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If You Want to Make a Carbon-Carbon Bond… (To the tune of “The Ants Go Marching”) By Hannah Korte, Amy Joiner, Britteny Johnson If you want to make a carbon carbon bond, a bond Of organic chem. you must be awfully fond, quite fond You might want to use SN2, or Friedel Crafts could work for you Don’t forget Organometallic and Diels-Alder , and Wittig, and condensation, and substitution…of carbonyl compounds Why don’t we tell you more? SN2 You start out with a nucleophile that’s strong, that’s strong With a primary alkyl halide it won’t be long, be long You’ll have a carbon carbon chain The number of nucleophiles you can use is insane, Such as alkyne salts, and cyanide, and thiol salts, and hydroxide and ethoxides, etcetera… Friedel Crafts For Friedel Crafts you never should forget, forget Strongly deactivating groups are a bad bet, bad bet You’ll need a catalyst like ferric bromide Or AlCl3 with alkyl halide for alkylation , but it rearranges So acylate with an acid chloride Organometallic Organolithium and Grignard are just alike, alike Except that carboxylic acids just don’t like, don’t like To form to ketones when Grignard is there And cuprates will make ketones even where The other reactions, can’t be stopped And they can be phenyl, alkenyl, primary, secondary, tertiary Diels-Alder If you want a cyclohexene on your first trial, first trial Put electron-donating groups on your dienophile, dienophile You don’t want those on your diene, though And keep in mind that the product’s endo You can even make bicyclic rings or cyclohexane Or particular sterioisomers…yeah BUM BUM BUM Wittig You first will need triphenylphosphine, phosphine This reaction’s meant to make a rare alkene, alkene Add triphenylphosphine to an alkyl halide Then NaNH2 for a resonance stabilized Ylide, which reacts, with carbonyls, to make A new double bond, right where you want it Carbonyl Alpha Hydrogens Pull off an alpha hydrogen with a base, a base It makes an enolate, but just a trace, a trace This type of reaction can readily be seen In aldol dehydration to make an alkene And other reactions include Claisen Condensation malonic alkylation, Michael addition, Robinson annulation And the Stork enamine reaction (There’s a bunch of them) If you want to make a carbon carbon bond, a bond Of organic chem. you must be awfully fond, quite fond— We’re done!
