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Synthesis of Acetanilide

Maria Salvacion A. Esmalla, M. Sc.


Department of Biochemistry Faculty of Pharmacy, University of Santo Tomas

Recrystallizatio n
a common and inexpensive purification technique based on the solubility of the desired substance in a single solvent at different temperature

Steps in Recrystallization 1. Choosing the Recrystallizing Solvent


2. 3. 4. 5. 6.

Dissolution of the sample Decolorization (for colored impurities) with activated charcoal Filtration of the hot solution. Cooling the Solution Separating the crystals supernatant liquid.
R G A N I C C H E M I

in

the

Materials and Reagents Hexane Erlenmeyer


Methanol Distilled H2O Aniline Acetic Anhydride flask Beaker Thermometer Iron stand funnel Filter paper

Set-up and Equipment

Proced ure
Selection of recrystallizing solvent The Synthesis Purification

Choosing the Recrystallizing Solvent


1 hexane 2 water 3 - methanol
1 2 3

+ ~2-3 mg of standard acetanilide Note the solubility Solvent Hexane


Soluble Insoluble

SOLUBILITY
Room temperature High temperature

Behavior at Low Temperature

Water Methanol

Cool in an ice bath

Heat in a water bath Note the solubility

Soluble

Insoluble

Cool in an ice bath

Properties of a Recrystallizing Solvent

The compound should be very soluble at the boiling point of the solvent and only sparingly soluble in the solvent at room temperature. The unwanted impurities should be either very soluble in the solvent at room temperature or insoluble in the hot solvent. The solvent should not react with the compound being purified. The solvent should be volatile enough to be easily removed from the solvent after the compound has crystallized.

The Synthesis
aniline + acetic anhydride acetanilide + acetic acid
O R N I C C H E M I S T Y

The Mechanism (Nacylation)

Nucleophilic aromatic substitution

- involves addition-elimination
O R G A N I C C H E M I S T R Y

Recrystallization: Purificationway of Rapid and convenient method


purifying a solid organic compound The material to be purified is dissolved in the hot appropriate solvent As the solvent cools, the solution become saturated with respect to the substance, which then crystallize Impurities stay in solution
O R G A N I C C H E M I S T R Y

Assessment of Result
Examine the following:
Physical appearance physical state, color, odor, texture, etc. Melting point determine the melting point range Percent yield calculate the yield of the reaction based on the experimental result and stoichiometry of the reaction Infrared spectra identify the functional groups present Oin the spectra and compare C C I R G A N the H E M spectrum with the obtained I S T R Y

Assessment of Result
Physical appearance
physical state: ________________

color: _____________ odor: _____________ texture: ___________


R G A N I C C H E M I S T R Y

Assessment of Result
Melting point
the melting point of a compound is a criterion for purity as well as for identification. pure, nonionic, crystalline organic compound usually has a sharp and narrow melting point range. very small amounts of miscible impurities will produce a depression of the melting point and an increase in the melting point range.

Assessment of Result
Percent yield
aniline + acetic anhydride acetanilide + acetic acid

Experimental yield: determine experimentally Theoretical yield: calculated from the limiting reagent Percent yield:

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