BrCh17 - 17-17-1Carboxylic Carboxylic AcidsAcidsChapter...

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Unformatted text preview: 17-17-1Carboxylic Carboxylic AcidsAcidsChapter 17Chapter 1717-17-2◆The functional group of a carboxylic acid is a carboxyl group.•the general formula for an aliphatic carboxylic acid is RCOOH; that for an aromatic carboxylic acid is ArCOOH.17.1 17.1 StructureStructureCOOHCO2HOO HCOO HAlternative representations for a carboxyl group17-17-317.2 17.2 A.A.Nomenclature - IUPACNomenclature - IUPAC◆IUPAC names: drop the -eefrom the parent alkane and add the suffix -oic acid.oic acid.•if the compound contains a carbon-carbon double bond, change the infix -anan-to -enen-HCOOHCH3COOH3-Methylbutanoic acid(Isovaleric acid)Ethanoic acid(Acetic acid)Methanoic acid(Formic acid)OHOPropenoic acid(Acrylic acid)trans-3-Phenylpropenoic acid(Cinnamic acid)trans-2-Butenoic acid(Crotonic acid)OHOOHOOHO17-17-4Nomenclature - IUPACNomenclature - IUPAC◆The carboxyl group takes precedence over most other functional groups.5-Oxohexanoic acid4-Aminobutanoic acid(R)-5-HydroxyhexanoicacidOHOOHOOHOH2NOHO17-17-5Nomenclature - IUPACNomenclature - IUPAC•dicarboxylic acids: add the suffix -dioic aciddioic acidto the name of the parent alkane containing both carboxyl groups.HOOHOPropanedioic acid(Malonic acid)Ethanedioic acid(Oxalic acid)OHOOHOOHexanedioic acid(Adipic acid)Pentanedioic acid(Glutaric acid)Butanedioic acid(Succinic acid)OOHOHOOHOHOOHOOHOO17-17-6Nomenclature - IUPACNomenclature - IUPAC•if the carboxyl group is bonded to a ring, name the ring compound and add the suffix -carboxylic carboxylic acid.acid.•benzoic acid is an aromatic carboxylic acid•use numbers to show the location of substituents.COOHCOOHHOOC3212-Cyclohexenecarboxylicacidtrans-1,3-CyclopentanedicarboxylicacidCOOHCOOHOHCOOHCOOHCOOHCOOHBenzoicacid2-Hydroxybenzoic acid(Salicylic acid)1,2-Benzenedicarboxylic acid(Phthalic acid)1,4-Benzenedicarboxylic acid(Terephthalic acid)17-17-7B.B.Nomenclature-CommonNomenclature-Common•when common names are used, the letters α, β , γ , δ ,etc. are often used to locate substituents.L-alanine][(S)-α-Aminopropionic acid;(γ-Aminobutyric acid, GABA)(S)-2-Aminopropanoic acid4-Aminobutanoic acid4325H2NOHOOHONH2OHOαβγδ117-17-817.3 17.3 Physical PropertiesPhysical Properties◆In the liquid and solid states, carboxylic acids are associated by hydrogen bonding into dimeric structures.17-17-9Physical PropertiesPhysical Properties◆Carboxylic acids have significantly higher boiling points than other types of organic compounds of comparable molecular weight.•they are polar compounds and form very strong intermolecular hydrogen bonds.◆Carboxylic acids are more soluble in water than alcohols, ethers, aldehydes, and ketones of comparable molecular weight....
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This note was uploaded on 01/17/2011 for the course CHEM 109C taught by Professor Bruice during the Fall '08 term at UCSB.

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BrCh17 - 17-17-1Carboxylic Carboxylic AcidsAcidsChapter...

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