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    05 Rohan Bhilkar POAC LAB 05

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    Rohan Bhilkar
    The document describes the synthesis of p-nitro acetanilide from acetanilide. Acetanilide is treated with a nitrating mixture of nitric acid and sulfuric acid, which results in an electrophilic substitution reaction forming p-nitro acetanilide as the major product. The p-nitro acetanilide crystals are isolated through crystallization in ethyl alcohol and have a melting point of 214°C. The reaction is carried out at a temperature below 20°C and yields the expected product amount of 4g of colorless p-nitro acetanilide crystals.

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    05 Rohan Bhilkar POAC LAB 05

    Uploaded by

    Rohan Bhilkar
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    The document describes the synthesis of p-nitro acetanilide from acetanilide. Acetanilide is treated with a nitrating mixture of nitric acid and sulfuric acid, which results in an electrophilic substitution reaction forming p-nitro acetanilide as the major product. The p-nitro acetanilide crystals are isolated through crystallization in ethyl alcohol and have a melting point of 214°C. The reaction is carried out at a temperature below 20°C and yields the expected product amount of 4g of colorless p-nitro acetanilide crystals.

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    05_Rohan_Bhilkar_POAC_LAB_05

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    The document describes the synthesis of p-nitro acetanilide from acetanilide. Acetanilide is treated with a nitrating mixture of nitric acid and sulfuric acid, which results in an electrophilic substitution reaction forming p-nitro acetanilide as the major product. The p-nitro acetanilide crystals are isolated through crystallization in ethyl alcohol and have a melting point of 214°C. The reaction is carried out at a temperature below 20°C and yields the expected product amount of 4g of colorless p-nitro acetanilide crystals.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    14 views3 pages

    05 Rohan Bhilkar POAC LAB 05

    Uploaded by

    Rohan Bhilkar
    The document describes the synthesis of p-nitro acetanilide from acetanilide. Acetanilide is treated with a nitrating mixture of nitric acid and sulfuric acid, which results in an electrophilic substitution reaction forming p-nitro acetanilide as the major product. The p-nitro acetanilide crystals are isolated through crystallization in ethyl alcohol and have a melting point of 214°C. The reaction is carried out at a temperature below 20°C and yields the expected product amount of 4g of colorless p-nitro acetanilide crystals.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 3

    VISHVAKARMA INSTITUE OF TECHNOLOGY,

    PUNE-411046

    PHYSICAL AND ORGANIC CHEMISTRY


    Lab 05: Synthesis of P-Nitro Acetanilide from acetanilide
    Name: Rohan R. Bhilkar Division B
    Roll No: 05 GR No. 12120205

    Aim:
    To prepare p-Nitro acetanilide from acetanilide and acetic acid in the presence of nitrating
    mixture.

    Theory:
    The organic compound p-nitro acetanilide is prepared from acetanilide through nitration.
    When acetanilide is treated with a nitrating mixture that is a mixture of nitric acid and
    sulphuric acid p-nitro acetanilide is formed. Along with p-nitroacetanilide, o-nitroacetanilide
    is also formed as a minor product. Since o-nitro acetanilide is very much soluble in alcohol it
    is very easy to isolate p-nitro acetanilide through crystallization.
    The chemical reactions involved in this process are given below.

    It is an electrophilic substitution reaction. The electrophile -NO2 will attach the para position
    because the -NHCOCH3 is an electron releasing group. Nitro anilines can be prepared by this
    type of reaction because nitration of aniline is not possible, the amino group gets oxidized
    with the nitrating mixture. In order to protect the amino group from oxidation, acetanilide is
    first nitrated to give p-nitro acetanilide and then on hydrolysis to give p-nitroaniline which is
    difficult to obtain by direct nitration.
    Other names – N-(4-nitrophenyl) acetamide, p-Acetamidonitrobenzene, p-Nitroacetanilide,
    N-Acetyl-4-nitroaniline

    Materials Required:

    • Acetanilide
    • Acetic acid
    • Concentrated Sulphuric acid
    • Fuming Nitric acid
    • Ethyl alcohol
    • Conical flask
    • Beaker
    • Dropping funnel
    • Filter paper
    • Glass rod
    • Buchner funnel
    • Pipette

    Apparatus Setup:
    Procedure:

    • Take 3gm of finely powdered acetanilide in a clean beaker and dissolve it by adding
    glacial acetic acid by stirring the content carefully at room temperature.
    • Gently warm the mixture to dissolve acetanilide completely.
    • Cool the solution and add concentrated sulphuric acid slowly with constant stirring.
    The solution becomes warm, keep the mixture in ice-bath and clear solution is
    obtained.
    • To the cool solution add fuming nitric acid dropwise through a dropping funnel with
    constant stirring.
    • Maintain the temperature below 20oC during the whole process.
    • Once the addition of nitric acid is completed, the beaker is removed from the freezing
    mixture bath and allow standing for half an hour at room temperature.
    • Pour the mixture into 100gm of crushed ice in a beaker and stir well.
    • Large crystals of p-nitroacetanilide is obtained. Filter the crystals through filter paper.
    • The separated p-nitroacetanilide is washed with cold water in order to remove excess
    of acid.
    • It is crystallized from ethyl alcohol. Dry the crystals in the folds of filter paper and
    weigh them to know the yield.

    Observations:

    Colour of the crystals Colourless

    Melting point 214oC

    Expected yield 4gm

    Results and Discussion:


    The yield of p-Nitro acetanilide is 4gm.

    Precautions:

    1. Temperature should not exceed more than 20oC.


    2. Advisable to add nitric acid into the reaction mixture while it is immersed in ice-bath
    3. Add fuming nitric acid drop by drop carefully and do not inhale the fumes of nitric
    acid.

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