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    This document describes the Williamson synthesis of ethers. It involves the nucleophilic substitution reaction between an alkoxide ion and a good SN2 substrate. The alkoxide ion is usually formed from the alcohol with the more hindered group. This displaces the leaving group, typically a halide or tosylate, of the other reactant. An example reaction is given to synthesize cyclopentyl ethyl ether. The document also provides a practice problem testing understanding of the Etard reaction to form an ether.

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    13. Williamson Synthesis of Ethers (1)

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    This document describes the Williamson synthesis of ethers. It involves the nucleophilic substitution reaction between an alkoxide ion and a good SN2 substrate. The alkoxide ion is usually formed from the alcohol with the more hindered group. This displaces the leaving group, typically a halide or tosylate, of the other reactant. An example reaction is given to synthesize cyclopentyl ethyl ether. The document also provides a practice problem testing understanding of the Etard reaction to form an ether.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    1 views3 pages

    Williamson Synthesis of Ethers

    Uploaded by

    khatripk2812
    This document describes the Williamson synthesis of ethers. It involves the nucleophilic substitution reaction between an alkoxide ion and a good SN2 substrate. The alkoxide ion is usually formed from the alcohol with the more hindered group. This displaces the leaving group, typically a halide or tosylate, of the other reactant. An example reaction is given to synthesize cyclopentyl ethyl ether. The document also provides a practice problem testing understanding of the Etard reaction to form an ether.

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

    Date- 11-11-2023

    Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Ph.: 011-47623456

    MOLECULE MAGIC
    Chemistry
    Williamson Synthesis of Ethers

    This method is suitable for the preparation of a wide variety of unsymmetric ethers.
    Mechanism of the Williamson Synthesis
    Step 1 : Formation of the alkoxide of the alcohol having the more hindered group.

    Step 2 : The alkoxide ion displaces the leaving group of a good SN2 substrate.

    Example : Synthesis of cyclopentyl ethyl ether


    Step 1 : Form the alkoxideion of the alcohol with the more hindered group.

    Step 2 : The alkoxide ion displaces the leaving group of a good SN2 substrate.

    In proposing a Williamson synthesis, we usually choose the less hindered alkyl group to be the halide (or
    tosylate) and the more hindered group to be the alkoxide ion.
    If the substrate is tertiary, elimination is the exclusive result .

    

    (1)
    Try Yourself

    OH
    (i) KOH(excess)
    HO O (ii)Ph–CH2–Cl (excess)
    1. HO
    dioxane
    OH
    Product obtained in above reaction is

    CH2Ph
    HO O
    (1) HO

    OH

    CH2Ph
    PhCH2
    O
    (2) PhCH2
    CH2Ph

    OCH2Ph
    PhCH2O O
    (3) PhCH2O
    OCH2Ph

    OCH2Ph
    HO O
    (4) HO
    OCH2Ph

    Answer of Question Based on Etard Reaction


    1. Answer (1)

    

    (2)

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