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Orgo 2213 Topic 10b Notes.docx

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Chemistry 1027A/B
Mel Usselman

Key Concepts In Organic Chemistry: Derivatives Of Carboxylic Acids (Usselman Version) -All carboxylic derivatives are formed from a substitution reaction of a carboxylic acid. All carboxylic acid derivatives have the acyl group in common. -For esters, change the “-ic acid” to “ate,” preceded by the name of the alkyl group on the ester OR group. Cyclic esters are called lactones and are designated σ, β, ϒ, δ, or ε depending on the number of carbon atoms the ester O atom is from the C =O. Esters are used frequently in phosphoric acid as they can make more ester bonds than carbon (mono-, di- or triphosphate esters). More variety is present with phosphoric acid as opposed to carboxylic acids. -For acid halides, change the “-ic acid” to “-yl halide.” For symmetrical anhydrides change “acid” to “anhydride.” Anhydrides are formed by coupling two carboxylic acids with the loss of water and cyclic anhydrides are easily formed by heating dicarboxylic acids (intramolecular reaction). -For amides, change “-oic acid” or “-ic acid” to “amide.” If the N of the amide group bears groups other than H, designate their attachment to the nitrogen by using the prefix “N” for each group. Amide bonds that like α-amino acids together is known as a peptide bond. Cyclic amides are called lactams, and when 3 two acyl groups form amide bonds to the same N atom an imide results. *Remember that no sp carbons can ever enter into resonance stabilization (no electron pairs). Lactams = cyclic amides, while lactones = cyclic esters. -1 -All acid derivatives contain a strong C = O stretch in the normal 1630-1800cm region. -*Acid chlorines are the most reactive of the acid derivatives and esters, anhydrides and amides are usually made from acid chlorides. -Acid derivatives can be interconverted one to another, and all can be converted to the parent carboxylic acid by nucleophilic acyl substitution. This mechanism involves the addition of a Nu to the C=O, followed by an elimination of the acyl substituent Y (acting as a LG). The mechanism of other acid- catalyzed nucleophilic acyl substitution reactions differs from this general mechanism only in the nature of the Nu. -When writing mechanisms for all chemical reactions, anions (but not cations) are the allowed species in basic conditions and cations (but not anions) are the allowed species in acidic conditions (base = anions only; acid = cations only). -All acid
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