By: Mica Blizzard Jeremy Nason Carboxylic Acids By: Mica Blizzard Jeremy Nason

Structure General Formula: O R-C-OH The carboxyl group is made up of a carbonyl (C=O) group and a hydroxyl (O-H) group

Nomenclature The substituent “–COOH” is called “carboxy” When naming carboxylic acids, you drop the “e” ending and add “oic acid” Ex: Hexanoic acid http://www.ivy-rose.co.uk/Chemistry/Organic/Naming-Carboxylic-Acids.php

Ex: cyclopentanecarboxylic acid In ring compounds when there is one or more “-COOH”, you just name it the way you would name a cycloalkane but you also add “carboxylic acid” Also note that the “–COOH” group is numbered one and the other substituents are numbered accordingly. Ex: cyclopentanecarboxylic acid http://www.chemsynthesis.com/base/chemical-structure-17568.html

When a metal replaces the hydrogen, you name the metal and then change the name of the acid to an “oate” ending Ex: sodium benzoate http://en.wikipedia.org/wiki/File:Sodium-benzoate-skeletal.png

Common Names Formic (Methanoic) acid: Acetic (Ethanoic) acid: Malonic (Propanedioic) acid: http://commons.wikimedia.org/wiki/File:Formic-acid-2D.png http://en.wikipedia.org/wiki/File:Acetic-acid-2D-flat.png http://www.xula.edu/chemistry/documents/orgleclab/sample.html

Propionic (Propoic) acid: Butyric (Butoic) acid: Benzoic (Butanedioic) acid: http://en.wikipedia.org/wiki/File:Propionic_acid_flat_structure.png http://en.wikipedia.org/wiki/File:Butyric_acid_flat_structure.png http://chemicaloftheday.squarespace.com/todays-chemical/2010/4/26/benzoic-acid.html

Properties Higher melting and boiling points than analogous alcohols Higher solubility in aqueous solution They are dimers in gas and dimers or aggregates in liquid.

Reactions Neutralization When the bond between oxygen and hydrogen breaks, the electron pair stays with the oxygen atom, giving it a negative charge. When you add water to a carboxylic acid, it neutralizes it. http://www.chemgapedia.de/vsengine/vlu/vsc/en/ch/12/oc/vlu_organik/c_acid/nomenklatur_und_strukt_carbons.vlu/Page/vsc/en/ch/12/oc/c_acid/s_b_cooh/s_b_cooh.vscml.html

A carboxylic acid and an alcohol form an ester and water. Ester Formation A carboxylic acid and an alcohol form an ester and water. http://catalog.flatworldknowledge.com/bookhub/reader/2547?e=gob-ch15_s08

When a carboxylic acid is in an organic solvent, it forms dimers. http://en.wikipedia.org/wiki/File:Carboxylic_acid_dimers.png

Video http://www.khanacademy.org/science/organic-chemistry/v/carboxylic-acid-naming