Name: John Christopher A.

Pilapil
Lab Partner: Hasmin Lisa H. Corpuz

Date Performed: December 8, 2009

Experiment 6:
Synthesis of an Alkyl Halide
I. Objective(s)
This experiment aims to properly and comprehensively illustrate the reaction that occurs between
alcohols and hydrogen halides by means of demonstrating the synthesis of alkyl halides.
II. Schematic Diagram of the Procedure
A. Materials and Apparatus
Tert-butyl alcohol
Conc. HCl
Solid NaHCO3
Ice Bath

Separatory funnel (30 mL)

distillation set-up (semi-micro)
Erlenmeyer flask (50 mL)
Thermometer

Bunsen burner
Oil bath
Rubber tubing
Aluminum foil

B. Procedure

10mL tert-butyl alcohol and

20mL cold conc HCl

Add a few boiling chips.

Distill the crude tert-butyl

chloride.

Place in 30 mL separatory
funnel. Swirl. Note: Do not
shake.

Decant into a dry, 25-mL

round bottom flask.

Allow mixture to stand for 20

minutes. Open stopcock from
time to time to relieve
pressure.

Dry collected filtrate with small

amount of anhydrous calcium
chloride.

Collect pure tert-butyl chloride

in 10-mL grad cylinder cooled
in ice bath.

Collect the fraction that boils

at 49-52 C.

Submit product in a labelled

vial to instructor.
Separate the layers. Facilitate
separation by +3-5 mL 6M
NaCl soln.

Swirl. Afterwards, decant into

another dry flask.

Discard
aqueous
layer.
Determine aq. layer by adding
1-2 drops H2O. Layer where
water dissolves = aq.

Transfer organic layer into a

dry flask with small amount of
solid sodium bicarbonate.

III. Table of Reagents/Products

Reagent
Tert-butyl Alcohol

Structure

Physical Properties

Hazards

Melting Point: 25 C
Boiling Point: 83 C
Density: 0.78 g/mL
Appearance: colorless liquid
Chemical Formula:

Stable but highly flammable;

may cause irritation when
inhaled and comes in contact
with skin, eyes.

Hydrochloric Acid

Sodium Bicarbonate

H--Cl

(CH3)3COH
Melting Point: -74C
Boiling Point: 53C
Density: 1.18g/mL
Appearance: colorless fuming
liquid
Chemical Formula: HCl
Melting Point: 60 C
Boiling Point: N/A
Appearance: White
crystalline powder.
Odor: Odorless

Corrosive; fatal if enters the

body; burns all body tissue

Inhalation may cause

coughing and sneezing;
extremely large oral doses
may cause gastrointestinal
disturbances.

IV. Waste Disposal

Dispose the aqueous solutions by diluting them first before pouring them into the sink. Any
remaining organic compounds should be disposed into appropriate waste containers.
V. Set-up/s
Preparing a Simple Distillation Apparatus:
1. Let water flow through system
2. Place thermometer below the side arm of distillation head
3. Choose a round bottom flask which the sample fills 1/2-2/3 its volume.
4. Regulate temperature with water or oil bath.
5. Place the sample inside flask
6. Add 2-3 boiling chips or sticks into flask.
7. Turn water supply on and check the water flow through condenser.
8. Heat sample in flask to a gentle boil.
9. Adjust flame so that the rate is 2 drops/sec
10. Discard 1st mL
11. Collect fraction that distills at a constant temp.
12. Remove heat when sample boils