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    (2R) 2 Chloro 2 Methylbutan 1 Ol

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    Yash Shinde
    The document discusses ring-opening reactions of epoxides. It explains that epoxides undergo SN2 reactions when the ring is opened. For four examples (a through d), it shows the step-wise mechanisms for ring opening reactions of different epoxides. In each case, the epoxide is protonated to form an intermediate, which then undergoes nucleophilic attack by a chloride, bromide, or hydroxide ion on the more substituted carbon. It identifies the specific product formed in each reaction.

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    (2R) 2 Chloro 2 Methylbutan 1 Ol

    Uploaded by

    Yash Shinde
    98 views2 pages
    The document discusses ring-opening reactions of epoxides. It explains that epoxides undergo SN2 reactions when the ring is opened. For four examples (a through d), it shows the step-wise mechanisms for ring opening reactions of different epoxides. In each case, the epoxide is protonated to form an intermediate, which then undergoes nucleophilic attack by a chloride, bromide, or hydroxide ion on the more substituted carbon. It identifies the specific product formed in each reaction.

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    Original Title

    597706-18-28E

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    The document discusses ring-opening reactions of epoxides. It explains that epoxides undergo SN2 reactions when the ring is opened. For four examples (a through d), it shows the step-wise mechanisms for ring opening reactions of different epoxides. In each case, the epoxide is protonated to form an intermediate, which then undergoes nucleophilic attack by a chloride, bromide, or hydroxide ion on the more substituted carbon. It identifies the specific product formed in each reaction.

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    98 views2 pages

    (2R) 2 Chloro 2 Methylbutan 1 Ol

    Uploaded by

    Yash Shinde
    The document discusses ring-opening reactions of epoxides. It explains that epoxides undergo SN2 reactions when the ring is opened. For four examples (a through d), it shows the step-wise mechanisms for ring opening reactions of different epoxides. In each case, the epoxide is protonated to form an intermediate, which then undergoes nucleophilic attack by a chloride, bromide, or hydroxide ion on the more substituted carbon. It identifies the specific product formed in each reaction.

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    © All Rights Reserved
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    597706-18-28E AID: 987 | 17/11/2015

    RID: 700 | 22/12/2015


    AID: 1112 |4/07/2017

    Epoxides have a lot of ring strain which makes them much more reactive that acyclic
    ethers. Ring opening of epoxides is an SN2 reaction.

    (a)

    Ring cleavage occurs via following steps:

    Protonation of the epoxide to form an intermediate:

    +
    H
    H
    O O
    +
    H CH 2CH 3
    H CH 2CH 3

    H CH3
    H CH3

    The protonated epoxide now undergoes a back-side attack of the chloride ion on more
    substituted carbon atom and forms the corresponding product.

    H
    +
    O H O
    H CH 2CH 3 H CH 2CH 3

    H CH3 H CH3
    - Cl
    Cl
    (2R)-2-chloro-2-methylbutan-1-ol

    Therefore, the product formed is (2R)-2-chloro-2-methylbutan-1-ol.

    (b)

    Ring cleavage occurs via following steps:

    Protonation of the epoxide to form an intermediate:

    +
    H +
    O O H

    CH3 CH3

    The protonated epoxide now undergoes a back-side attack of the bromide ion on more
    substituted carbon atom and forms the corresponding product.

    OH
    +
    O H
    CH3
    CH3
    Br
    -
    Br (1S,2S)-2-bromo-2-methylcyclohexan-1-ol

    Therefore, the product formed is (1S,2S)-2-bromo-2-methylcyclohexan-1-ol.

    (c)

    Ring cleavage occurs via following steps:

    Protonation of the epoxide to form an intermediate:

    The protonated epoxide undergoes now a back-side attack of the water molecule on more
    substituted carbon atom and forms the corresponding product.
    H
    +
    O
    H HO
    H
    CH3
    CH3 +
    H2O O
    H H

    O H
    H

    CH3
    O H

    Therefore, the product formed is 1-[(1S)-1-hydroxyethyl]cyclohexan-1-ol.

    (d)

    Ring cleavage occurs via following steps:

    Protonation of the epoxide to form an intermediate:

    +
    H +
    O OH

    CH 2CH 3 CH 2CH 3

    The protonated epoxide undergoes back side attack of the chloride ion on more
    substituted carbon atom and forms the corresponding product.

    H
    O H

    +
    HO
    Cl

    CH 2CH 3 CH 2CH 3
    -
    Cl
    (1S,2S)-2-chloro-2-ethylcyclohexan-1-ol

    Therefore, the product formed is (1S,2S)-2-chloro-2-ethylcyclohexan-1-ol.

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