Chemistry Essay

Name _________________________

Period _____ Date ______________

PREPARATION OF TERT-BUTYL CHLORIDE

FROM TERT-BUTYL ALCOHOL

Purpose:

To synthesize 2-chloro-2-methylpropane (tert-butyl chloride) from 2-methylpropan-2-ol (tert-butyl alcohol).

Discussion:

The substitution of a hydroxyl group with a halide follows the SN1 mechanism.

1)

2)

3)

(1) Protonation of the hydroxyl group creates an excellent leaving group – a water molecule. (2) The water leaves, creating a carbocation, (3) which then bonds with the chloride ion to form the product.

The following equipment setup diagrams will be used throughout the procedure. Refer to these as needed.

Figure 1: Separatory Funnel Figure 2: Gravity Filtration

Filter paper

Sep funnel Glass funnel

Iron ring

50 mL Beaker 50 mL Beaker

Ring stand Ring stand

Figure 3: Simple Distillation

Objectives:

In this lab, you will...

1. synthesize 2-chloro-2-methylpropane from 2-methylpropan-2-ol.

2. verify the identity of your product by determining its boiling point.

3. calculate the percent yield of 2-chloro-2-methylpropane.

Safety:

• Wear safety goggles at all times while in the lab.

• Some chlorinated hydrocarbons have been known to be carcinogenic. Do not touch any of the chemicals with your hands. Wash your hands frequently and report any spill immediately.

Materials:

50 mL Beaker Filter Paper (12.5 cm) Ice

400 mL Beaker Ring Stand 12.1 M HCl

125 mL Separatory Funnel Small Iron Ring tert-butyl Alcohol

10 mL Graduated Cylinder Simple Distillation Setup Distilled Water

125 mL Erlenmeyer Flask Boiling Chips 1 M NaHCO3

Filter Funnel Anhydrous Na2SO4

Procedure:

1. In the fume hood, pour 30 mL of concentrated HCl into a 50 mL beaker.

2. Cool the...