Chapter18

Chapter18 - 18-18-1Aldehydes Aldehydes&& 18Chapter...

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Unformatted text preview: 18-18-1Aldehydes Aldehydes & & KetonesKetonesChapter 18Chapter 1818-18-2The Carbonyl GroupThe Carbonyl Group◆In this and several following chapters, we study the physical and chemical properties of classes of compounds containing the carbonyl group, C=O•aldehydes and ketones (Chapter 18)•carboxylic acids (Chapter 20)•acid halides, acid anhydrides, esters, amides (Chapter 21)•enolate anions (Chapter 22)18-18-3The Carbonyl GroupThe Carbonyl Group•the carbonyl group consists of one sigma bond formed by the overlap of sp2hybrid orbitals and one pi bond formed by the overlap of parallel 2porbitals•pi bonding and pi antibonding MOs for formaldehyde18-18-4StructureStructure•the functional group of an aldehyde is a carbonyl group bonded to a H atom and a carbon atom •the functional group of a ketone is a carbonyl group bonded to two carbon atomsPropanone(Acetone)Ethanal(Acetaldehyde)Methanal(Formaldehyde)OOOCH3CHHCHCH3CCH318-18-5NomenclatureNomenclature◆IUPAC names:•the parent chain is the longest chain that contains the functional group•for an aldehyde, change the suffix from -e-eto -al-al•for an unsaturated aldehyde, change the infix from -an--an-to -en--en-; the location of the suffix determines the numbering pattern•for a cyclic molecule in which -CHO is bonded to the ring, add the suffix -carbaldehydecarbaldehyde18-18-6Nomenclature: AldehydesNomenclature: Aldehydes•the IUPAC retains the common names benzaldehyde and cinnamaldehyde, as well formaldehyde and acetaldehydeHO3-Methylbutanal2-Propenal(Acrolein)(2E)-3,7-Dimethyl-2,6-octadienal(Geranial)12345678HOHOCHOHOCHOCyclopentane-carbaldehydetrans-4-Hydroxycyclo-hexanecarbaldehyde14 CHOC6H5CHOtrans-3-Phenyl-2-propenal(Cinnamaldehyde)Benzaldehyde18-18-7Nomenclature: KetonesNomenclature: Ketones◆IUPAC names •the parent alkane is the longest chain that contains the carbonyl group•indicate the ketone by changing the suffix -e-eto -one-one•number the chain to give C=O the smaller number•the IUPAC retains the common names acetone, acetophenone, and benzophenonePropanone(Acetone)Benzophenone1-Phenyl-1-pentanoneAcetophenoneOOOO18-18-8Order of PrecedenceOrder of Precedence◆For compounds that contain more than one functional group indicated by a suffixHCOOHOCOOHOCOOHHOOHHSCOOHNH2Functional GroupCarboxyl-oic acidAldehyde-aloxo-Ketone-oneoxo-Alcohol-olhydroxy-Amino-amineamino-3-Oxopropanoic acid3-Oxobutanoic acid4-Hydroxybutanoic acid3-Aminobutanoic acidExample when the functional group has a lower prioritySulfhydryl-thiolmercapto2-MercaptoethanolSuffix if higherpriorityPrefix iflowerpriorityIncreasing precedence18-18-9Common NamesCommon Names•for an aldehyde, the common name is derived from the common name of the corresponding carboxylic acid•for a ketone, name the two alkyl or aryl groups bonded to the carbonyl carbon and add the word ketoneHCHOHCOHOCH3CHOCH3COHOFormaldehydeFormic acidAcetaldehydeAcetic acidEthyl isopropyl ketoneDiethyl ketoneDicyclohexyl ketoneOOO18-...
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Chapter18 - 18-18-1Aldehydes Aldehydes&& 18Chapter...

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