T Pentyl Chloride Lab Report

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Synthesis of t-Pentyl Chloride


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):



Table of Reactants and Products:

CompoundFormula weightVolume used (mL)Weight used (g)Moles usedMoles requiredOther data t-Pentyl alcohol88.15 g22.00 mL---00.20 moles1Density: 0.81 g/mL

HCl36.46 g50.00 mL---00.61 moles1Density: 1.18 g/mL

t-Pentyl chloride106.59 g17.00 mL---00.14 moles

1Density: 0.86 g/mL

Limiting Reactant Calculations:

Theoretical Yield:

Actual Yield:

Percent Yield:

Boiling point analysis:
According to Dr. Edward Kluger, by a temperature of 79-84°C, the product is expected to boil (pg. 20). At about 80°C, the product began to stabilize. This matches the expected boiling point for the product. After simple distillation and measurement, a total of 17 mL of the product was obtained.

Side Reactions:

Summary of experiment:

The following experimental procedure was directed from Introduction to Organic Lab Techniques CHM2211L Coursepack by Dr. Edward Kluger found on pages 18- 20.

Using 22 mL of t-Pentyl alcohol and 50 mL of 37.3% concentrated HCl, a mixture was created and swirled in a 125 mL separatory funnel. After the solution had been mixed for...
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