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    Carbon-Carbon Bond Forming Reactions: R' R X R R'

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    Julia Maramat
    This document describes several carbon-carbon bond forming reactions: 1) S N 2 displacement with cyanide extends a carbon chain by one carbon, 2) addition of acetylide performs alkylation, 3) nucleophilic addition of organometallic reagents directly adds to carbonyls, esters, and epoxides, 4) alkylation occurs through base-catalyzed reactions or alkyl halides, 5) condensation reactions include aldol and Claisen condensations to form carbon-carbon bonds, 6) Friedel-Crafts reactions perform alkylation and acylation, 7) the Wittig reaction converts a carbonyl to an alkene in a cis-selective manner, and 8)

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    Carbon-Carbon Bond Forming Reactions: R' R X R R'

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    Julia Maramat
    19 views2 pages
    This document describes several carbon-carbon bond forming reactions: 1) S N 2 displacement with cyanide extends a carbon chain by one carbon, 2) addition of acetylide performs alkylation, 3) nucleophilic addition of organometallic reagents directly adds to carbonyls, esters, and epoxides, 4) alkylation occurs through base-catalyzed reactions or alkyl halides, 5) condensation reactions include aldol and Claisen condensations to form carbon-carbon bonds, 6) Friedel-Crafts reactions perform alkylation and acylation, 7) the Wittig reaction converts a carbonyl to an alkene in a cis-selective manner, and 8)

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    This document describes several carbon-carbon bond forming reactions: 1) S N 2 displacement with cyanide extends a carbon chain by one carbon, 2) addition of acetylide performs alkylation, 3) nucleophilic addition of organometallic reagents directly adds to carbonyls, esters, and epoxides, 4) alkylation occurs through base-catalyzed reactions or alkyl halides, 5) condensation reactions include aldol and Claisen condensations to form carbon-carbon bonds, 6) Friedel-Crafts reactions perform alkylation and acylation, 7) the Wittig reaction converts a carbonyl to an alkene in a cis-selective manner, and 8)

    Copyright:

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    Download as PDF, TXT or read online from Scribd
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    Download as pdf or txt
    19 views2 pages

    Carbon-Carbon Bond Forming Reactions: R' R X R R'

    Uploaded by

    Julia Maramat
    This document describes several carbon-carbon bond forming reactions: 1) S N 2 displacement with cyanide extends a carbon chain by one carbon, 2) addition of acetylide performs alkylation, 3) nucleophilic addition of organometallic reagents directly adds to carbonyls, esters, and epoxides, 4) alkylation occurs through base-catalyzed reactions or alkyl halides, 5) condensation reactions include aldol and Claisen condensations to form carbon-carbon bonds, 6) Friedel-Crafts reactions perform alkylation and acylation, 7) the Wittig reaction converts a carbonyl to an alkene in a cis-selective manner, and 8)

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    of 2

    Carbon-Carbon Bond Forming Reactions

    1. S N 2 Displacement with Cyanide

    KCN R X R CN

    one carbon chain extension

    2. Addition of Acetylide

    R'

    R R'

    alkylation

    O R' R R'

    OH R' R R'
    nucleophile addition to carbonyls

    3. Nucleophilic Addition of Organometallic Reagents a. direct addition

    R'MgX or R'Li

    OH R'

    to aldehydes & ketones

    O OR

    R'MgX or R'Li

    OH R' R' OH R R'

    to esters

    O R

    R'MgX, CuI or R'2CuLi

    to epoxides

    b. conjugate addition

    R'2CuLi

    O R'

    4. Alkylation

    O 1. base 2. R'X

    O R'

    5. Condensation

    O R H

    OH O NaOR ROH R R H or R R

    O H

    aldol / mixed aldol (aldehydes & ketones)

    O R OMe

    O NaOMe MeOH R R

    O OMe

    Claisen condensation (esters or ester/ketone)

    6. Friedel-Crafts Reactions

    R3CCl AlCl3

    CR3

    alkylation

    O R Cl AlCl3

    O R
    acylation

    7. W ittig Reaction

    O R H

    Ph3P=CHR' R

    H H R'
    cis selective (some exceptions)

    8. Diels-Alder reaction

    CO2Me CO2Me

    or Lewis acid

    CO2Me
    endo TS favored

    CO2Me

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