节醛酮光谱分析红外中基团存在显而易见columbia有机化学课件17 html1.pptx

Section17.17

SpectroscopicAnalysisof

AldehydesandKetones

PresenceofaC=Ogroupisreadilyapparent

ininfraredspectrumC=Ostretchinggivesanintenseabsorption

at1710-1750cm-1InadditiontopeakforC=O,aldehydesgive

twoweakpeaksnear2720and2820nm

forH—C=OInfraredSpectroscopy

FrancisA.Carey,OrganicChemistry,FourthEdition.Copyright?2000TheMcGraw-HillCompanies,Inc.Allrightsreserved.200035003000250010001500500Wavenumber,cm-1Figure17.13InfraredSpectrumofButanalC=OCH3CH2CH2CH=OH—C=O

Aldehydes:H—C=Oprotonisatverylowfield

(d9-10ppm).Methylketones:CH3singletneard2ppm.1HNMR

01.02.03.04.05.06.07.08.09.010.0Chemicalshift(d,ppm)Figure17.14HCOCH(CH3)2

01.02.03.04.05.06.07.08.09.010.0Chemicalshift(d,ppm)Figure17.15CH3COCH3CH2

13CNMR Carbonylcarbonisatextremelylowfield-neard200ppm Intensityofcarbonylcarbonisusuallyweak

Chemicalshift(d,ppm)Figure17.16020406080100120140160180200CH3CH2CCH2CH2CH2CH3O

UV-VIS AldehydesandketoneshavetwobandsintheUVregion:

p?p*andn?p* p?p*:excitationofabondingpelectrontoanantibondingp*orbital p?p*:excitationofanonbondingelectrononoxygentoanantibondingp*orbital

UV-VISH3CH3CCO???

?p?p*lmax187nmn?p*lmax270nm

Molecularionfragmentstogiveanacylcationm/z86+m/z57MassSpectrometryCH2CH3?CH3CH2CCH2CH3?+O?

?CH3CH2CO?

?+