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    Synthesis of Acetanilide: Maria Salvacion A. Esmalla, M. SC

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    Ephraim Remann D. Garcia
    This document describes the synthesis and purification of acetanilide via recrystallization. It discusses choosing an appropriate recrystallization solvent based on solubility properties. Methanol is identified as the suitable solvent for purifying the synthesized acetanilide. The document outlines the recrystallization procedure and assessment of the purified product based on physical properties, melting point, percent yield, and infrared spectroscopy.

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    Synthesis of Acetanilide: Maria Salvacion A. Esmalla, M. SC

    Uploaded by

    Ephraim Remann D. Garcia
    377 views18 pages
    This document describes the synthesis and purification of acetanilide via recrystallization. It discusses choosing an appropriate recrystallization solvent based on solubility properties. Methanol is identified as the suitable solvent for purifying the synthesized acetanilide. The document outlines the recrystallization procedure and assessment of the purified product based on physical properties, melting point, percent yield, and infrared spectroscopy.

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    Acetanilide

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    This document describes the synthesis and purification of acetanilide via recrystallization. It discusses choosing an appropriate recrystallization solvent based on solubility properties. Methanol is identified as the suitable solvent for purifying the synthesized acetanilide. The document outlines the recrystallization procedure and assessment of the purified product based on physical properties, melting point, percent yield, and infrared spectroscopy.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPSX, PDF, TXT or read online from Scribd
    Download as ppsx, pdf, or txt
    377 views18 pages

    Synthesis of Acetanilide: Maria Salvacion A. Esmalla, M. SC

    Uploaded by

    Ephraim Remann D. Garcia
    This document describes the synthesis and purification of acetanilide via recrystallization. It discusses choosing an appropriate recrystallization solvent based on solubility properties. Methanol is identified as the suitable solvent for purifying the synthesized acetanilide. The document outlines the recrystallization procedure and assessment of the purified product based on physical properties, melting point, percent yield, and infrared spectroscopy.

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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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