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Samenvatting cel I:organische chemie Hoofdstuk 6 $3.21
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Samenvatting cel I:organische chemie Hoofdstuk 6

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Samenvatting cel I:organische chemie Hoofdstuk 6

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  • July 31, 2021
  • 3
  • 2020/2021
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6. Organische reactiviteit – Eliminatie


 Verwachting: 1-broombutaan + natriumethanolaat → ethoxybutaan + NaBr
 Echter: ook vorming kleine hoeveelheid 1-buteen door eliminatie van HBr uit broomalkaan
 2 mechanismen:

 E2-mechanisme: belangrijkste
 E1-mechanisme

1. Het E2-mechanisme


 Reactie van tweede orde: afhankelijk van
 concentratie substraat
 tweede reactant dat optreedt als base


 Bimoleculair proces: beide reactanten komen tussen in transitietoestand:


B: + H-CR2-CXR2 → B---H---CR2∷∷CR2---X → CR2=CR2 + B-H + :X-


 Twee bindingen worden gebroken:
o De C-H binding m.b.v. de base
o De C-X binding via uitstoten van de leavinggroep


 vier groepen op het centrale C-atoom worden gezamenlijk coplanair


 Uiteindelijke vorming van de dubbele binding


 Voorbeeld: snelle vorming propeen bij reactie 2-broompropaan met natriumethanolaat; zie
ook vb. p. 87
 Er wordt overgegaan va 4 sp3 naar één p en 3 sp2-orbitalen

 Regel van Zaytseff: bij eliminatie wordt bij voorkeur het meer stabiele, meest
gesubstitueerde alkeen gevormd (omringd door de meeste zijgroepen)


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