organicchemistry.pptVIP

Organic Chemistry William H. Brown Christopher S. Foote Brent L. Iverson Arrhenius Acids and Bases In 1884, Svante Arrhenius proposed these definitions acid: a substance that produces H3O+ ions aqueous solution base: a substance that produces OH- ions in aqueous solution this definition of an acid is a slight modification of the original Arrhenius definition, which was that an acid produces H+ in aqueous solution today we know that H+ reacts immediately with a water molecule to give a hydronium ion Br?nsted-Lowry Definitions Acid: a proton donor Base: a proton acceptor Conjugate Acids Bases conjugate base: the species formed from an acid when it donates a proton to a base conjugate acid: the species formed from a base when it accepts a proton from an acid acid-base reaction: a proton-transfer reaction conjugate acid-base pair: any pair of molecules or ions that can be interconverted by transfer of a proton Conjugate Acids Bases Br?nsted-Lowry definitions do not require water as a reactant consider the following reaction between acetic acid and ammonia Conjugate Acids Bases we can use curved arrows to show the flow of electrons in an acid-base reaction Conjugate Acids Bases Many organic molecules have two or more sites that can act as proton acceptors in this chapter, we limit our discussion to carboxylic acids, esters, and amides in these molecules, the favored site of protonation is the one in which the charge is more delocalized question: which oxygen of a carboxylic acid is protonated? Conjugate Acids Bases for protonation on the carbonyl oxygen, we can write three contributing structures two place the positive charge on oxygen, one places it on carbon A-1 and A-3 make the greater contribution because all atoms have complete octets the positive charge is delocalized over three atoms with the greater share on the two equivalent oxygens Conjugate Acids Bases for protonation on the hydroxyl oxygen, we can write two contributing structures B-2 makes