Preparation of a T-Butyl Chloride From

T-Butyl Alcohol Lab

Morgan Felix & Lakin Smith

April 29, 2020

Due May 4, 2020

Discussion

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The purpose of this lab is to synthesize 2-chloro-2-methylpropane (tert-butyl
chloride) from 2-methylpropan-2-ol (tert-butyl alcohol). This lab works using an S 1, or
substitution nucleophilic unimolecular, mechanism. This means that there is one

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molecule undergoing a change during the rate-determining step of the mechanism. In
this reaction, tert-butanol reacts readily with HCl and forms tert-butyl chloride. In S 1
mechanisms, a nucleophile replaces a leaving group. In this lab, the hydroxyl group with
a halide can protonate into an H2O molecule, which is the leaving group. This makes
the water molecule form a carbocation where the hydroxyl was bonded at first. This
helps to form the product (tert-butyl chloride). The picture below shows the reaction that
happens in this mechanism.

In this lab, HCl will be put into a beaker then cooled to 5°C. The cooled HCl will
be poured into a separatory funnel. A separatory funnel is a piece of equipment that
consists of a pear shaped glass body with a stopcock and a stopper on the top. This
allows for clean separation of two liquids. In this case, the two liquids being separated
would be water from the tert-butyl chloride. The amount of tert-butyl chloride will be
recorded by adding 2 g of sodium sulfate to ‘dry’ it. Using a simple distillation apparatus,
the boiling point will be determined. A thermometer is attached to the top to measure
the boiling point. The distillation apparatus works by allowing the product to heat up to
whatever its boiling point is. The tert-butyl chloride will evaporate, causing it to
condense into a liquid. The apparatus is used instead of a Dennis tube because of the
difference in boiling points in tert-butyl chloride and sodium sulfate. The distillation
apparatus takes less time.
This discussion was made using rsg.org, chem.uwi mona.edu, and
chem.ucla.edu.

Procedure
Materials
● 50 mL Beaker
● 400 mL Beaker
● 125 mL Separatory Funnel
● 10 mL Graduated Cylinder
● 125 Erlenmeyer Flask
● Filter Funnel
● Filter Paper (12.5 cm)
● Ring Stand
● Small Iron Ring
● Simple Distillation Setup
● Boiling Chips
● Ice
● 12.1 M HCl
● Tert-butyl Alcohol
● Distilled Water
● 1 M NaHCOვ
● Anhydrous NaշSOч

Procedure
1. In the fume hood, pour about 30 mL of concentrated HCl into a 50 mL beaker.
2. Cool the concentrated HCl to 5℃ in an ice bath (400 mL ⅓ full of ice and tap
water).
3. Pour the cooled HCl into a 125 mL separatory funnel.
4. Add 10.00 mL of tert-butyl alcohol and gently shake the mixture. After shaking,
invert the sep funnel and open the stopcock to relieve pressure. Be sure to point
the bottom of the sep funnel away from yourself. Repeat this every 30 seconds
 for 5 minutes. Let the solution stand for another 15 minutes, relieving pressure
every few minutes.
5. After the 20 minutes, allow the mixture to stand undisturbed until the layers have
separated. Place the 50 mL beaker under the stopcock on the sep funnel,
remove the stopper from the sep funnel, and drain the bottom aqueous layer into
the beaker. Close the stopock.
6. Add 5 mL of distilled water to the sep funnel. Gently shake, allow to stand and
seperate, then drain the water layer into the beaker.
7. Repeat step 6 with 1 M NaHCOვ , then again with 5 mL of distilled water.
8. Transfer the product to a 125 mL Erlenmeyer flask and add about 2 g of
anhydrous NaշSOч.
9. Gravity filters the ‘dried’ tert-butyl chloride product. Record the volume of the
tert-butyl chloride obtained.
10. Determine the boiling point of the product to verify its identity using a simple
distillation setup. This will prevent any open evaporation of tert-butyl chloride.
11. Record today’s atmospheric pressure.

Data
Data Collected from Synthesizing Tert-butyl Chloride from Tert-butyl Alcohol
Volume of Product (mL) Atmospheric Pressure (mmHg) Boiling Point of Product (℃)

7.03 719.4 Trial 1: 48.5

Trial 2: 47.8

Calculations

1)
10.00 mL 0.7887 g 1 mol tert-butyl 1 mol tert-butyl 92.57 g 1 mL = 11.70 mL tert-butyl
T-butAl T-butAl alcohol chloride T-butCl T-butCl chloride

1 1 mL 74.12 g 1 mol tert-butyl 1 mol 0.8420 g

T-butAl T-butAl alcohol tert-butyl T-butCl
chloride

2) % Yield=
Actual yield X 100 = 7.03 mL X 100 = 60.1%

Theoretical yield 11.07 mL

 3) Patm= 719.4 mmHg
760 mmHg - 719.4 mmHg = 41 mmHg
41 mmHg 1℃ = 1.6℃

1 25 mmHg
Trial 1
48.5℃ + 1.6℃ = 50.1℃
Trial 2
47.8℃ + 1.6℃ = 49.4℃
4) Average
49.4℃ + 50.1℃ = 49.8℃

2
5) Error
Absolute Error (EA) = | XE-XT | = | 49.8℃ - 50.9℃ | = 1.1℃
Percent Error (E%) = EA x 100 = 1.1℃ x 100 = 2.2 %
XT 50.9℃

Conclusion
The purpose of this lab was to synthesize 2-chloro-2-methylpropane (tert-butyl
chloride) from 2-methylpropan-2-ol (tert-butyl alcohol). In this lab, the volume of the
product was 7.03 mL. The atmospheric pressure was 719.4 atm. The average of the
corrected boiling points was 49.8℃. Using these values, the absolute error was 1.1℃.
To find the percent error, we divided the absolute error by the true value of the boiling
point and multiplied it by 100 to get 2.2%.
Since this experiment was not done hands on by ourselves, we can not
accurately identify certain errors. One of the errors that could have occurred was
improper measuring. If there was not enough product added or separation was not
completely done thoroughly, this could be the reason our result was a little low. There
also could have been equipment issues, but we can’t say for sure.
We are pleased with our results. To improve the results, it would be beneficial to
do it ourselves. We can’t be certain that our results would improve, but it would help
make more sense. We learned how to synthesize tert-butyl chloride from tert-butyl
alcohol. The techniques and skills learned in this lab can be applied to multiple other
situations. One of them is to create geraniol. Geraniol is a fragrance used in perfume.