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15.13
PreparationofThiols
NomenclatureofThiols1) analogoustoalcohols,butsuffixis-thiolratherthan-ol2) final-eofalkanenameisretained,notdroppedaswithalcohols
NomenclatureofThiols1) analogoustoalcohols,butsuffixis-thiolratherthan-ol2) final-eofalkanenameisretained,notdroppedaswithalcoholsCH3CHCH2CH2SHCH33-Methyl-1-butanethiol
ThiolsarepreparedfromalkylhalidesSN2usingthioureaassourceofnucleophilic
sulfurtheproductisanisothiouroniumsalt???
?H2NSH2NC?????
?RX???
?H2NSH2NC??R??+??+??
Thiolsarepreparedfromalkylhalides???
?H2NSH2NC??R??+??hydrolysisinbaseconvertstheisothiouroniumsalt
tothedesiredthiolNaOHH2O???
?H2NOH2NC?????
?R+??HS????
CH3(CH2)4CH2BrCH3(CH2)4CH2SH1-Hexanethiol(84%)1.(H2N)2CS2.NaOHExample
15.14
PropertiesofThiols
1.lowmolecularweightthiolshavefoulodors2.hydrogenbondingismuchweakerinthiolsthan
inalcohols3.thiolsarestrongeracidsthanalcohols4.thiolsaremoreeasilyoxidizedthanalcohols;
oxidationtakesplaceatsulfurPropertiesofThiols
havepKasofabout10;canbedeprotonatedin
aqueousbase..strongeracid
(pKa=10)weakeracid
(pKa=15.7)ThiolsarestrongeracidsthanalcoholsHRS????????OH?
?–RS????H????OH?
?–++
OxidationofthiolstakeplaceatsulfurthioldisulfideRS????HRS????SR???? thiol-disulfideredoxpairisimportantinbiochemistry otheroxidativeprocessesplace1,2,or3oxygenatomsonsulfur
OxidationofthiolstakeplaceatsulfurthioldisulfidesulfinicacidsulfonicacidRS????HRS????SR????sulfenicacidRS????OHRS????OHO?
??
?–+RS??OHO?
??
?–2+??O?
??
?–
HSCH2CH2CH(CH2)4COHSHO2,FeCl3(CH2)4COHa-Lipoicacid(78%)Example:sulfide-disulfideredoxpairOOSS
15.15
SpectroscopicAnalysisofAlcohols
O—Hstretching:3200-3650cm–1(broad)C—Ostretching:1025-1200cm–1(broad)InfraredSpectroscopy
FrancisA.Carey,OrganicChemistry,FourthEdition.Copyright?2000TheMcGraw-HillCompanies,Inc.Allrightsreserved.20003
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