Lab Report 7

Introduction
Lab 7 focused on the synthesis of an alkyl halide. Alkyl halides are organic
compounds in which a halogen atom, such as chlorine, bromine, or iodine, is
bonded to a carbon atom in an alkyl group. These compounds are widely used as
solvents, refrigerants, and intermediates in the synthesis of other organic
compounds in organic chemistry and industry. They are particularly important in
organic synthesis because they undergo substitution and elimination reactions. An
alkyl halide can be produced by reacting an alkene or alcohol with a halogenating
agent such as HCl, HBr, HI, or phosphorus halides. This is known as a substitution
reaction, and it can be unimolecular (only one reagent involved in the transition
state) or bimolecular (two reagents involved in the reaction state). The relative
stability of the carbocation intermediate formed determines the type of substitution
reaction, with tertiary carbocations being the most stable and primary carbocations
being the least stable. Primary alcohols undergo SN2 reactions, tertiary alcohols
undergo SN1, while secondary alcohols undergo both SN1 and SN2 reactions. The
purpose of the lab was to synthesize t-butyl chloride from t-butyl alcohol using SN1
substitution reaction while reinforcing the use of distillation and extraction in
organic synthesis. Also, lab 7 sought to utilize a chemical reaction as a test system
for the presence of a functional group.

Experimental
Lab 7 began with wearing safety equipment such as gloves, goggles, and an apron.
Then the distillation apparatus with a 100mL distillation flask and 25mL receiving
flask was set up as instructed. 10mL of t-butyl alcohol and 20mL of concentrated
hydrochloric acid were added to the distillation flask using a glass funnel along
with a few boiling chips and the rheostat was set to ¼. Once boiling began, the
heating was controlled so that the distilling vapor stayed between 55°C - 60°C. The
distillate was collected until it reached 25mL and the temperature on the
thermometer dropped. Next, the distillate was transferred to a separatory funnel
using a glass funnel along with 15mL of saturated sodium bicarbonate solution and
the funnel was inverted and vented frequently. The separatory funnel was returned
to the ring stand and allowed to form layers within the solution. The aqueous layer
(bottom layer) was drained into a beaker and set aside. Then the organic layer was
extracted with 15mL of water to remove any residual bicarbonate. The organic
layer was collected in a small Erlenmeyer flask, a spatula tip of magnesium sulfate
was added to dry it, and it was covered with a watch glass for 5 minutes in the
hood. The mass of an empty 50mL beaker was measured and recorded in the
observations section. Once a white solid had clumped at the bottom of the flask,
the product was decanted into the pre-weighed beaker. The mass of the beaker with
the product was also measured and recorded in the observations section. Then the
recovered quantity of t-butyl chloride as well as the percent yield was calculated.
For the silver nitrate test, two test tubes, a test tube rack, and a small quantity of t-
butyl alcohol were gathered. Then 1mL of silver nitrate/ethanol solution was added
to each tube. 5 drops of t-butyl alcohol were added to the first test tube and 5 drops
of t-butyl chloride were added to the second test tube. The tubes were swirled
gently and then observations were recorded. Once all experiments had ended, the
aqueous layer and magnesium sulfate solid were disposed of in the sink. The t-
butyl chloride product and silver nitrate test solutions were disposed of in the
halogenated organic waste bottle. Then all glassware was washed, dried, and
returned to their respective drawers.

Results and Discussion

The distillation temperature range was between 40°C - 46°C. The solution of
t-butyl alcohol and hydrochloric acid began boiling around 40°C and the distillate
was dripping into the receiving flask very slowly. At 43°C, the vapor started
condensing at a quicker rate and around 46°C, the distillate had reached the 25mL
mark in the receiving flask. After this, the rheostat was turned off and the distillate
was collected until the temperature dropped and the distillate stopped dripping
because the solution in the distillation flask would have been distilled to dryness
otherwise. After the distillation process ended, the total amount of distillate
collected was around 30mL.
The product was extracted with sodium bicarbonate and water to neutralize
traces of acid present in the organic layer.
 The moles of t-butyl alcohol and hydrochloric acid used in the experiment
were found using their respective volumes, molecular weights, molarities, and
densities. There were 0.105 moles of t-butyl alcohol and 0.24 moles of HCl used.
The limiting reagent was t-butyl alcohol because it was the reactant with the
smallest number of moles. The theoretical yield was calculated using the moles of
t-butyl alcohol in a 1:1 ratio. The empty beaker weighed 28.418 g, while the
product-filled beaker weighed 34.813 g. Subtracting these values yielded the
product's mass, which was determined to be 6.395 g. After that, the percent yield
was calculated by dividing the actual yield by the theoretical yield and multiplying
by 100. The percent yield was determined to be 65.79%. This could have been due
to loss of product during transfers and procedural mistakes.
Quantity of HCl used: 20mL
0.02 L 12 moles
Moles of HCl used: 1
×
1L
= 0.24 moles

Quantity of t-butyl alcohol used: 10mL

10 mL 0.781 g 1 mole
Moles of t-butyl alcohol used: 1
×
1 mL
×
74.12 g
= 0.105 moles

Limiting reagent: T-butyl alcohol.

0.105 moles 92.57 g
Theoretical yield of t-butyl chloride: 1
×
1 mole
= 9.720g

Actual yield (mass of product): 6.395g

6.395 g
Percent yield: 9.720 g ×100 % = 65.79%

Two test tubes that contained 1mL of silver were observed during the silver
nitrate test. The first tube in which 5 drops of t-butyl alcohol were added showed
no change. This was because there was no tertiary halide present. Cloudy white
solid (silver chloride) was observed after 5 drops of t-butyl chloride were added to
the second test tube. The presence of white solid confirmed the presence of a
tertiary halide (t-butyl chloride) in the second test tube.

Conclusion
The objective of lab 7 was accomplished. T-butyl chloride was synthesized
successfully with a percent yield of 65.79% which could have been caused by
experimental errors and loss of product during transfers. The distillation
temperature range was found to be between 40°C - 46°C. Cloudy white solid was
produced which confirmed the presence of t-butyl chloride as a tertiary halide. The
information gained from experiment could be useful when trying to demonstrate
the mechanism of an SN1 reaction and show the presence of a certain functional
group in the future.