Using SN1 reaction mechanism with hydrochloric acid, t-Pentyl alcohol was converted to t-Pentyl chloride in an acid catalyzed reaction. The reaction took place in a separatory funnel designed to separate immiscible liquids. The crude product was extracted by transferring a solute from one solvent to another. The process of washing the solutions by phase transfer was used in order to remove impurities from the main solvent layer. Finally, the crude product was dried with anhydrous Calcium chloride and purified once more by simple distillation technique.
Results and Discussion:
Main reaction(s) and Mechanism(s):
Mechanism: Table of Reactants and …show more content…
The procedure to purify the crude product was the simple distillation technique found in A Molecular Approach to Organic Laboratory Techniques by Pavi et. al.
1. Aqueous sodium bicarbonate was used to wash the crude t-Pentyl chloride.
a. What was the purpose of this wash?
The purpose of the wash with the basic bicarbonate was to remove the acidic components of the mixture. This helps facilitate the phase separation needed in order to extract the waste and keep the desired product.
b. Why would it be undesirable to wash the crude halide with aqueous sodium hydroxide?
Aqueous sodium hydroxide is a very strong base. By using a very strong base, it can cause the reaction to proceed with the E2 mechanism and gives us undesirable alkene products.
2. Some 2-methyl-2-butene may be produced in the reaction as a by-product. Give a mechanism for its production.
3. How is the unreacted t-Pentyl alcohol removed in this experiment? Look up the solubility of the alcohol and alkyl halide in water.
The unreacted t-Pentyl alcohol is removed by adding water to the mixture. The alcohol will mix into the mixture