EXPERIMENT 8

Title: Synthesis of - Butyl Chloride (2-Chloro-2-Methylpropane)

Objective

The main objective of this experiment is to synthesize tertiary butyl chloride from
tertiary butyl alcohol by substitution nucleophilic unimolecular reaction.

Introduction:

Alcohols can be converted to alkyl halides by means of halogen acid such as

hydrochloric acid hydrobromic acid hydroiodic acid and phosphorus halides such
as pcl3 pbr3 socl3.

There are types of nucleophilic substitution reactions.

SN1 (substitution, nucleophilic unimolecular) and SN2 (substitution, nucleophilic,
bimolecular). SN1 involves a multi-step process whereas SN2 involves a single
step, a concerted reaction.

SN¹ process in this example involves the following: First, the OH (strong base)
group in t-butyl alcohol or t-butanol is not a good leaving group. Therefore, by the
addition of an acid, the OH group will be converted into water (neutral molecule),
which is a good leaving group. Weak bases and neutral molecules are good
leaving groups.

Precautions.

During the entire procedure, we must take care of the following things.
Concentrated hydrochloric acid is highly corrosive and can cause burns thus
must be used with utmost care.

That tertiary butyl alcohol to be used in this experiment is highly flammable and
therefore during the entire setup flames must be avoided anywhere in the
laboratory.
While mixing the compounds in the separatory funnel he always kept the vent
open so that the carbon dioxide formed during the reaction may pass and hence
extra pressure will not be built up in the vessel which otherwise might crack the
glassware.

Procedure:

So firstly we start with taking a record of the regions we are using in this
experiment in a well-defined chart containing their volumes, mass, and molarity,
etc. This chat would be needed at a later face for calculations.

Now we take about 5 ml of tertiary butyl alcohol, which is around 0.052 moles or
3.87 grams. And add about 12 and a half ml of cold concentrated hydrochloric
acid in a separatory funnel.

Giving the funnel a nice mix, we allow the nucleophilic substitution reaction to
take place between both the reagents.

After mixing it for some time we allow it to rest for 15 to 20 minutes so that the
products are made from layers and could be separated.

Once the two layers are completely separated that is the aqueous layer on the
bottom and the organic layer containing our main product in the top, we may pour
down the bottom liquid and separate it as acid waste.
So in the funnel, we are left with the organic solution containing the tertiary butyl
chloride product.

Now we need to watch this layar with a 5% sodium bicarbonate solution to

neutralize the acid.

After adding the sodium bicarbonate we must give the funnel a gentle mix again,
but this time since we are neutralizing an asset with bicarbonate, carbon dioxide
will be evolved in the process therefore the vent should be kept open for the gas
to escape.

Once done we may allow it to rest for some time and hence observe again two
layers, the top one being the desired organic layer, we may pour out the bottom
layer.

Then we need to repeat this washing process but instead of the sodium
bicarbonate, from here onwards we will use distilled water to do the same. Visit
to repeat this step till the time the pH of the solution is neutral.

Once the final amount of organic layer is separated, we must add about 5 grams
of calcium chloride to the solution which will remove any excess amount of water
present in the solution.

Once done we take the final solution into a simple destination set up and allowed
to the distillate.

Tertiary butyl chloride will be the first one to be separated using this method at
about boiling temperature of 49 to 52 degrees centigrade.

After the distillation, we are left with about 3 grams of crystal clear tertiary butyl
chloride.
Observations:

Name of Grams Molecular Moles Name of the

Reactants Weight and Product and
density Moles of the
Product

T - butyl M.W. = 74g

alcohol 3.87 T - butyl
(limiting D = 0.775 g/ml 0.052 Chloride
reagent)
Hydrochloric 11.3 M.W. = 36.5g 0.150 Moles =0.032
Acid (HCl) D = 0.904 g/ml

Name of the Product: T - butyl Chloride M.W. = 92.5g

Theoritical Yield = Lowest Moles of reactant x M.W. of Product

= 0.052 x 92.5
= 4.81 g
Actual Yield = 3.00g

Actual Yield
Yield Percentage = ---------------------------- x 100
Theoritical Yield

= (3 / 4.81) x 100
= 62.37 %

Conclusion:

The nucleophilic substitution reaction is an effective way to synthesize t- butyl

chloride from t- butyl alcohol, within an estimated yield of more than 62%
Post Laboratory Question:

1. In the purification process, the organic layer is washed sequentially with

NaHCO3 and water. What is the purpose of each of these washes?

Ans: After the initial nucleophilic substitution reaction with hydrochloric acid and
then separating the aqueous layer, we are now left with the organic layer
containing our desired product. But however, there are still traces of acid in this
layer. Therefore we use sodium bicarbonate which is a week base that
neutralizes the acid and hence eliminates every last part of acid from the organic
layer.

2. Why anhydrous sodium sulfate is added to the t-butyl chloride in the

purification process? Could solid sodium hydroxide be used instead of anhydrous
sodium sulfate? In the purification process, the organic layer is washed
sequentially with NaHCO3 and water. What is the purpose of each of these
washes?

Ans: Sodium Sulphate (Na2SO4) is added in the Purification process to absorb

the moisture present in the solution. NaOH cannot be used as it will React with t-
butyl chloride & and may change the product.

3. The reaction of t-butyl alcohol and HCI gives t-butyl chloride. Is it SN1 or SN2
reaction and why?

And: In is SN1 because Sn2 reaction doesn’t take place due to static hindrance
at 3-degree carbon and moreover, SN1 is favored due to the formation of a
stable carbocation.

4. Comment on the green chemistry of this experiment. That is, the nature and
amount of solvent (for example water, etc.), and atom economy (number of
atoms in the reactants versus products) in this experiment.

Ans: In this experiment, if we look at the balanced chemical equation, the number
of atoms in the two reactants is the same as the number of atoms in the
products. This means 100% atom economy.