Acetylation of Aniline

135 mL distilled water + 4.5 mL conc. HCl 5.3 g of anhydrous sodium acetate
5.0 g of Aniline +
*Always add acid to water*
30mL distilled water
Dissolve

*Use only clear filtrate (decolorize with activated

charcoal when needed)

Aniline Hydrochloride solution

*with stirring

6.2 mL acetic anhydride

Immediately add,
Stir for 30 minutes

Repeat, if necessary
Cool the solution in ice Obtain a small sample

*Allow to crystallize *Drop in ice-cold water

Filter
Formation of No Formation
Crystals of Crystals
Crude acetanilide
*Continue stirring
 Recrystallization of Acetanilide Prepare filtration setup with
Crystals 100 mL of boiling water FLUTED Filter paper

Dissolve *Wet the filter paper with

HOT water, discard the
+ boiling chips to prevent bumping and loss of flow-through
sample

Remove from heat

+ 1g activated charcoal

*Do NOT add while solution is vigorously boiling,

frothing may occur

Swirl,
boil mixture for 10 minutes
*Keep the funnel warm to
prevent premature
+ HOT water to dissolve
crystallization
any visible crystals

*Avoid excess water to

FILTER prevent recrystallization

Filtrate Residue

Cool to room
TRASH BIN
temperature

Chill in ice
bath, to
crystallize
FILTER

Filtrate Precipitate

Sink Dry between

sheets of Determine Melting point
filter/bond paper

Weigh Submit in WIDE-

mouthed AMBER bottle
Chemical Test

Hydroxamic Acid Test (for Primary Aromatic Amides)

Amide suspend 5 mL water

+ 0.5 mL 3% hydrogen peroxide

+ 2 drops of 5% ferric chloride

Heat to boiling

*If the color fades, continue to add

ferric chloride until it persists

+ Deep burgundy or magenta color