5.8cm3 NaOH.
7. Prepare a stop clock to time the reaction. Double shuffle the test tubes to mix
and start the reaction. Whilst constantly stirring, record the temperature of the
solution.
8. Record the time taken for the solution to lose its colour.
9. Thoroughly rinse the test tubes before repeating the experiment with the same
values 5 times.
10. Repeat steps 2-8 for B2-5

Experiment C
Experiment Temperature(.c)
C1
C2
C3
C4
C5

10
15
20
25
30

Propanone/
cm3
3.4
3.4
3.4
3.4
3.4

C4H9Br/
cm3
0.5
0.5
0.5
0.5
0.5

NaOH/
cm3
6.0
6.0
6.0
6.0
6.0

1. Table 5 shows the volume and concentrations required for these set of experiment.
2. Place the Propanone Solvent in an ice bath.
3. Place 5cm3 C4H9Br in an ice bath to bring the temperature down to 5.c.Do the same
with 50cm3 NaOH.
4. Once the temperature of the solution has dropped setup a burette containing
Sodium hydroxide solution (0.01mol dm-3), ensuring to run the alkali solution though
the burette first. Repeat with the solvent
5. In a volumetric pipette collect 1cm3 Phenolphthalein. In another volumetric pipette,
collect 0.9cm3 C4H9Br.
6. Run 6cm3 NaOH into a test tube and proceed to add 0.1cm3 Phenolphthalein into the
same test tube.
7. In a separate test tube add 3.0cm3 of solvent via burette and 0.9cm3 C4H9Br.
8. Prepare a stop clock to time the reaction. Double shuffle the test tubes to mix and
start the reaction. Whilst constantly stirring, record the temperature of the solution.
9. Record the time taken for the solution to lose its colour.
10. Thoroughly rinse the test tubes before repeating the experiment with the same
values 5 times.
11. Repeat steps 2-8 for C2-5.

Experiment D

Experiment
D1

C5H9Br/c
m3
0.5

Propanone NaBr (s)

/cm3
9.4
0.43

LiCl (s)

Temperature(.c)

0.43

Room Temp

Table 7-Reagent table changing the length of the 2-Bromo-2-methylpropane chain

1. Table 7 shows the volume and concentrations required for these set of
experiment.
2. Create a solvent containing 3 parts propanone and 1 part water.
3. Dissolve 0.43g LiCl into 50cm3 of propanone
4. Setup this solution in a burette remembering to run it through the burette first.
5. In a volumetric pipette collect 1cm3 Phenolphthalein. In another volumetric
pipette, collect 0.9cm3 C5H9Br.
6. Run 0.5cm3 C5H9Br into a test tube and proceed to add 0.1cm3 Phenolphthalein
into the same test tube.
7. In a separate test tube add 9.4 of solvent via burette .
8. Prepare a stop clock to time the reaction. Double shuffle the test tubes to mix
and start the reaction. Whilst constantly stirring, record the temperature of the
solution.
9. Record the time taken for the solution to lose its colour.
10. Thoroughly rinse the test tubes before repeating the experiment with the same
values 5 times.
11. Repeat steps 2-8 using NaBr.

Health & Safety

The Laboratory must be kept ventilated.
Lab coats should be worn.
Eye protection should be worn.
Compound
2-Bromo-2-methylpropane.[7]

Concentration Hazard
Pure liquid

Causes Skin/Eye
Irritation in case of
contact.
Can cause irritation in
the digestive system.
May cause harm if
inhaled.
Highly flammable.

Max Conc =
8.015x10
mol/dm3

May Cause Skin/Eye

Irritation in case of
contact.

Risk Management
Rinse Skin/Eyes
thoroughly in case
of contact. Seek
Medical advice in
case of continued
irritation.
Avoid ingestion.
Seek Medical
Attention in case
of extended
Skin/Eye contact.
Keep away from
naked flames.
In case of large
spill-keep away
from heat/flames.
Dry with Sand and
stop leak without
risk.
Rinse hands/eye
Thoroughly.
Avoid extended
contact.

Propanone

Pure solvent

Highly Flammablekeep away from naked

flames/heat.
May cause irritation.
Keep away from open
wounds.
Causes Skin/Eye
Irritation in case of
contact.

Phenolphthalein[8]

NaOH

Pure

Highly Flammablekeep away from naked

flames/heat.

Max conc:
4.02x10cm-6

No real risk

2mol/dm3

Irritating to skin &

eyes in high
concentrations.

0.01 moldm-3

Can cause irritation in

the digestive system.
Avoid ingestion.

In case of large
spill-keep away
from heat/flames.
Dry with Sand and
stop leak without
risk.
Rinse Skin/Eyes
thoroughly in case
of contact. Seek
Medical advice in
case of continued
irritation.
Seek Medical
Attention in case
of extended
Skin/Eye contact.
In case of large
spill-keep away
from heat/flames.
Dry with Sand and
stop leak without
risk.
Treat as usual
chemical.
Rinse Skin/Eyes
thoroughly in case
of contact. Seek
Medical advice in
case of continued
irritation.
Seek Medical
Attention in case
of extended
Skin/Eye contact.

LiCl

Solid

Harmful is swallowed.
Irritating to skin &
eyes.

Rinse Skin/Eyes
thoroughly in case
of contact. Seek
Medical advice in
case of continued
irritation.
Seek Medical
Attention in case
of extended
Skin/Eye contact.

0.01 moldm-3
NaBr

Solid

0.01 moldm-3

Harmful is swallowed.
Irritating to skin &
eyes.

Rinse Skin/Eyes
thoroughly in case
of contact. Seek
Medical advice in
case of continued
irritation.
Seek Medical
Attention in case
of extended
Skin/Eye contact.

Tables of results
Experiment A

Experiment

C4H9Br

Concentration
moldm-3

Initial
temperature

Final
Temperature

Time taken
For solution
to lose colour
(sec)

1 2 3 4 5 1 2 3 4 5 5 1 2 3 4 5

A1
A2
A3
A4
A5
Experiment B
Experiment

NaOH
Concentration
moldm-3

B1
B2
B3
B4
B5

Initial
temperature

Final
Temperature

Time taken
For solution to
lose colour
(sec)
1 2 3 4 5 1 2 3 4 5 5 1 2 3 4 5

Initial
temperature

Final
Temperature

Experiment C
Experiment

C1
C2
C3
C4
C5

Temperature

Time taken
For solution to
lose colour (sec)
2 3 4 5 1 2 3 4 5 1 2 3 4 5

Experiment D
Experiment

D1 - LiCl
D2 - NaBr

Temperature

Initial
temperature

Final
Temperature

Time taken
For solution to
lose colour
(sec)

2 3 4 5 1 2 3 4 5 1 2 3 4