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    03 - Beckmann Rearrangment - Chemistry

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    Jyothi Brothers
    The Beckmann rearrangement involves the rearrangement of oximes upon treatment with acid. The mechanism proceeds through protonation of the oxime hydroxyl group, followed by antimigration of an alkyl substituent across the nitrogen-oxygen double bond as this bond breaks. This results in formation of an amide while avoiding production of a free nitrene intermediate. The document provides an example mechanism and questions for students to test their understanding of the Beckmann rearrangement and related reactions.

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    03 - Beckmann Rearrangment - Chemistry

    Uploaded by

    Jyothi Brothers
    55 views5 pages
    The Beckmann rearrangement involves the rearrangement of oximes upon treatment with acid. The mechanism proceeds through protonation of the oxime hydroxyl group, followed by antimigration of an alkyl substituent across the nitrogen-oxygen double bond as this bond breaks. This results in formation of an amide while avoiding production of a free nitrene intermediate. The document provides an example mechanism and questions for students to test their understanding of the Beckmann rearrangement and related reactions.

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    03_Beckmann Rearrangment_Chemistry

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    The Beckmann rearrangement involves the rearrangement of oximes upon treatment with acid. The mechanism proceeds through protonation of the oxime hydroxyl group, followed by antimigration of an alkyl substituent across the nitrogen-oxygen double bond as this bond breaks. This results in formation of an amide while avoiding production of a free nitrene intermediate. The document provides an example mechanism and questions for students to test their understanding of the Beckmann rearrangement and related reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    55 views5 pages

    03 - Beckmann Rearrangment - Chemistry

    Uploaded by

    Jyothi Brothers
    The Beckmann rearrangement involves the rearrangement of oximes upon treatment with acid. The mechanism proceeds through protonation of the oxime hydroxyl group, followed by antimigration of an alkyl substituent across the nitrogen-oxygen double bond as this bond breaks. This results in formation of an amide while avoiding production of a free nitrene intermediate. The document provides an example mechanism and questions for students to test their understanding of the Beckmann rearrangement and related reactions.

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    REACTION OF THE DAY_03


    Chemistry

    Beckmann Rearrangment

    Mechanism :
    R1 R1 R2 – C = N – R1
    H+ +
    N N
    R2 O–H R2 O+– H O
    H H
    H
    (Antimigration)
    R2 – C – NH – R1 R2 – C = N – R1 R2 – C = N – R1
    Tautomerise –H+
    O O–H O
    +
    H H
    In this rearrangement selectively antigroup migration observed irrespective of the migrating aptitude of groups
    bonded to doubly bonded carbon atom.

    Oximes generally have a high barrier to inversion, and accordingly this reaction is envisioned to proceed by protona-
    tion of the oxime hydroxyl, followed by migration of the alkyl substituent "trans" to nitrogen. The N-O bond is
    simultaneously cleaved with the expulsion of water, so that formation of a free nitrene is avoided.

    (1)
    

    Try Yourself
    1. Which oximes on treatement with concentrated H2SO4 undergoe rearrangement to give single amide?

    N – OH N – OH
    (1) (2)

    (3) CH3 – CH = N – OH (4)

    2. In the reaction given below,

    expected product(s) is

    O
    O
    H
    N H
    (1) (2) N

    H
    H N
    N
    (3) (4)
    O
    O

    (2)
    3. What is X in the following reaction?

    (1) (2)

    (3) (4)

    4. What is the final major product in the following reaction?

    (1) (2)

    (3) (4)

    dil. H2SO4
    Product
    5.
    N
    OH

    Product formed in this reaction is

    (3)
    CN CN

    (1) (2)

    Me

    NC NC

    (3) (4)

    

    Answer of question based on Baeyer-Villiger Oxidation


    1. Answer (2)
    2. Answer (1)
    3. Answer (4)
    4. Answer (1)
    5. Answer (3)

    (4)

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