苯取代衍生物及其命名法columbia有机化学课件09 html1.pptxVIP

11.7

SubstitutedDerivativesofBenzene

andTheirNomenclature

1)Benzeneisconsideredastheparentand

comeslastinthename.GeneralPoints

ExamplesBromobenzenetert-ButylbenzeneNitrobenzeneNO2C(CH3)3Br

1)Benzeneisconsideredastheparentand

comeslastinthename.2)Listsubstituentsinalphabeticalorder3)Numberringindirectionthatgiveslowest

locantatfirstpointofdifferenceGeneralPoints

2-bromo-1-chloro-4-fluorobenzeneExampleBrClF

Ortho,Meta,andParaalternativelocantsfordisubstituted

derivativesofbenzene1,2=ortho

(abbreviatedo-)1,3=meta

(abbreviatedm-)1,4=para

(abbreviatedp-)

Exampleso-ethylnitrobenzeneNO2CH2CH3ClClm-dichlorobenzene(1-ethyl-2-nitrobenzene)(1,3-dichlorobenzene)

Certainmonosubstitutedderivativesofbenzene

haveuniquenamesTable11.1(p407)

BenzaldehydeTable11.1(p407)CHO

BenzoicacidTable11.1(p407)COHO

StyreneTable11.1(p407)CH2CH

AnisoleTable11.1(p407)OCH3

AcetophenoneTable11.1(p407)CCH3O

PhenolTable11.1(p407)OH

AnisoleTable11.1(p407)OCH3

AnilineTable11.1(p407)NH2

NamesinTable11.1canbeusedasparentOCH3NO2OCH3Anisolep-Nitroanisole

or

4-Nitroanisole

EasilyconfusednamesphenylphenolbenzylOHCH2—

11.8

PolycyclicAromaticHydrocarbons

resonanceenergy=255kJ/molmoststableLewisstructure;

bothringscorrespondto

KekulébenzeneNaphthalene

AnthracenePhenanthreneresonanceenergy:347kJ/mol381kJ/molAnthraceneandPhenanthrene

11.9

PhysicalPropertiesofArenes

Resembleotherhydrocarbons nonpolar insolubleinwater lessdensethanwaterPhysicalProperties