, Nucleofiel – elektrofiel – radicaal...............................................................................................................5
Nucleofiel...............................................................................................................................................................5
Elektrofiel...............................................................................................................................................................5
Radicaal...................................................................................................................................................................6
Additie – eliminatie – substitutie...............................................................................................................6
Additie......................................................................................................................................................................6
Eliminatie...............................................................................................................................................................6
Substitutie.............................................................................................................................................................6
Regioselectiviteit – stereoselectiviteit....................................................................................................6
Regioselectiviteit..............................................................................................................................................6
Stereoselectiviteit............................................................................................................................................6
Elektrofiele additie...................................................................................................................................................7
Algemeen...................................................................................................................................................................7
Reactiemechanisme...........................................................................................................................................7
Stap 1.........................................................................................................................................................................7
Stap 2........................................................................................................................................................................7
Reactiemechanisme waterstofhalogeniden....................................................................................8
Bespreking............................................................................................................................................................8
Regioselectieve reactie.....................................................................................................................................8
Regel van Markovnikov...............................................................................................................................8
Verklaring..............................................................................................................................................................8
Niet-stereoselectieve reactie........................................................................................................................8
Stereoselectiviteit en enantiomeren.................................................................................................8
Stereoselectiviteit en diastereomeren.............................................................................................8
Elektrofiele additie van water in zuur midden...............................................................................8
Mechanisme........................................................................................................................................................8
Selectiviteit...........................................................................................................................................................9
Besluit.......................................................................................................................................................................9
Elektrofiele additie van dihalogenen.....................................................................................................9
Belang van polair solvent...........................................................................................................................9
Mechanisme........................................................................................................................................................9
Verloopt stereoselectief.............................................................................................................................10
Nucleofiele additie...................................................................................................................................................11
Algemeen...................................................................................................................................................................11
Anion nucleofielen..............................................................................................................................................11
Mechanisme........................................................................................................................................................11
, Alkyl anion,R-, als nucleofiel.....................................................................................................................11
H- als nucleofiel.................................................................................................................................................11
Niet-stereoselectieve reactie..................................................................................................................12
Neutrale nucleofielen......................................................................................................................................12
Mechanisme.......................................................................................................................................................12
Synthese van acetaal en ketaal............................................................................................................12
Synthese van imine......................................................................................................................................14
Nucleofiele substitutie.........................................................................................................................................15
Reactietype SN2.....................................................................................................................................................15
Mechanisme.......................................................................................................................................................15
Stereoselectiviteit...........................................................................................................................................15
Reactietype SN1......................................................................................................................................................15
Mechanisme.......................................................................................................................................................15
Stereoselectiviteit...........................................................................................................................................16
Snelheidsbepalende factoren....................................................................................................................16
Invloed van substraat..................................................................................................................................16
Invloed van de leaving groep................................................................................................................17
Invloed van het nucleofiel........................................................................................................................17
Invloed van het solvent..............................................................................................................................17
Bepalen van het reactiemechanisme..................................................................................................18
Eliminatie.......................................................................................................................................................................19
Algemeen.................................................................................................................................................................19
Reactietype E2......................................................................................................................................................19
Mechanisme......................................................................................................................................................19
Regioselectiviteit............................................................................................................................................19
Stereoselectiviteit...........................................................................................................................................19
Reactietype E1......................................................................................................................................................20
Mechanisme.....................................................................................................................................................20
Regioselectiviteit...........................................................................................................................................20
Bepalen van reactiemechanisme..........................................................................................................20
Competitie substitutie – eliminatie........................................................................................................21
Overzicht...............................................................................................................................................................21
Nucleofiele acylsubstitutie...............................................................................................................................22
Algemeen.................................................................................................................................................................22
Nucleodiele acylsubstitutie met anion nucleofielen...............................................................22
Algemeen reactiemechanisme...........................................................................................................22
, Evenwichtsligging........................................................................................................................................23
Nucleofiele acylsubstitutie aan carbonzuren en geladen nucleofielen....................23
Nucleofiele acetylsubstitutie met neutrale nucleofielen.....................................................23
Anhydriden en zuurhalogeniden.......................................................................................................23
Esters, carbonzuren en amiden..........................................................................................................23
Belangrijke toepassingen............................................................................................................................23
Verestering.........................................................................................................................................................23
Omestering.......................................................................................................................................................24
Hydrolyse van een ester............................................................................................................................25
Verzeping van een ester...........................................................................................................................25
Radicaal reacties......................................................................................................................................................27
Algemeen................................................................................................................................................................27
Algemeen reactiemechanisme...............................................................................................................27
Radicalaire substitutie....................................................................................................................................27
Mechanisme......................................................................................................................................................27
Regioselectiviteit...........................................................................................................................................28
Stereoselectiviteit..........................................................................................................................................28
Radicalaire additie.............................................................................................................................................28
Mechanisme.....................................................................................................................................................28
regioselectiviteit.............................................................................................................................................29
Stereoselectiviteit..........................................................................................................................................29
Radicalaire additie vs. elektrofiele additie..................................................................................29
Reductie en oxidatie reacties in organische chemie....................................................................30
Oxidatie- en reductiereacties in organische chemie...............................................................30
Oxidatie................................................................................................................................................................30
Reductie...............................................................................................................................................................30
Zuren en basen in organische chemie....................................................................................................32
Organische zuren en zuursterkte...........................................................................................................32
Zuur gedrag en ladingsdensiteit.......................................................................................................32
Zuur gedrag en elektronegativiteit..................................................................................................32
Zuur gedrag en mesomerie...................................................................................................................32
Zuur gedrag en nabij inductief effect.............................................................................................33
Zuur – base reacties in organische chemie....................................................................................34
Algemeen...........................................................................................................................................................34
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