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  • Universiteit Gent (UGent)
  • Geneeskunde
  • Cel I : Fysische en chemische grondslagen (D012571)
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samenvatting organische chemie H4 en H5

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2022/2023 Written for academic year
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Universiteit Gent (UGent)
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Cel I : Fysische en chemische grondslagen (D012571)
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samenvatting organische chemie H4 en H5 lessen en cursus van prof Frederic Lynen

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4.inleiding tot reactiviteit-organische aciditeit en
basiciteit
- Proton-transferevenwichten (Brönsted-Lowry concept)
 Zuur=proton-donor
 Base=proton-acceptor
 Ka, pKazuurtegraad
 pHzuurtegraad in waterig midden
o hoe meer dissociëren in water, hoe zuurder
 water pKa schaal (-216)
o H3O+sterkste zuurpKa=-2
o OH-sterkste basepKa=16
 organische pKa-schaal(-1050)
o HIsterkste zuurpKa=-10
o CH4sterkste basepKa=50
 Zuurtegraad neemt toe
o Stabiliteit zuur neemt af
 H op grotere molecule gebonden
 Grotere elektronegativiteit
 Sterk EN atoom ipv H-atoom
 Zuurtegraad neemt af
o Instabiele base
 Goed nucleofiel!!

- Oxyzuren
 Alcoholen en carbonzuren ( OH en COOH)
o Groot verschil in zuurtegraad
 Stijgt wanneer formele lading positiever is
o Alcoholen
 zwak zuur
 Waterige opl niet zuur
 Sterke geconjugeerde base,
o Instabiel doordat – lading op 1 atoom ligt
o Geen mogelijkheid tot delokalisatie
o Carbonzuren
 Sterkste zuur in lichaam
 Stabiele geconjugeerde base
o Mogelijkheid tot delokalisatie
o Soms minder delokalisatie

 Vb fenol
 Aromatische structuur
o Verspringen van O naar C minder voordelig
o Zou aromaticiteit verliezen
o Inductief effect
 Door delokalisatie stabiliserend dichter dan destabiliserende
o Wegens EN alkanen, elektronzuigende groepen

9

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