Synthesis of an Alkyl Halide: tert-Amyl Chloride


CH3CH2C(OH)(CH3)2 + HCl   →   CH3CH2C(Cl)(CH3)2 + H2O





  Mix 7.5 mL of tert-amyl alcohol and 20 mL of concentrated hydrochloric acid in a stoppered 125 mL separatory funnel. Shake and vent for 5-7 min.


  Allow the mixture to separate into two layers. Remove the aqueous layer. (How can you tell which layer is the aqueous layer?) Drain the organic layer into a dry Erlenmeyer flask containing a small amount of anhydrous sodium bicarbonate. Swirl the flask to remove any residual acid.

  After all effervescence has ceased, add another small scoop of sodium bicarbonate. Filter the liquid through a drying pipet containing anhydrous magnesium sulfate into another small dry Erlenmeyer flask. Add a few pellets of calcium chloride. Swirl the flask for a minute or two to dry the crude product.

  Decant the crude product directly into a 10-mL roundbottom flask and equip with a fractionating and distillation head as demonstrated in pre-lab. Distill and collect the product from 80 - 88 C into a small, dry graduate cylinder.


  Analysis: Report the actual, theoretical, and percent yields (density of tert-amyl alcohol is 0.81 g/ml and of tert-amyl chloride is 0.87 g/mL). Record an IR spectrum of your product. Compare and contrast the IR of the starting material and the product.