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Samenvatting organische chemie hoofdstuk 5-10
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Organische chemie, 1e bach geneeskunde hoofdstuk 5 tem 10 alle soorten reacties samengevat met foto's erbij.
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Organische chemieH5 substitutie:
Nucleofiel + elektrofiel-leaving groep -> nucleofiel-elektrofiel + leaving groep (neg lading)
Nucleofielen: H- , HO- , RO- , HS- , RS- , CN- , RCOO- , R3C- , R-MgBr+ , RSH , ROR , ROH , H2O ,
H3N
Elektrofielen: H+ , H3O+ , R3C+ , AlCl3
Leaving groepen: I- , Br- , Cl- F- , RCOO- , RO-
SN2:
Bij primaire koolstoffen
In 1 stap via transitietoestand
Walden inversie
Bimoleculair: nucleofiel + elektrofiel-leaving
Stereoselectief : 1 stereo-isomeer
Sterke elektronendonors als nucleofiel (Sterke Lewis base)
Leaving groep: sterke affiniteit voor afgegeven elektron
Minimale ruimtelijke hinder
SN1:
Unimoleculair: elektrofiel-leaving
Niet stereoselectief: 2 stereoisomeren (racemisch mengsel)
Meerdere stappen
1. Heterolytische splisting -> carbokation
2. Nucleofiele aanval (water)
Meer omringing alkylketens voor carbokation
Goede leaving groep: zelf dissociatie
Polaire solventen
Goede nucleofiel: geladen sterker, toenemend met stijgende periode
, H6: eliminatie
Elektrofiel-leaving + nucleofiel-alkalimetaal -> elektrofiel met =
E2:
Twee sigma bindingen breken -> pi binding
C-H + base
C-X uitstoten leaving groep
Dubbele binding omringd door meeste zijgroepen (Zaytseff)
Regels identiek aan SN2
E1:
Leaving groep verlaat molecule of proton
Eliminatie van water:
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