pKa Chart 1 2 conjugate acid conjugate base conjugate acid ...

Acidhydroiodic acidhydrobromic acidprotonatedetherprotonatedalcoholhydr onium ionnitric acidhydrofluoric acidhydrogen nitridecarboxylic acidsprotonated acidtosic Chartconjugate acidconjugate baseconjugate acidconjugate basestrongest acidsweakest baseshydrogen sulfide12(bicarbonate)-7hydrochloric acidcarbocations-3 OOOHHNHHHCNHNH2 OHHH3 CNHHHSHHCO3-NHHHCNSCO3-2 NHOOOH3 CNHHOHHOHOHHHOOCCHNRHHOOHHHOOHOONRHOCCOM gBr16thiolsprimary alcoholsammonia/amines36(amide bases)(alkoxides)hydrogen35one way onlyone way onlyalkanes(Grignards/ organolithium reagents)~6018alkynes26ketonesesters(eno lates) cyanidetertiary alcohols10phenols91, amineswatercyclopentadieneamides(aromati c)1515conjugate acidconjugate baseconjugate acidconjugate base(hydroxide)(tert-butoxide)(ester enolates)strongest basesweakest acids34(acetylide anions)(hydride)(cyanide) ions

alkynes 26 ketones esters (enolates) 18-21 25 hydrogen cyanide 9.1 tertiary alcohols phenols 10 1,3-diketones 9 10.5 10.6 15.7 protonated amines water cyclopentadiene amides (aromatic) 15 15 conjugate acid conjugate base conjugate acid conjugate base (hydroxide) (tert-butoxide) (ester enolates) s t r o n g e s t b a s e s w e a k e s t a c i d ...

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www.csus.edu

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