Carboxylic acidsSlide 2Carboxylic AcidsSlide 4ReactionsSlide 6EstersSlide 8Slide 9AminesSlide 11Slide 12Slide 13AmidesCarboxylic acids1o alcohol aldehyde carboxylic acid[O][O]methanol methanal methanoic acid-+H-bond acceptorH-bond donorvery high b.p.2 H-bonds / molecule-Carboxylic acidsoic acid1234butan2-ethyloic acid123456hexan2-ethyl- 4-hydroxy2-ethyl4-hydroxyadd [O]oic acidhexan2-ethyl- 4-oxoCH3 – CH2 – CH – CH2 – CH – CO2HOHCH2 – CH3OCH3 – CH2 – CH – C CH2 – CH3OOHCarboxylic Acids+H++H+-resonance structureanion stabilizedChemical propertiesoctanoic acid+ NaOHNa++ H2Osodium octanoate + waterOO-OO-OO-OO-OO-OOOO-OO-OO-OO-OO-OOOOOO-OHOinsoluble in H2OsolubleH-bondingLDFiondipoleCarboxylic Acidsshort chain acids solubleH-bondingReactionsReduction:123456hexanoic acid5-oxoLiAlH4hexanediol1,5-H2/ PtNaBH4hexanoic acid5-hydroxyCH3C CH2CH2CH2COOHOCH3CH CH2CH2CH2 CH2OHOHCH3C CH2CH2CH2COOHOCH3CHCH2CH2CH2COHOHOReactionsnucleophilic substitutioncarboxylic acid+alcoholH++ H2Oestercondensation reactionreverse = hydrolysisester + H2OH+carboxylic acid+alcoholRCOOHHORRCOOREstersfrom acidfrom alcoholname = alkyl group from alcohol (yl)acid name changed to “oate”methylbutanoateapplepentylbutanoatepeachesRCOORCH3CH2CH2COO CH3CH3(CH2)2COO (CH2)4CH3EstersH-bond acceptorsOno H-bond donorlow b.p.dipole-dipole interactionswater solubleRCOOROCarboxylic acidsnucleophilic substitutioncarboxylic acid+amineheat+ H2Oamidecondensation reactioncarboxylic acid+ amineamide+ H2Ohydrolysis reactionamide+ H2Ocarboxylic acid+ amineR COOHNH RRNRRR CO..Aminesorganic analogs of ammoniaammonia 1o amine 2o amine 3o amineall have H-bond acceptor N-1o and 2o have H-bond donor H+high b.p.liquid at room Tgas at room Telectronegativity O N NHHHNHHRNHRRNRRRCH3OHNHHCH3 >Aminesnomenclature1. Name and alphabetize R groups and add “amine”methylamine1omethylamineethyl 2o3odimethylamineethyl low b.p.NHHCH3NH CH3CH2CH3NH3C CH3CH2CH3Amines+ H2O+ OH-Kb = [R-NH3+][OH-][R-NH2]smaller Kbweaker baseNRHHNHRHHweak basesAminesnucleophilic substitutionR COOHcarboxylic acidNH HR1o amineNHRR CO+H2Oamide2o amineNH RRNRRR CO+H2OamideNR RR3o amineno reaction+Condensation reactionheatAmidesC-Oand C-N double bond charactermolecule is flat and rigidno rotation about C-O or C-N bondsstructure of proteinsvery high b.p.NRRR CONRRR