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    Grignard Reactions

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    Chris_Barber09
    Organic chemistry reactions involving R- and H- groups are discussed. R- groups such as RMgBr, RLi, and organocuprates act as strong nucleophiles that can attack carbonyls and epoxides to form new carbon-carbon bonds. NaH is used to deprotonate alcohols and other acidic O-H, N-H, or S-H groups, converting them to stronger nucleophiles/bases. Grignard reagents, alkyl lithiums, and organocuprates are synthesized from alkyl halides and can be used to add or replace functional groups or form new carbon-carbon bonds.

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    Grignard Reactions

    Uploaded by

    Chris_Barber09
    91 views2 pages
    Organic chemistry reactions involving R- and H- groups are discussed. R- groups such as RMgBr, RLi, and organocuprates act as strong nucleophiles that can attack carbonyls and epoxides to form new carbon-carbon bonds. NaH is used to deprotonate alcohols and other acidic O-H, N-H, or S-H groups, converting them to stronger nucleophiles/bases. Grignard reagents, alkyl lithiums, and organocuprates are synthesized from alkyl halides and can be used to add or replace functional groups or form new carbon-carbon bonds.

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    Grignard Reactions

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    Organic chemistry reactions involving R- and H- groups are discussed. R- groups such as RMgBr, RLi, and organocuprates act as strong nucleophiles that can attack carbonyls and epoxides to form new carbon-carbon bonds. NaH is used to deprotonate alcohols and other acidic O-H, N-H, or S-H groups, converting them to stronger nucleophiles/bases. Grignard reagents, alkyl lithiums, and organocuprates are synthesized from alkyl halides and can be used to add or replace functional groups or form new carbon-carbon bonds.

    Copyright:

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

    Grignard Reactions

    Uploaded by

    Chris_Barber09
    Organic chemistry reactions involving R- and H- groups are discussed. R- groups such as RMgBr, RLi, and organocuprates act as strong nucleophiles that can attack carbonyls and epoxides to form new carbon-carbon bonds. NaH is used to deprotonate alcohols and other acidic O-H, N-H, or S-H groups, converting them to stronger nucleophiles/bases. Grignard reagents, alkyl lithiums, and organocuprates are synthesized from alkyl halides and can be used to add or replace functional groups or form new carbon-carbon bonds.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 2

    organic chemistry: R- and Hoverview of reactions for R- and Has

    as bases
    nucleophiles
    (faster)
    attack carbonyls or epoxides
    RMgBr
    attack carbonyls or epoxides
    RLi
    attack carbonyls or epoxides
    LiAlH4
    attack carbonyls
    NaBH4
    NaH
    Another name for expoxides is oxacyclopropanes.

    deprotonate
    OH, NH,
    or SH

    acid-base reactions for R- and Hreactions:


    NaH + ROH
    HH + NaOR
    RMgX + ROH
    RH + ROMgX
    Similar deprotonation reactions with other O-H, N-H, or S-H groups.
    mechanisms:

    synthetic utility:
    NaH deprotonates alcohols, turning a poor nucleophile/base (neutral O, only good
    enough for SN1/E1) into a good nucleophile/base (O-, good enough for SN2/E2).
    To replace a functional group with a H:
    RMgX + H3O+
    RH + H2O + +MgX
    +
    Or, to replace a functional group with a D: RMgX + D3O
    RD + D2O + +MgX
    some other useful reactions
    to convert a 1 or 2 alcohol to an alkyl bromide:
    ROH + PBr3
    RBr
    to convert a 1 or 2 alcohol to an alkyl chloride:
    ROH + SOCl2
    RCl
    to convert a 3 alcohol to an alkyl halide:
    ROH + HX
    RX + H2O
    (SN1)
    (X=Cl, Br, or I)
    to synthesize a Grignard reagent: RX + Mg
    RMgX,
    X = Cl, Br, or I
    to synthesize an alkyl lithium:
    RX + 2 Li
    RLi + LiX
    to synthesize an organocuprate: 2 RLi + CuI
    R2CuLi + LiI
    Organocuprates can act as nucleophiles in an SN2 reaction: R2CuLi + RX
    R-R
    Grignards and alkyl lithiums, in contrast, cannot act as SN2 nucleophiles.
    Synthetic utility: Defunctionalizes, adds carbon-carbon sigma bonds.
    Some courses may not cover organocuprates.

    www.freelance-teacher.com

    organic chemistry: R- and Husing R- to attack carbonyls and epoxides


    reactions:

    synthetic utility:
    Form carbon-carbon bonds.
    RMgX + carbonyl forms a new C-C bond, with an O- on the C that was attacked.
    RMgX + epoxide forms a new C-C bond, with an O- on the C next to the C that was
    attacked.

    www.freelance-teacher.com

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