RECRYSTALLIZATION
to crystallize again
purification technique which is based
on changes of solubility at different
conditions (i.e. temperature)
SOLUBILITY AND
TEMPERATURE
Solubility is affected by
Nature (polarity) of the solute and
solvent
Like dissolves like
Temperature
Solubility Temperature
EXPERIMENT 4:
RECRYSTALLIZATIO
N
Selection of the
Recrystallizing
Solvent
Synthesis of
Acetanilide
Purification by
Recrystallization
SELECTING THE
RECRYSTALLIZING SOLVENT
Solvent
Room
Temperature
Hot H2O
Bath
Ice Bath
dH2O
Insoluble
Soluble
Insoluble
Hexane
Insoluble
Insoluble
Insoluble
Ethanol
Soluble
Soluble
Soluble
SYNTHESIS OF
ACETANILIDE
+
Aniline
Acetic
anhydride
+
Nphenylacetamide
/
acetanilide
N-acylation
Nucleophilic Aromatic
Substitution
Acetic
acid
THEORETICAL YEILD
Maximum theoretical amount (in
grams) of product that can be
produced from the reaction
Dictated by the LIMITING REAGENT
the reagent which is completely
consumed at the end of the reaction
DETERMINATION OF THE
LIMITING REAGENT AND THE
THEORETICAL YIELD
Amount
SOLUBILITY
Like dissolves like
Some organic compounds exhibit
partial solubility
temperature, solubility
ACETANILIDE/N-PHENYL
ACETAMIDE
Functional groups
Phenyl (hydrophobic)
Amido (hydrophylic)
RECRYSTALLIZATION IN THE
PURIFICATION OF ACETANILIDE
Synthesis of acetanilide produces:
Acetanilide (slightly soluble in water)
Acetic acid (soluble in water)
Co-product of acetanilide
Product of excess acetic anhydride and H2O
RECRYSTALLIZATION IN THE
PURIFICATION OF ACETANILIDE
Crude Acetanilide
acetanilide +
impurities
heat
+ activated
charcoal
hot filtration
Residue
Filtrate
acetanilide + soluble
impurities
ice bath
filter
Filtrate
Residue
water-soluble
impurities
Pure acetanilide
QUANTITATIVE ANALYSIS
END