PREPARATION OF 2-CHLORO-2- 2

METHYLPROPANE 008
INTRODUCTION:
Alcohols can undergo substitution reactions in which the hydroxyl group is replaced
by a chlorine atom. The type of reaction involves fission of the C – O bond and occurs
most readily in tertiary alcohols. The reaction can be considered as the reverse of the
SN1 hydrolysis of a tertiary halogenoalkane.

+ HCl + H2O

2-methylpropan-2-ol 2-chloro-2-methylpropane

AIM:
The aim of this experiment is to calculate the percentage yield of 2-chloro-2-
methylpropane.
CHEMICALS:
• 2-methylpropan-2-ol
• 2-chloro-2-methylpropane
• Concentrated HCl
• Anhydrous Calcium Chloride
• Sodium hydrogen carbonate
• Sodium sulphate
RISK ASSESMENT:

CHEMICAL HAZARD SAFETY

2-chloro-2-methylpropane
Conc. hydrochloric acid
PRECAUTIONS
Highly flammable and Wear eye protection, the
harmful room should be well
ventilated. Wear gloves
Corrosive causes severe If vapour is inhaled,
burns and irritating to the remove the victim to fresh
respiratory system. air to rest.

2-methylpropan-2-ol flammable Wear eye protection and

Anhydrous Calcium Chloride
Sodium hydrogen carbonate
Sodium sulphate
safety goggles when
dealing with these
chemicals.
Irritant particularly on Wear gloves and goggles
moist skin to protect hands and eyes;
avoid inhalation.
Low hazard, Irritant Wear gloves and eye
protection. Do not eat, it is
irritating.
Low hazard, Irritant Wear gloves and eye
protection. Do not eat it, it
is irritating.

DERRICK ABAITEY
 PREPARATION OF 2-CHLORO-2- 2
METHYLPROPANE 008

APPARATUS:
Separating funnel
Clamp stand
Thermometer
Distillation flask
Condenser
Small measuring cylinder
Bunsen burner

METHOD
Use a 100 cm³ separating funnel and check that the stopper and tap are greased.
Add 12.5 cm³ of 2-methylpropan-2-ol into it.
Then add 35 cm³ concentrated hydrochloric acid, be extra careful when adding it.
Add 2g of anhydrous calcium chloride to it.
Then shake the separating funnel for 2min, while releasing the pressure continuously.
Stand the mixture in separating funnel; you will see two layers formed. Discard the
aqueous layer. Leaving the organic layer in the separating funnel, add 5 cm³ of 5% of
sodium hydrogen carbonate.
Discard the aqueous layer, wash organic layer with 5 cm³ of water.
Discard the aqueous layer.
Transfer to a quick fit tube, and add 2g of anhydrous sodium sulphate, and shake for
2min.
Set up a simple distillation. Decant the product into a pear-shaped flask and distil,
collecting the fraction boiling between 49 and 51. Measure the volume of the product
and use this will be used to calculate the % yield.

Volume of 2-methylpropan-2-ol used = 12 cm³

Density of 2-methylpropan-2-ol = 0.79 cm³

ESTIMATING PURITY
The purity of this experiment will be
determined by the process of
distillation. Distillation is a widely
used method for separating mixtures
based on differences in the
conditions required to change the
phase of components of the mixture.
To separate a mixture of liquids, the
liquid can be heated to force
components, which have different
boiling points, into the gas phase.
The gas is then condensed back into
liquid form and collected. Repeating
the process on the collected liquid to
improve the purity of the product is
called double distillation.

DERRICK ABAITEY
 PREPARATION OF 2-CHLORO-2- 2
METHYLPROPANE 008
This method was used to determine the purity of the product. More information added
on in the evaluation and conclusion.

CONCLUSIONS:
After carrying out this experiment, I found out that, that the actual volume of 2-
chloro-2-methylpropane produced was very little. We should have gotten more than
this value. According to the experiment procedure, the boiling point of the fraction
has to be between 49 and 51ºC. But when we were doing the experiment, due to the
small volume of organic layer we had, we couldn’t get much of the 2-chloro-2-
methylpropane between the specific temperatures. Therefore we exceeded the
temperature to 59 ºC. This affected the volume of 2-chloro-2-methylpropane
produced.

BOILING POINT
Below are the methods used to determine the boiling point of my
product? To be able to determine the boiling point of the product
you have to follow this method;
1. You will have to transfer the liquid under test to the narrow
bore ignition tube to give a depth of about 1 cm.

2. Place the inverted capillary tube in the ignition tube and

attach to the side of the thermometer using a rubber band.

3. Insert in the Thielé apparatus or clamp in the water bath.

4. Heat gently whilst stirring the water in the bath until a steam
of bubbles rises from the bottom of the capillary tube.

5. Remove the heat sources and record the boiling point as the
temperature at which the liquid recedes into the capillary tube.

EVALUATION:
Many things went wrong in this experiment, which would be improved next time if it
was to be done again. Even though we got the 2-chloro-2-methylpropane that we
wanted, but there are affections to the purity. Errors in this experiment will be
explained:

DERRICK ABAITEY
 PREPARATION OF 2-CHLORO-2- 2
METHYLPROPANE 008
Merit

Yield: Factors affecting the yield (errors)

• The volume of 2-methylpropan-2-ol used

According to the experiment procedure, we are meant to use 12.5 cm³ of this
organic compound, but when we measured it, it was not up to the actual volume.
Therefore we had to use whatever volume of it we had. This therefore affected the
yield of the organic layer.

• Shake the reaction gently

When I was shaking the mixture, I was scared that the pressure will build up more
and explode the separating funnel; therefore I left it open most of the times. I
spilled a little bit of the chemical in the funnel, since the funnel was opened;
therefore it also affected my yield.

• Discard the aqueous layer

When discarding the aqueous layer, I probably had some small amount of organic
layer in it, because there were bubbles in the funnel anytime I shake it. Therefore I
had to discard it like that, so I think it’s also affected my yield.

• Wash the organic layer with water

Again, in this stage, some of the organic layer was lost, this was because when we
added the water to it, in the shaking we had some bubbles in it, and hence it made
it very difficult to discard the aqueous layer. When we discard it we had a little bit
of organic layer in it.

• Transfer the product into a quick fit tube

When transferring the product into the quick tube, there was some tiny amount of
product left in the separating funnel, which we couldn’t take out, this can also
affect the yield.

• Collecting the fraction boiling between 49 and 51ºC

We couldn’t work between these ranges of temperature, this is because the
product we had after the distillation was very small, and I got 2 cm³ of the
distillate. Which was very small, therefore I had to keep the distillation running
until I got 4 cm³, the temperature that I got to was 59 to 61ºC. This was far from
the actual temperature that I was meant to use.

DERRICK ABAITEY
 PREPARATION OF 2-CHLORO-2- 2
METHYLPROPANE 008

Purity
Contamination: Contamination was the main source of impurity in the experiment, in
most of the steps in the method, I had to add other chemicals to the organic layer and
separate it again, and therefore I assume there might be some of the aqueous layer
which was to be discarded in the organic layer which is need. I added about three or
four chemicals before I completed the experiment, hence high in contamination.
When swirling the separating funnel around, before discarding the aqueous layer,
there was always bubbles on the line, therefore I couldn’t see the separation properly.
The only way I could discard was to see the chemicals in two layers, which, in my
experiment was not clear enough; therefore I discarded it with the bubbles left in the
organic layer.

Distillation apparatus: Even thought the apparatus might have been washed, I
assume there might be some dirt left in there, which can also affect the purity of the
organic layer.

Organic layer dried up: During the distillation, when I started heating the organic
layer to about 59°C, I lost all the chemicals in the distillation flask. The only thing
that was left in the flask was the anti-bumping granules which were added. This might
also affect the purity of the chemicals, because there might be some impurity in the
organic layer which was collected as well. Since different chemicals have different
boiling and melting point, so as applied in fractional distillation, we collect chemicals
according to its boiling point, therefore after the first collection; the beaker has to be
change, to collect the other chemicals at different boiling point, this was not done in
my experiment, we exceeded the boiling point of the organic layer, which made us
collect all the other chemicals as well including any impurities.

DERRICK ABAITEY
 PREPARATION OF 2-CHLORO-2- 2
METHYLPROPANE 008

Distinction
How to make minimise the errors and make the yield higher.

The volume of 2-methylpropan-2-ol used

The volume of the chemicals has to be measured correctly according to the
experiment procedures next time. If this volume is low, it affects the yield of the
product you will get at the end of the experiment. Therefore it has to be the correct
volume next time we repeat the experiment. In this experiment, the technicians
measured it out for us to use, hence we got different values when we measured them
again, I recommend in our next experiment we measure it ourselves before we start
the experiment. This will make us know that we done the errors ourselves. I think this
error was cause because the chemicals were measured out from different weighing
balances.

Shake the reaction gently

I think the next time I do this experiment; I will follow the instruction set by the
teacher. To minimise this error I will follow the procedure, and make sure I do as it
says. When shaking the chemicals I had to close the tap and shake it gently on a
frequent pressure release, but I felt so scared about this and spilled the chemicals.

Discard the aqueous layer

This is where my main problem is, and I think I lost a lost of organic layer from this
stage. I reviewed it in the previous pages about how I lost some of the organic layer
for having bubbles in the separating funnel. If this experiment was to be done again,
we as a group will allow just one person to shake the funnel. Because, I think it’s
because everyone was shaking the funnel at different times, that’s why we had so
many bubbles in the line. Therefore I recommend the next time we do experiment like
this, just one person is to be allow shaking it, with much care.

Wash the organic layer with water

Similarly at this stage, we still had the bubbles in it, which we will avoid the next time
we do the experiment. We would keep one person to deal with the separating funnel,
with much care, since it makes difficult to separate the organic layer form the aqueous
layer when there are bubbles.

Transfer the product into a quick fit tube

I think in this case, when we do such experiments, the volume we start with has to be
in excess, and hence we wouldn’t be affected that much with the left over.

DERRICK ABAITEY
 PREPARATION OF 2-CHLORO-2- 2
METHYLPROPANE 008

How to make minimise the errors and make the purity higher.

Distillation:
In distillation the purity of the fractions are very important, therefore when collecting
the fraction in at different boiling point, it has to be at its best purity. Some of the
fractions collected in fractional distillation are cracked into different components as
well; this is why they have to be in their best purity.

Contamination: To minimise the contamination of the organic layer, I could have to

follow the procedures in the experiment and shake all chemicals as I was meant to.
The impurities that mostly occurred in this experiment were, when I was adding up
the chemicals and when I was discarding the aqueous layers. I probably didn’t use a
good technique to do so, and it affected my purity by contaminating some of my
chemicals. This time round, if the experiment was to be done again, I would separate
the chemicals very well to make sure I don’t get any aqueous layer in the organic
layer that I want.

Distillation apparatus: to maintain or get good purity for the chemicals used in the
apparatus, what I could have done was to rinse the apparatus with distilled water the
after I rinse it again with the chemical to be used. This will make the chemicals have a
good purity since it would not be contaminated.

Organic layer dried up: there are more contamination when you exceed the actual
temperature of the chemical you are collecting in the distillation, what happens was,
all the organic layer was condensed in the beaker at the temperature of 59°C, in fact I
exceeded the actual temperature. In the organic layer, I assumed there was some
impurity which I could have gotten rid of, but since the temperature was high, I got all
the impurity in the beaker living the anti bumping granules in the tube.

DERRICK ABAITEY