Chemistry Individual Investigation

By Adrien Wald

Research Question
How does the rate of reaction of the iodination of acetone change by increasing the concentrations
of the reactants and catalyst, and therefore what is the reactions rate expression?

Background
The iodination of acetone proceeds by the following generalized stoichiometric reaction, though,
admittedly, in actuality it follows a complex reaction mechanism that simplifies to the reaction shown
below (Mork):
" + & &

)*

+ & "

As can be seen, there are two reactants, iodine and acetone, and the reaction is catalyzed by protons or
hydrogen ions. In this investigation, the iodine and acetone were in aqueous solution (0.005M and 4M
respectively) and the hydrogen ions were acquired from hydrochloric acid in 1M solution.
The purpose of this investigation is to determine the rate expression for the iodination of acetone. Rate
expressions may not be determined through theoretical means and therefore require experimental trials
to be deduced. The rate expression of a stoichiometric reaction relates the concentrations of reactants,
catalysts and sometimes even products to the rate at which the reaction will proceed. A typical rate
expression may look something like this:
=

where , and are the concentrations in 3 of different species and , and are coefficients
that usually take on small positive integer values, but may, according to Mork, sometimes take on
negative or half integer values (e.g. -1,1/2,-1/2) (Mork). The rate expression constant, , is different for
every reaction and changes with temperature according to the Arrhenius equation. However, when
calculating the rate expression coefficients, it is not necessary to know , as it is eliminated in the
calculation, as shown below:
>
=
"

2
>
2
"

4
>
4
"

5
>
5
"

2
>
2
"

4
>
4
"

5
>
5
"

and when only one concentration is changed - lets assume we change the concentration of species everything else cancels out and one is left with:
>

=
"

for

>

2
>
2
"

4
>
4
"

5
>
5
"

= " &

>

2
>
2
"

>

"

"

Substituting the values for the rates and concentrations of these species, we can determine the value of
the rate expression coefficient, , by rearranging:

 = log

CD
CE

>
"

By varying the concentration of each species taking part in the reaction, one can then construct the
complete rate expression, by identifying the coefficients. The last step is to calculate the value of the
rate constant, . This can be done by substituding the concentrations of all species and the rate of
reaction, and then solving for .
The rate will be determined by using the method of initial rates (Mork). The rate of reaction is the
change in concentration of a species over time. For this investigation, since iodine is the limiting
reactant, it will be used to measure the rate.
=

" GHI2J " HIHKH2J

"
=

GHI2J HIHKH2J

Because iodine is the limiting reactant, the final concentration of iodine is zero. The initial time is also
zero. The formula for the rate therefore becomes:
=

" HIHKH2J

Motivations
Chemistry is a highly complex and interesting area of active research. Intending to study biochemistry,
as an undergraduate course, I decided that pursuing an investigation in the organics section of chemistry
would be most beneficial to my future studies. Looking at how organic molecules interact with other
species is important in biochemistry and especially in pharmacology, as many drugs are synthesized by
multiple nucleophile attacks and substitutions. The iodination of acetone is an example of a bimolecular
nucleophilic substitution (Farmer). In the beginning, I was intending to use a photo spectrometer, but it
turned out none was available. Learning to use a tool such as this would most certainly have been a
useful experience, which I could have applied to my future studies.

Hypothesis
The iodination of acetone is a specific example of a class of reactions termed alpha halogenations, in
this case of ketones. Alpha halogenation occurs in organic compounds containing a carbonyl group,
where the hydrogen is bonded to the carbon, which is directly adjacent to the carbonyl group
(Farmer). A halogen acts as a nucleophile and substitutes one of the hydrogens in an SN2 attack
(Farmer). However, prior to the substitution, the ketone must undergo a tautomerization reaction, where
the keto isomerizes to an enol. The tautomerization of acetone to its enol form is an equilibrium reaction,
favoring the keto form (Ashenhurst). This is because the keto form is more thermodynamically stable
with bond enthalpies summing at 1500 Q> , compared to the 1452 Q> of the enol form
(Ashenhurst). As such, in water at standard conditions, the equilibrium constant of the tautomerization
reaction is ~1 10QU (Ashenhurst). Therefore, by Le Chateliers Principle, increasing the concentration
of acetone will shift the equilibrium to the right. According to the generally accepted reaction
mechanism of the iodination of acetone, the steps after the equilibrium reaction are fast. Therefore, the
tautomerization being part of the whole reaction mechanism, and its product being necessary in the
succeeding steps, one can say, with certainty, that acetone is of order greater or equal to 1. Also, it is
important to realize that since the enol form reacts in the iodination step, the product of the rightward
reaction of the equilibrium is constantly being removed. Moreover, the tautomerization of acetone relies
on the presence of hydronium ions (& V ), or (less specifically) protons, to proceed. This is because
in the tautomerization, a proton forms a dative covalent bond with the oxygen on the carbonyl group,

after which a molecule of water accepts a proton from the carbon, thereby causing the formation of a
double bond between the carbon and the carbon on the carbonyl group. This in turn causes the double
bond between the oxygen and carbon of the carbonyl group to turn into a single bond, effectively
forming a hydroxide group. (Understanding derived from a diagram, see Appendix 1) It is therefore
that I assume that hydrochloric acid will be a reactant of order 1 or greater. Lastly, since iodine is
required in a fast step of the reaction, I hypothesize it will be of order 0.

Independent Variable
Range of concentrations for each reactant taking place in the reaction. This is done by changing the
volume of reactants in the mixture and decreasing the volume of water to have a net volume that stays
constant. For acetone and hydrochloric acid (HCl), this is done by incrementally adding 3ml to mixture,
whilst incrementally reducing the water content by 3ml for each run, whilst for iodine, this is done in
4ml increments. Effectively what this does is double and the triple the concentration of all reactants
individually, such that one can assess the effect of increasing the concentration of any one reactant on
its own.

Dependent Variable
Rate of reaction ( Q& Q> ), measured using a timer in , and then converted to rate using the initial
rates method.

Controlled Variables
Table 1: Controlled variables table, describing how and why they were controlled
Variable
Why it was controlled
How it was controlled
Starting of the timer with
Starting the timer after the last
The timer was always started
respect to mixing reactants
drop mixes or when they first
after all the reactants came in
come in contact will have an
contact. Thereby it was
effect on the total time of
important the reactants were
reaction recorded by the timer.
mixed at the same rate each
time.
Rate at which contents of two
Since the timer was started
The beaker was tilted at the
beakers are mixed together
after all of the reactants were in
same speed each time.
one beaker, taking longer to
However, human error does
pour would mean the timer was
play a great part in this, as I
started later into the reaction.
wasnt 100% sure how fast it
was every time.
Batch of chemicals
To avoid potential
To minimize the risk of
concentration differences when
differing concentrations of
making the solution again.
reactants for different trials, the
entirety of solutions needed for
all the trials were prepared in
one go.
Pipettes
Each chemical had its own
Pipettes were labeled and the
pipette to avoid cross
investigator made certain that
contamination of chemicals
the correct pipette was used for
and to minimize concentration
each chemical and that no
deviance from the proper
cross contamination occurred.
values.

Background against which

color was determined.

Temperature of environment

Different backgrounds may

affect the human eyes
perception of color, thereby the
investigator felt it was
important to have the same
background for every trial to
avoid that limitation.
The rate expression constant k
varies with temperature
according to the Arrhenius
equation, therefore, in order to
get correct results, the
temperature of the environment
needs to be controlled.

The back of a black laptop was

used as a background for every
trial. Furthermore, all trials
were carried out in artificial
lighting, so that it was
constant.
The experiment was performed
in a room temperature (294K)
laboratory, which experience
only minor temperature
fluctuations.

Equipment/Apparatus List

Volumetric Flask (2500.5ml) x4

Pyrex Beaker (25ml) x10
Pipette (10ml 0.1ml) x4
Graduate Cylinder (25ml 0.5ml) x1
1M hydrochloric acid (0.01M)
99.9% acetone

Distilled water
Electronic balance (0.01g)
Black background
Stopwatch (1s)
0.05000.0001M iodine solution

Safety & Precautions

Hydrochloric Acid (Material SafetyHydrochloric Acid MSDS)

HCl is an acid and is corrosive. Causes severe burns.

Routes of entry: Skin, eyes, inhalation and ingestion.
When handling HCl, wear goggles and gloves at all times.
If HCl comes in direct contact with skin, wash immediately with water.
Spillage should be cleaned immediately using multiple wet paper towels or water-saturated
cloth.

Acetone (Material Safety Acetone MSDS)

Pure acetone is highly flammable (less in solution).

Irritating to eyes.
Repeated exposure may cause dry skin.
Vapors may cause drowsiness or dizziness.

Iodine (Material Safety Iodine MSDS)

Irritant. Corrosive. Avoid contact with skin and eyes. Wash intensely with water if contact is
made for at least 15 minutes in eyes and skin.
Do not ingest or inhale.
Skin contact can produce inflammation and blistering (Material Safety)
Toxic to thyroid.

Methodology
Preparation
1. Preparation of 250ml of 4M acetone.
a. 58.080.01g of acetone were weighed using a scale, by first placing a 250ml beaker on
the scale, zeroing and adding acetone until 58.08g of acetone were in the beaker. (Note
the molar mass of acetone is 58.08g, therefore 1mol of acetone in a solution of 0.25dm 3
is 4M)
b. The acetone was then transferred into a 250ml volumetric flask.
c. The volumetric flask was then filled to the 2500.5ml mark with distilled water.
d. The flask was then stoppered.
>Y.Y>["%
e. The concentration of this solution was =
= 4.00 0.01 Q&
Y."]YY."YY%

2. Preparation of 250ml of 0.005M iodine solution from 0.05M iodine solution.

a. 25.00.5ml of 0.05000.0001M iodine solution were measured using a 25ml graduate
cylinder.
b. The iodine solution was then transferred into a 250ml volumetric flask.
c. The volumetric flask was then filled to the 2500.5ml mark with distilled water.
d. The flask was then stoppered.
Y.Y]YYY."YY%Y.Y"]Y".YY%
e. The concentration of this solution was =
= 0.0050
Y."]YY."YY%

3.
4.
5.
6.

0.0001 Q&
Preparation of 250ml of 1M hydrochloric acid.
a. 250ml of 1M hydrochloric acid were poured into a 250ml volumetric flask.
b. The flask was then stoppered.
Preparation of 250ml of distilled water.
a. 250ml of distilled water were poured into a 250ml volumetric flask.
b. The flask was then stoppered.
Four 10ml pipettes were labelled acetone, HCl, water and iodine using a sharpie.
Ten 25ml Pyrex beakers were labelled A and B in an alternating fashion (5 of each).

Run description table

Table 2: Showing the ratios of reactants for each respective run. Adapted from (Mork).
BEAKER A
Beaker B
4.0 M acetone
1.0 M HCl
deionized H2O
0.0050 M I2
Run number
(0.1mL)
(0.1mL)
(0.1mL)
(0.1mL)
1
3.0 mL
3.0 mL
8.0 mL
4.0 mL
2
6.0 mL
3.0 mL
5.0 mL
4.0 mL
3
9.0 mL
3.0 mL
2.0 mL
4.0 mL
4
3.0 mL
6.0 mL
5.0 mL
4.0 mL
5
3.0 mL
9.0 mL
2.0 mL
4.0 mL
6
3.0 mL
3.0 mL
4.0 mL
8.0 mL
7
3.0 mL
3.0 mL
0.0 mL
12.00.2 mL*
* The uncertainty is double, because one has to use the pipette twice in order to get 12mL.
This table shows the volume of solutions and distilled water used for each run. By varying the volume
of reactants and distilled water, it was possible to change the concentration of reactants, whilst keeping
the volume constant. Each run will be repeated for a total of 5 trials.

The Experiment
1. Two beakers (one labelled A, the other B) were taken.
2. Using the acetone 10ml pipette, 3.00.1ml of 4.00M acetone were transferred from the
volumetric flask into beaker A. The volumetric flask was stoppered after all transfers.
3. Step 2 was repeated for both the HCl and the distilled water, transferring volumes as indicated
in Table 2, Run 1.
4. Using the iodine 10ml pipette, 4.00.1ml of 0.0050M iodine solution were transferred into
beaker B.
5. Next, the stopwatch was reset (if it wasnt already).
6. Beaker B was placed in front of the black background.
7. With a quick gesture, all of the contents of beaker A were poured into beaker B. As soon as all
of the contents were in one beaker, the stopwatch was started.
8. Once the solution turned clear, the stopwatch was stopped. The human error associated with
this method of determining the end of the reaction is great and this will be extensively discussed
in the Evaluation section.
9. The time was recorded into an Excel spreadsheet.
10. Steps 1 to 9 were repeated four more times for a total of 5 trials.
11. Next, all ten beakers were rinsed and dried.
12. Steps 1 to 11 were repeated for all 7 runs by changing the concentrations of the reactants as
shown in Table 2.
13. Note that for run 7 it is necessary to use the pipette twice, which doubles the uncertainty of the
result.

Raw Data
Table 3: Showing time taking until contents of beaker were clear with respect to each run and trial.
Run number
1
1
1
1
1
2
2
2
2
2
3
3
3
3
3
4
4
4
4
4
5
5
5
5
5
6

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

Time until clear (sec, 1s)

140
141
137
134
133
74
71
71
68
71
50
51
50
42
49
96
68
65
66
67
52
50
51
49
49
272

6
6
6
6
7
7
7
7
7

2
3
4
5
1
2
3
4
5

267
278
278
279
420
412
410
456
411

Processed Data
As the raw data stands, it only shows the time taking until the contents of the beaker turned clear.
However, what is important for this investigation is the rate of the reaction. The rate of reactions is
given in Q& Q> . To calculate the rate of reaction from the raw data, the method of initial rates
is used. As derived in the Background section of this paper, the formula for the rate is given by:
=

" HIHKH2J

The initial concentration of iodine for each run is given in the following table:
Table 4: Showing the initial concentration of iodine for each run number
Run Number
Initial Iodine Concentration (Q )
1
2
3
4
5
6
7

0.00110.0001
0.00110.0001
0.00110.0001
0.00110.0001
0.00110.0001
0.00220.0001
0.00330.0002

Sample calculation showing derivation of values for iodine concentration

Moles of iodine in 4ml of 0.005M iodine solution:
= 0.0050 2.00% Q&
= 0.0040 2.50% &
= = 0.0050 2.00% 0.0040 2.50% = 0.000020 0.000001
Concentration of iodine in 18ml mixture:
=

0.000020 4.50%
=
= 0.0011 0.0001 Q&

0.0180 2.22%

The 2.22% is the sum of the uncertainties of four pipette uses divided by the the volume.
Sample calculation for rate of reaction
Using data point Run 1, Trial 1:
0.0011 6.72%
=
= 7.9 10Qi Q& Q> = 7.9 0.6 Q& Q>
140 0.71%

Applying this calculation to the whole dataset yields the ensuing table:
Table 5: Showing the rate of reaction with respect to each run number and trial.
Run number
Trial
Rate (Q Q )
1
1
1
1
1
2
2
2
2
2
3
3
3
3
3
4
4
4
4
4
5
5
5
5
5
6
6
6
6
6
7
7
7
7
7

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

7.90.6
7.80.6
8.00.6
8.20.6
8.30.6
151
151
151
161
151
222
222
222
262
222
111
161
171
171
161
212
222
222
222
222
8.10.5
8.20.5
7.90.5
7.90.5
7.90.5
7.90.5
8.00.5
8.00.5
7.20.5
8.00.5

Next, we way find the mean rate for each run. Recall the formula to calculate the mean:
=

where is the mean, Un is the nth term and n is the number of terms in the dataset. represents the
summation of all values. Applying this formula to the data point Run 1, Trial 1:
=

7.9 + 7.8 + 8.0 + 8.2 + 8.3 (5 0.6)

Finding the mean for each run yields:

= 8.0 0.6

Table 6: Showing the average rate of reaction with respect to the run number.

Run Number

Average Rate of Reaction (Q Q )

1
2
3
4
5
6
7

8.00.6
161
232
161
222
8.00.5
7.80.5

Now that we have the rate of reaction, it is best to remove the Run column and instead show the
concentrations of each reactant for each run. The initial concentrations in the final mixture are calculated
in the same way as before.
Table 7: Showing rate of reaction and the associated concentrations of reactants.
Acetone
Hydrochloric acid/
Iodine
Average Rate of
concentration
proton concentration
concentration
Reaction
(Q )
(Q )
(Q )
(Q Q )
0.670.04
0.170.01
0.00110.0001
8.00.6
1.330.06
0.170.01
0.00110.0001
161
2.000.07
0.170.01
0.00110.0001
232
0.670.04
0.330.02
0.00110.0001
161
0.670.04
0.500.02
0.00110.0001
222
0.670.04
0.170.01
0.00220.0001
8.00.5
0.670.04
0.170.01
0.00330.0002
7.80.5

Determining the rate expression

The rate expression for the iodination is as follows
= & &

"

One sample calculation is shown for each species and all possible combinations are shown in Table 8,
but without error propagation.
Acetone Order using Run 1 & 2
= log

= log

r)s rtr)s D
r)s rtr)s E

>
"

8.0 0.6
ln(0.50 0.07) 0.7 0.1
= log Y.]YY.Y] 0.50 0.07 =
=
16 1
ln(0.50 0.05) 0.7 0.1
= 1.0 0.3 1

Y.i[Y.Yu
>.&&Y.Yi

Hydrogen Ion Order using Run 1 & 4

= log

)* D
)* x

>
u

 = log

8.0 0.6
ln(0.50 0.07) 0.7 0.1
= log Y.]"Y.Yi 0.50 0.07 =
=
16 1
ln(0.52 0.06) 0.7 0.1
= 1.0 0.3 1

Y.>[Y.Y>
Y.&&Y.Y"

Iodine Order using Run 1 & 6

= log

= log

yE D
yE z

>
i

8.0 0.6
ln(1.0 0.1)
0.0 0.1
= log Y.]YY.Y[ 1.0 0.1 =
=
8.0 0.5
ln(0.50 0.07) 0.7 0.1
= 0.0 0.3 1

Y.YY>>Y.YYY>
Y.YY""Y.YYY>

Table 8: Showing order of reactants derived using the method demonstrated above.
Runs
Species
Calculated Order
Nearest Integer Order
1&2
Acetone
1.0
1
1&3
Acetone
1.0
1
2&3
Acetone
0.9
1
1&4
Hydrogen Ion
1.0
1
1&5
Hydrogen Ion
0.9
1
4&5
Hydrogen Ion
0.8
1
1&6
Iodine
0.0
0
1&7
Iodine
0.0
0
6&7
Iodine
-0.1
0
Thereby, we can deduce the rate expression for the iodination of acetone to be:
= & &

or simply

>

>

"

= & & V

(Determining the rate expression - all uncertainties calculated in percentages (excluding logarithmic),
but displayed as absolute uncertainties in the calculations above and below.)
The last step is to find the rate expression constant, . To deduce it, we will substitute all the data for
each run and take the average of the different values of we get. Note that, unlike when determining
the rate expression exponents, where the difference of units ( vs. ) does not play a role, as
everything is in ratios, when calculating the rate expression constant, it does matter. The decision to
shown the rate in micromoles was taken as it helps to better visualize the data.
=

(8.0 0.6) 10Qi

= (7 1) 10Q] Q> & Q>
(0.67 0.04) (0.17 0.01)

Table 9: Showing the k values derived by substituting into the derived rate expression.

Run

K value

1
2
3
4
5
6
7

(7 1) 10Q]
(7 1) 10Q]
(7 1) 10Q]
(7 1) 10Q]
(7 1) 10Q]
(7 1) 10Q]
(7 1) 10Q]

By taking the mean of all values, we get the rate expression constant to be equal to (7 1) 10Q] or
roughly 7 10Q] . Therefore, the complete rate expression is:
= 7 10Q] & &

>

>

"

Graphs
Linear Regression Line
Calculation (Simple
Linear Regression.)
= +
where is given by
=

~D }~ ~

E
~D }~

th

(H is the term of the

concentration of acetone data,
th
H is the term of the average
rate of reaction data)

and = 0 since, if the

acetone concentration is 0,
there is no reaction.
Substituting, we get
= 11.7
*This formula for linear regression only works if the y intercept is forced at = 0.
Effect of concentration of iodine on the rate
of reaction of the iodination of acetone

30

average rate of reaction (moldm-3s-1)

average rate of reaction (moldm-3s-1)

Effect of concentration of HCl (hydrogen ions) on

the rate of reaction of the iodination of acetone
25
R = 0.98375

20
15
10
5
0
0.00

0.10

0.20

0.30

0.40

concentration of HCl (moldm-3)

0.50

0.60

14
R = 0.75

12
10
8
6
4
2
0
0.0000

0.0010

0.0020

0.0030

0.0040

concentration of iodine (moldm-3)

Conclusion
In conclusion, through this investigation, we were able to derive the rate expression for the iodination
of acetone. We investigated the relationship between concentration of reactants and the rate of reaction.
The graphs, in conjunction with the rate expression, show that the relationship between the
concentration of acetone and hydrochloric acid, and the rate of reaction is linear in nature, whilst the
relationship between the iodine concentration and rate of reaction is non existent, due to its zero order
role in the rate expression. These findings confirm the hypothesis, which was based on theoretical
knowledge, acquired from many sources. In other words, the rate expression derived is consistent with

the proposed reaction mechanism of acetone. However, contrarily to the orders of the reactants, the
value which was found to be roughly 7 10Q] is not consistent with literature. According to Meyer, at
294K, the value is 1.42 10Q& and 7.87 10Q] at 273.2K (Meyer). However, this investigation was
conducted at around 294K, so the derived value is off by 2 magnitudes. In Meyers investigation, the
k value was derived using theoretical means - Activation Energy and the Arrhenius equation - and
therefore it is likely that some other factor must have effected this investigations results. A good way
to test for this would be to do investigate the effect of temperature on the value of the rate expression.

Evaluation
Rank* Error
1
Human error/
determining end of
reaction by eye

Temperature

Precision of
equipment

Not closing the

volumetric flasks
(systematic)

How it affected the investigation

The human eye is subjective, in
that what it recognizes is
dependent on context. For this
experiment, determining
whether the mixture was clear or
not was quintessential and the
human eye is very prone to
error. Thereby, what I may have
recognized as clear, might have
been still reacting, or, on the
contrary, might have been clear
for a while. Since I was
dependent on my eyes to
determine the time until the
reaction was complete, it is safe
to assume the data is not very
accurate.
Temperature raises the average
kinetic energy of the particles.
Particles with higher energy are
more likely to be in collisions
that are successful. In other
words, an increase in
temperature would increase the
rate of reaction, which would
skewer the results.
The precision of equipment
could have been higher. More
precise measurements would
have yielded for reliable results.
It was sometimes the
unfortunate case that I forgot to
close the volumetric flasks. This
had an especially great impact
on the acetone, as it is volatile,
thereby most likely decreasing
the solutions concentration.
Since this investigation relies
heavily on the concentrations of
the reactants, this had a large
impact on the results.

How to fix it
By using a photo spectrometer,
the subjective bias is removed.
However, one was not available
to me and the colorimeter didnt
work properly. Photo
spectrometer can the absorbance
or transmittance of light, so at
100% transmittance the reaction
is over. Using this tool would
have been a much better
alternative to simply using the
eye.

This experiment was conducted

in a school lab which is not
accurately temperature
controlled. However, it is safe to
assume that the temperature
differences were most likely
negligible and only had a minute
impact on the results.
Use equipment that is precise to
more significant figures. For
example, pipettors, more precise
graduate cylinders.
Remembering to close the
volumetric flasks immediately
after use. Preventing loss of
solution through evaporation.

Appendix 1

Fig. 1. Keto-enol Tautomerism. Digital image. Expertsmind.com. ExpertsMind IT Educational Pvt.

Ltd., n.d. Web. 2 Feb. 2016. <http://www.expertsmind.com/topic/properties/ketoenol-tautomerism913334.aspx>.

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