inleiding tot reactiviteit organische aciditeit en
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Universiteit Gent (UGent)
Geneeskunde
Cel I : Fysische en chemische grondslagen (D012571) (D012571)
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Organische
Chemie
,Organische Chemie
1.Stereochemie I:de ruimtelijke structuur van het koolstofskelet..........................................................2
Hybridisatie:.......................................................................................................................................2
Alkanen...............................................................................................................................................2
Newmanprojectie...............................................................................................................................2
Alkenen en alkynen............................................................................................................................4
Cyclische verbindingen.......................................................................................................................4
2. Stereo-isomerie en stereochemie- Het belang van de derde dimensie in de chemie.........................6
3. inleiding tot organische reactiviteit: chemische transformaties.........................................................8
4.inleiding tot reactiviteit-organische aciditeit en basiciteit...................................................................9
Proton-transferevenwichten (Brönsted-Lowry concept)....................................................................9
Oxyzuren............................................................................................................................................9
5.organische reactiviteit: nucleofiele substitutie..................................................................................10
SN2-mechanisme...............................................................................................................................10
SN1-mechanisme...............................................................................................................................11
6. Organische reactiviteit: eliminatie....................................................................................................12
Het E2 mechanisme..........................................................................................................................12
E1-mechanisme................................................................................................................................12
7. organische reactiviteit: additie aan de dubbele binding (additiereacties)........................................14
8. organische reacties: radicaalreacties................................................................................................16
9. organische reactiviteit; reactiviteit van de carbonylfunctie..............................................................17
Hydratatie van Aldehyden en ketonen (additie van H2O)................................................................17
Additie van alcoholen met vorming van (hemi-)acetalen of (hemi-)ketalen....................................17
Nucleofiele additie van amines.........................................................................................................18
Keto-enol tautomerie.......................................................................................................................19
De aldolcondensatie.........................................................................................................................19
10.Organische reactiviteit: de carboxylgroep en afgeleide functionele groepen.................................20
Derivaten van carbonzuur................................................................................................................21
Fosfo-esters en fosfo-anhydriden.....................................................................................................22
11. Redoxreacties.................................................................................................................................23
Oxidatie............................................................................................................................................23
Reductie............................................................................................................................................23
1
, Organische chemie
1.Stereochemie I:de ruimtelijke structuur van het
koolstofskelet
- Hybridisatie:
Sp³: 4 sigma-bindingen, 109°
Sp²: 3 sigma-bindingen, 120°
Sp: 2 sigma-bindingen, 180°
Ruimtelijke structurenfysische eigenschappen
o Vb celwand
Rechte ketendichter stapelen, meer reactie
In echt bewegingniet steeds dezelfde hoeken (kin E)
- Alkanen
Methaan: CH3
Ethaan:
o Verschillende vormen
Geëclipseerd: elke C-H tegenover C-H naburig atoom
o Meer E, meer sterische hinder
o Komt minder voor(minder stabiel)
Geschrankt: niet elke C-H tegenover C-H naburig atoom
o Minst E, minder sterisch hinder
Geen E-verlies bij wissel, wel E nodig
o Conformeren: door rotatie van ene naar andere molecule
Butaan:
o Methyl groepen tov elkaar
o Gauche: in een hoek van 60°, 300° lage E
Per gauche conf + 3,5 kJ
Twee gauche conformaties
o Anti: hoek van 180°minst E
o Geëclipseerd: meeste E
o Andere niet cyclische alkanen hieruit opgedeeld
Sigma binding vrije draaibaarheid
- Newmanprojectie
Geëclipseerd
o Torsiehoek=0°
Geschrankt
o Torsiehoek=60°
2
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