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!