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Carboxylic Acids

Carboxylic acids have the highest priority, always named by adding -oic acid to the alkyl root.

Cyclic carboxylic acids are named as cycloalkanes carboxylic acids.  Salts of carboxylic acids are named with the cation, followed by the acid with the ending -oate.

Dicarboxylic acids are molecules with two carboxyl groups.  The first six straight-chain terminal dicarboxylic acids are:

Oxalic/ethanedioic acid (2C)

Malonic/propanedioic acid (3C)

Succinic/butanedioic acid (4C)

Glutaric/pentanedioic acid (5C)

Adipic/hexanedioic acid (6C)

Pimelic/heptanedioic acid (7C)

Carboxylic acids are polar and form hydrogen bonds with one another at two different points.  As a result, carboxylic acids form dimers.

Acidity of carboxylic acids is due to resonance stabilization of the carboxylate anion.

Electron-withdrawing groups, such as -Cl or -NO₂, as substituents on carbon atoms near the carboxyl group further absorb the negative charge and increase acidity.

Electron-donating groups, such as -NH₂ or -OCH₃, donate additional electron density and destabilize the negative charge, making the compound less acidic.

In dicarboxylic acids, one -COOH influences the other, making the compound more acidic than a monocarboxylic acid.  Once the proton leaves, and the carboxylate anion has formed, the second carboxyl group is less acidic.

Beta dicarboxylic acids have highly acidic α-hydrogens locate on the carbon between the two carboxyl groups.  Loss of this acidic hydrogen atom produces a carbanion that is stabilized by the electron-withdrawing effect of two carboxyl groups.

Carboxylic acids can be prepared via oxidation of aldehydes, primary alcohols and certain alkylbenzene.  The oxidant is usually potassium permanganate, KMnO₄.

Organometallic reagents, such as Grignard reagents, react with CO₂ to form carboxylic acids, and are useful for the conversion of tertiary alkyl halides.

The cyanide anion (-C≡N) carries the negative charge on the carbon atom, making it a great nucleophile but not a great base.

It will displace primary and secondary halides in SN2.  Nitriles can then be hydrolyzed under either acidic or basic conditions, producing carboxylic acids and ammonia.

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Use this comprehensive list to reference common compounds and ions conveniently.  I made this especially to give a lump sum of practice problems for drawing Lewis Structures.  Suggestions and comments appreciated, thanks!

Revised simpler edit (1/9/15) with elements sorted, and I changed everything to structural formula. 

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47th Street - New York - 1957 - photograph by André Robé

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let’s cuddle naked and see who gives in first

csurf (via hefuckin)

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Cry me a fucking river