Kaitlin Webb
Chemistry 112 write up
Experiment #3
Synthesis of t-butyl chloride
In this experiment they had to chill a separatory funnel in ice water. Then cool 37.0mL of
concentrated HCl to about 5 degrees Celsius. They then drained the ice water from the funnel
and added the cooled HCl solution. Then they added 9.50mL of t-butyl alcohol. She shook the
combined HCl solution and t-butyl alcohol in the funnel for 20 minutes, stopping periodically to
open the stopcock to release any pressure build up. After the 20 minutes she then drained the
lower aqueous layer from the funnel into a beaker.
She then added in the funnel successively 5mL of water, then 5mL of 5% sodium
bicarbonate and a second 5mL portion of water. For each wash they had to shake the funnel
several times and again release the pressure. They then had to drain the lower aqueous layer from
the funnel again. The washes dissolved and removed any unreacted t-butyl alcohol. After the
washes they then collected the material in the funnel by pouring it into a beaker and adding 1.0
grams of Magnesium sulfate. This removed any remaining water from the solution. Then they
had to remove the Magnesium sulfate by gravity filtration into another pre-weighed beaker. Then
had to determine the mass of the product formed. They then had to test the reactivity of of the
various substances by placing silver nitrate in five clean test tubes. They added 2-3 drops of their
organic product to the first and observed the results. To the remaining four test tubes they added
n-butyl chloride, sec-butyl chloride, known t-butyl chloride, and t-butyl alcohol. They the
recorded the results.
The theoretical yield of t-butyl chloride is as follows. 7.5 grams x 1 mol t-OH/74.12g tOH x 1 mol t-Cl/ 1 mol t-OH x 92.57 grams t-Cl/ 1 mol t-Cl equals 9.37 grams t-butyl chloride.
They then calculated their percent yield by dividing their mass 8.15 grams of t-butyl chloride by
9.37 grams of the theoretical yield and timed it by 100%. This resulted in a percent recovery of
86.98%. The test tubes showed that the one that reacted just like our sample was the t-butyl
alcohol and there our substance was t-butyl alcohol.