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    Adisi Elektrofilik Kimia Organik

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    Acika
    1) The document discusses addition reactions of electrophilic species such as Cl2, Br2, HOCl, and HOBr to conjugated alkenes. It describes the formation of a bridged halonium ion intermediate and the anti-addition of the halide ion to give the final product. 2) The addition of HOCl and HOBr to alkenes forms halohydrins, which contain an -OH group and halogen atom on adjacent carbons. This involves formation of a bridged halonium ion intermediate followed by attack of water and proton transfer. 3) Hydroboration of alkenes with BH3 is discussed, forming trialkylbor

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    Adisi Elektrofilik Kimia Organik

    Uploaded by

    Acika
    64 views25 pages
    1) The document discusses addition reactions of electrophilic species such as Cl2, Br2, HOCl, and HOBr to conjugated alkenes. It describes the formation of a bridged halonium ion intermediate and the anti-addition of the halide ion to give the final product. 2) The addition of HOCl and HOBr to alkenes forms halohydrins, which contain an -OH group and halogen atom on adjacent carbons. This involves formation of a bridged halonium ion intermediate followed by attack of water and proton transfer. 3) Hydroboration of alkenes with BH3 is discussed, forming trialkylbor

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    1) The document discusses addition reactions of electrophilic species such as Cl2, Br2, HOCl, and HOBr to conjugated alkenes. It describes the formation of a bridged halonium ion intermediate and the anti-addition of the halide ion to give the final product. 2) The addition of HOCl and HOBr to alkenes forms halohydrins, which contain an -OH group and halogen atom on adjacent carbons. This involves formation of a bridged halonium ion intermediate followed by attack of water and proton transfer. 3) Hydroboration of alkenes with BH3 is discussed, forming trialkylbor

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    64 views25 pages

    Adisi Elektrofilik Kimia Organik

    Uploaded by

    Acika
    1) The document discusses addition reactions of electrophilic species such as Cl2, Br2, HOCl, and HOBr to conjugated alkenes. It describes the formation of a bridged halonium ion intermediate and the anti-addition of the halide ion to give the final product. 2) The addition of HOCl and HOBr to alkenes forms halohydrins, which contain an -OH group and halogen atom on adjacent carbons. This involves formation of a bridged halonium ion intermediate followed by attack of water and proton transfer. 3) Hydroboration of alkenes with BH3 is discussed, forming trialkylbor

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    ADISI ELEKTOFILIK

    Adisi 1,2 Dan 1,4 Alkena Terkonjugasi

    • Contoh
    Mekanisme reaksi
    Addition of Cl2 and Br2
    – Step 1: formation of a bridged bromonium ion
    intermediate
    Br
    Br
    Br Br Br
    -
    C C C C C C C C + Br

    These carbocations are major The bridged bromonium


    contributing structures ion retains the geometry
    – Step 2: attack of halide ion (a nucleophile) from the
    opposite side of the bromonium ion (an electrophile)
    opens the three-membered ring to give the product

    Br Br
    Br
    C C C C
    Br
    - Br
    Br
    Anti (coplanar) orientation Newman projection
    of added bromine atoms of the product
    Br
    Br Br

    C C C C
    Br
    - Br
    Br Anti (coplanar) orientation Newman projection
    of added bromine atoms of the product
    Addition of HOCl and HOBr
    • Treatment of an alkene with Br2 or Cl2 in water
    forms a halohydrin
    • Halohydrin: a compound containing -OH and -X
    on adjacent carbons
    HO Cl
    CH3 CH=CH2 + Cl2 + H2 O CH3 CH-CH2 + HCl
    Propene 1-Chloro-2-propanol
    (a chlorohydrin)
    Addition of HOCl and HOBr
    Step 1: formation of a bridged halonium ion intermediate

    :
    : Br :
    : Br :

    :
    : Br : : Br :
    :

    -
    H H - Br
    C C C C C C
    R H H H H H
    R H R H
    bridged bromonium minor contributing
    ion structure
    Step 2: attack of H2O on the more substituted carbon opens the
    three-membered ring
    : Br : H

    :
    : Br :
    R
    C C C C
    H H
    :

    H O: R + H
    H O H
    H H H
    :
    Addition of HOCl and HOBr
    – Step 3: proton transfer to H2O completes the reaction

    H Br H Br
    R R
    C C C C + H3 O +
    + H H
    O O
    H • •
    H H H • • H
    O H
    H
    Hydroboration/Oxidation
    Hydroboration: the addition of borane, BH3, to an alkene
    to form a trialkylborane
    H CH 2 CH 3
    H B + 3 CH 2 =CH 2 CH 3 CH 2 B
    H CH 2 CH 3
    Borane Triethylborane
    (a trialkylborane)
    Reaksi Diels-Alder

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