EXPERIMENT 7

EXPERIMENTAL PROBLEM
Halogenation of acetanilide
Educational Purpose
Derivatisation to analyse what is the starting material (phenol or aniline)
Mechanism
Report the percentage yield
Limiting reagent
Predict the product
Understand utility of each reagent

What to Turn In

Sample, report

Requirements: Conical flask, filter paper, buchner funnel, measuring cylinder, stirrer plate,
magnetic bead, ice bath

Procedure:

•   Prepare bromine (0.2 mL) (MSDS: Fatal if inhaled, causes severe skin burns and eye
damage, toxic to aquatic life) solution in glacial acetic acid (4 mL) and dissolve acetanilide
(0.3 g) in glacial acetic acid (1.4 mL). Cool it in ice bath
•   Add prepared bromine solution dropwise to the above acetanilide solution keeping it in
ice bath
•   After complete addition of bromine solution, allow the reaction mixture to stir for 15-20
minutes at room temperature.
 •   Pour it into ice cold water. To remove orange colour, just add enough saturated sodium
bisulfite solution (take help of instructor)
•   Filter the product and wash with cold water
•   Recrystallise from alcohol
•   Record m.p. of recrystallized dry sample
•   Calculate and report the yield.

Evaluation Sheet
Halogenation of Acetanilide

Name ___________________________________Lab Day/Time ______________

Points possible Number of

for this points you
experiment received
(10)

Prelab 0

Postlab 0

Data and Calculations

Procedure
•   Results reporting with recrystallized sample and 1+3+3
•   m.p, tlc plates etc. and analysis
•  

Notebook
1
•   Guidelines for a good notebook are met.

Viva 2

Miscellaneous 0

TOTAL 10