Organische chemie
1Ba DGK
2025 - 2026
Nienke Van Boxelaer
,Inhoud
Hoofdstuk 1: Inleiding ....................................................................................................................................................................7
Geschiedenis .................................................................................................................................................... 7
Waarom organische chemie? ............................................................................................................................... 7
Cruciale informatie ............................................................................................................................................ 8
Typen bindingen ........................................................................................................................................... 8
Ruimtelijke structuur..................................................................................................................................... 9
Voorstelling van organische structuurformules ..................................................................................................... 10
Brutoformule ............................................................................................................................................. 10
Structuurformule ........................................................................................................................................ 10
Skeletstructuur ........................................................................................................................................... 11
Oxidatiegraad ................................................................................................................................................. 11
Hoofdstuk 2: Inleiding tot organische verbindingen ................................................................................................................12
Alkanen = Verzadigde koolwaterstoffen.............................................................................................................. 12
Acyclische alkanen ..................................................................................................................................... 12
Cycloalkanen ............................................................................................................................................. 14
Sp3-Hybridisatie ......................................................................................................................................... 15
Alkylhalogeniden, alkylhaliden of halogeenalkanen......................................................................................... 15
Ethers ............................................................................................................................................................ 16
Lineaire ethers ........................................................................................................................................... 16
Cyclische ethers ......................................................................................................................................... 17
Kroonethers ............................................................................................................................................... 17
Alcoholen ...................................................................................................................................................... 18
Amines .......................................................................................................................................................... 19
Lineaire amines .......................................................................................................................................... 19
Quaternaire ammoniumzouten ...................................................................................................................... 21
Cyclische amines ........................................................................................................................................ 21
Fysische eigenschappen van alkanen, alkylhaliden, ethers, alcoholen en aminen ....................................................... 22
Kookpunt .................................................................................................................................................. 22
Smeltpunt .................................................................................................................................................. 24
Oplosbaarheid ............................................................................................................................................ 24
Structuur van alkanen ...................................................................................................................................... 26
Projecties van alkanen ................................................................................................................................. 26
Conformaties van alkanen ............................................................................................................................ 26
Structuur van cycloalkanen ............................................................................................................................... 28
Cyclopropaan, -butaan & -pentaan ................................................................................................................ 28
Cyclohexaan .............................................................................................................................................. 29
Stoelvorm tekenen ...................................................................................................................................... 30
Monogesubstitueerd cyclohexaan .................................................................................................................. 31
1
, Digesubstitueerd cyclohexaan ...................................................................................................................... 31
Bicyclische & polycyclische systemen ........................................................................................................... 32
Functionele groepen ........................................................................................................................................ 33
Hoofdstuk 3: Alkenen & alkynen = Onverzadigde koolwaterstoffen.....................................................................................34
Inleiding ........................................................................................................................................................ 34
Hybridisatie.................................................................................................................................................... 34
Sp2-hybridisatie bij alkenen.......................................................................................................................... 34
Sp-Hybridisatie bij alkynen .......................................................................................................................... 35
Nomenclatuur ................................................................................................................................................. 36
Systematisch .............................................................................................................................................. 36
E/Z-nomenclatuur van alkanen ..................................................................................................................... 39
Gebruiksnamen .......................................................................................................................................... 41
Fysische eigenschappen van alkenen & alkynen .................................................................................................. 42
Diënen & polyenen.......................................................................................................................................... 42
Resonantie................................................................................................................................................. 44
Geconjugeerde polyenen & kleur .................................................................................................................. 46
Terpenen ................................................................................................................................................... 48
Hoofdstuk 4: Aromaten ................................................................................................................................................................51
Inleiding ........................................................................................................................................................ 51
Structuur van benzeen ...................................................................................................................................... 51
Nomenclatuur benzeenderivaten ........................................................................................................................ 52
Monogesubstitueerde derivaten..................................................................................................................... 52
Digesubstitueerde derivaten ......................................................................................................................... 52
Meer dan 2 substituenten ............................................................................................................................. 52
Benzeen in substituent ................................................................................................................................. 53
Aromaticiteit .................................................................................................................................................. 53
Voorwaarden aromatische formules: .............................................................................................................. 53
Voorwaarden anti-aromaticiteit ..................................................................................................................... 53
Niet-aromatische moleculen ......................................................................................................................... 54
Vergelijking stabiliteit ................................................................................................................................. 54
Annulenen...................................................................................................................................................... 54
Polyaromaten = Polycyclische aromatische koolwaterstoffen (PAK) ....................................................................... 55
Heteroaromaten .............................................................................................................................................. 55
Pyridine .................................................................................................................................................... 56
Pyrrool & porfyrine-ringsysteem................................................................................................................... 57
Furaan & thiofeen ....................................................................................................................................... 58
Chinoline, indool, imidazool, purine & pyrimidine .......................................................................................... 58
Hoofdstuk 5: Stereochemie ..........................................................................................................................................................60
Inleiding ........................................................................................................................................................ 60
Conformationele isomeren = Conformeren.......................................................................................................... 60
2
, Configurationele isomeren ................................................................................................................................ 60
Chiraliteit .................................................................................................................................................. 61
Stereoisomeren tekenen.................................................................................................................................... 61
Enantiomeren (Configurationele stereoisomeren) ................................................................................................. 62
Diastereomeren (Configurationele stereoisomeren) .............................................................................................. 64
Epimeren................................................................................................................................................... 64
Mesomeren .................................................................................................................................................... 65
Optische activiteit ........................................................................................................................................... 65
Fysische eigenschappen van stereoisomeren ........................................................................................................ 66
Chiraliteit & geneesmiddelen ............................................................................................................................ 67
Hoofdstuk 6: Zuren & basen .......................................................................................................................................................68
Inleiding ........................................................................................................................................................ 68
Evenwichtsligging van een zuur-basereactie........................................................................................................ 68
Zuur of base? .................................................................................................................................................. 69
Effect van de structuur op de pKa....................................................................................................................... 70
Inleiding.................................................................................................................................................... 70
Resonantie................................................................................................................................................. 70
Elektronegativiteit ...................................................................................................................................... 74
Atoomgrootte ............................................................................................................................................. 74
Hybridisatie ............................................................................................................................................... 74
Inductieve effecten...................................................................................................................................... 75
Lading ...................................................................................................................................................... 76
Algemeen overzicht effect op de pKa ............................................................................................................. 76
Basische eigenschappen van heteroaromaten ....................................................................................................... 77
Pyridine & imidazool .................................................................................................................................. 77
Pyrrool ...................................................................................................................................................... 77
Effect van de pKa op de structuur van de organische formule ................................................................................. 78
Hoofdstuk 7: Organische reacties (deel 1) .................................................................................................................................79
Inleiding ........................................................................................................................................................ 79
Elektrofiele additiereactie aan alkenen................................................................................................................ 81
Algemeen .................................................................................................................................................. 81
Additie van waterstofhalogeniden (HX) ......................................................................................................... 82
Additie van water ....................................................................................................................................... 83
Additie van alcoholen.................................................................................................................................. 84
Additie van halogenen ................................................................................................................................. 84
Additiereactie van waterstof aan alkenen en alkynen ............................................................................................ 85
Metaalgekatalyseerde cycloadditiereactie aan alkynen .......................................................................................... 86
Elektrofiele aromatische substitutie .................................................................................................................... 87
Algemeen .................................................................................................................................................. 87
3
, Substitutie aan benzeen ............................................................................................................................... 87
Substitutie aan een gesubstitueerd benzeen ..................................................................................................... 88
Substitutie aan heteroaromaten ..................................................................................................................... 92
Diazoniumzouten als elektrofielen ................................................................................................................ 92
Radicalaire substitutiereacties aan alkanen en ethers ............................................................................................. 94
Halogenering van alkanen ............................................................................................................................ 94
Radicalaire substitutiereactie van ethers met zuurstofgas .................................................................................. 95
Nucleofiele substitutiereacties van alkylhalogeniden en alcoholen .......................................................................... 96
Inleiding.................................................................................................................................................... 96
Sn2-reactie ................................................................................................................................................. 96
Invloed van het nucleofiel op de SN2-reactie ................................................................................................... 98
SN1-reactie ................................................................................................................................................ 98
Invloed van de leaving-group op de SN2- & SN1-reactie ..................................................................................100
Biologische leaving-groepen .......................................................................................................................101
Vergelijking tussen SN2 & SN1.....................................................................................................................102
Reactieproducten van nucleofiele substitutiereacties van alkylhalogeniden.........................................................102
Reactie van alcoholen met waterstofhalogeniden ............................................................................................103
Eliminatiereacties E1 en E2 .............................................................................................................................104
Dehydrohalogenering tot alkenen .................................................................................................................104
Substitutie & eliminatie in competitie ...........................................................................................................105
Dehydratatie van alcoholen tot alkenen .........................................................................................................106
Regel van Zaitsev ......................................................................................................................................107
Oxidatie- & reductiereacties ............................................................................................................................108
Inleiding...................................................................................................................................................108
Additie van zuurstof via peroxycarbonzuur ...................................................................................................108
Additiereactie van zuurstof aan PAK’s ..........................................................................................................109
Oxidatie van alkylgroepen op een benzeenring ...............................................................................................110
Oxidatie van alcoholen en hydrochinonen .....................................................................................................110
Hoofdstuk 8: Aldehyden, ketonen, carbonzuren & hun derivaten ....................................................................................... 111
Inleiding .......................................................................................................................................................111
Nomenclatuur ................................................................................................................................................112
Aldehyden – RCHO of CH2O ......................................................................................................................112
Ketonen – RCOR’ .....................................................................................................................................112
Carbonzuren – RCOOH ..............................................................................................................................113
Zouten .....................................................................................................................................................114
Esters – RCOOR’ = RCO2R’ .......................................................................................................................115
Zuurhalogeniden = Acylhalogenide - RCOX..................................................................................................115
Zuuranhydriden .........................................................................................................................................116
Amiden ....................................................................................................................................................116
4
, Nitrillen ...................................................................................................................................................117
Moleculen met meervoudige bindingen & functionele groepen .........................................................................117
De carbonylgroep ...........................................................................................................................................117
Fysische eigenschappen ..................................................................................................................................118
Kookpunt .................................................................................................................................................118
Oplosbaarheid ...........................................................................................................................................118
Biologische functies van carbonylverbindingen ..................................................................................................119
Vetzuren ...................................................................................................................................................119
Zepen ......................................................................................................................................................120
Wassen.....................................................................................................................................................121
Vetten & oliën ...........................................................................................................................................122
Intermezzo................................................................................................................................................122
Fosfoglyceriden & sfingolipiden ..................................................................................................................123
Hoofdstuk 9: Organische reacties (deel 2) ...............................................................................................................................125
Inleiding .......................................................................................................................................................125
Keto-enol-tautomerie ......................................................................................................................................125
Nucleofiele addities aan carbonylgroepen ..........................................................................................................127
Additie van water ......................................................................................................................................128
Additie van alcoholen.................................................................................................................................129
Additie van stikstofnucleotiden ....................................................................................................................130
Aldolcondensatie ...........................................................................................................................................131
Biologische aldolcondensatie ......................................................................................................................131
Oxidatie- & reductiereacties met carbonylverbindingen .......................................................................................132
Oxidatiereacties.........................................................................................................................................132
Reductiereacties ........................................................................................................................................133
Hoofdstuk 10: Organische reacties (deel 3) .............................................................................................................................134
Omzetting van carbonzuren in zouten ................................................................................................................134
Decarboxylering ............................................................................................................................................134
Deprotonering, decarboxylering & dehydraterig van dicarbonzuren .......................................................................134
Deprotonering ...........................................................................................................................................134
Bereiding van esters .......................................................................................................................................135
Verestering ...............................................................................................................................................135
Methylering ..............................................................................................................................................136
Hydrolyse van esters .......................................................................................................................................136
Zuurgekatalyseerde hydrolyse .....................................................................................................................136
Verzeping van esters ..................................................................................................................................137
Omestering = Transesterificatie ........................................................................................................................137
Aminolyse van een ester..................................................................................................................................138
Hydrolyse & alcoholyse van amiden .................................................................................................................139
5
, Hydrolyse van nitrillen tot carbonzuren .............................................................................................................140
Claisencondensatie .........................................................................................................................................140
Oxidatie- & reductiereacties met carbonzuren en carbonzuurderivaten ...................................................................141
Oxidatiereacties.........................................................................................................................................141
Reductiereacties ........................................................................................................................................141
Geactiveerde acylverbindingen.........................................................................................................................141
Zuurhalogeniden .......................................................................................................................................142
Zuuranhydriden .........................................................................................................................................143
Thio-esters: De acylactiverende groepen van de natuur ........................................................................................143
Hoofdstuk 11: Polyfunctionele verbindingen ..........................................................................................................................145
Inleiding .......................................................................................................................................................145
Koolhydraten of sacchariden ............................................................................................................................145
Inleiding...................................................................................................................................................145
Classificatie van koolhydraten .....................................................................................................................145
Configuratie van monosacchariden...............................................................................................................146
Configuraties van de aldosen .......................................................................................................................147
Configuraties van de ketosen .......................................................................................................................147
Reacties met monosacchariden ....................................................................................................................148
Cyclische structuur van monosacchariden .....................................................................................................148
Disacchariden ...........................................................................................................................................150
Zoetstoffen ...............................................................................................................................................151
Polysacchariden ........................................................................................................................................152
Andere belangrijke koolhydraten .................................................................................................................153
Aminozuren ..................................................................................................................................................153
Inleiding...................................................................................................................................................153
Eigenschappen ..........................................................................................................................................155
Peptidebinding ..........................................................................................................................................156
Decarboxylering ........................................................................................................................................156
Reactiemechanismen overzicht .................................................................................................................................................158
6
,Hoofdstuk 1: Inleiding
Geschiedenis
Organische chemie → Sinds oudheid:
o Stoffen extraheren uit planten & dieren als geneesmiddel
• Bv. “Aspirine” = Acetylsalicylzuur uit wilgen (salix) → Koortsverlagende,
pijnstillende eigenschappen
o Kleurstoffen extraheren uit planten
• Bv. Indigo uit indigofera tinctoria
Begin 19de eeuw:
o Idee van het vitalisme heerst:
• Levende organismen verschillen fundamenteel van niet-levende organismen,
omdat ze een onstoffelijke levenskracht (“Élan vital”) bevatten.
o Verbindingen worden opgedeeld in 2 groepen:
• Organisch: Afkomstig van levende dieren
• Anorganisch: Afkomstig van minerale oorsprong of niet-levende materie
o Overtuiging: Organische stoffen kunnen niet uit anorganische stoffen worden bereid.
1828:
o Friedrich Wöhler: Synthetiseerde ureum (organisch want metaboliet uit urine
zoogdieren) uit anorganische verbindingen
Synthese van ureum uit zilvercyanaat en ammoniumchloride
Heden:
o Organische (natuur)producten worden standaard gesynthetiseerd in laboratorium
Waarom organische chemie?
Organische chemie = Studie koolstofhoudende verbindingen
Koolstof:
o Midden 2de rij PSE
• Geeft noch ontvangt elektronen → Deelt
• Stabiele covalente bindingen (met andere koolstofatomen & meeste andere atomen)
o Basisbouwsteen leven op aarde
7
, o Kennis belangrijk in veel wetenschappelijke velden:
• Biochemie
• Medicinale chemie = Studie van ontwikkeling van medicijnen
• Farmacologie = Studie van effect medicijn op patiënt en omgekeerd
o Belangrijk in verschillende industriële velden:
• Voedingsindustrie:
▪ Bereiding bier
▪ Pesticiden & herbiciden
▪ Kleurstoffen
▪ Bewaarmiddelen
• Textielindustrie
▪ Brandvertragende en/of waterafstotende kledij
▪ kleurstoffen
• Materiaalindustrie
▪ Kunststoffen
▪ Ontwikkeling zelfherstellende materialen
▪ Voedselverpakkingen
• Farmacie
▪ Bereiding geneesmiddelen & behandelingen
▪ Modificeren cellen met fluorescerende kleurstoffen & actieve
farmaceutische stoffen
Cruciale informatie
Typen bindingen
Ionaire binding
o Elektronenoverdracht van ene naar andere atoom
• Metalen → Neiging om elektronen af te staan
• Niet-metalen → Neiging om elektronen op te nemen
o Resultaat elektrostatische aantrekking tss. ionen van tegengestelde lading
o Specifiek kristalrooster
o Bv. Natriumchloride
8
, Covalente binding
o Valentie-elektronen gemeenschappelijk stellen
o (Meestal 2) Elektronen delen → Gemeenschappelijk elektronenpaar
o Apolair of polair
Apolaire covalente binding
o Gelijke ladingsverdeling t.g.v. gelijke elektronegativiteit
o Bv. Waterstofgas (H2) en chloorgas (Cl2)
Polaire covalente binding
o Ongelijke ladingsverdeling t.g.v. verschillende elektronegativiteiten
o Meest elektronegatieve → Grootste ladingsdichtheid
• PSE → Hoe dichter bij fluor (rechtsboven), hoe hoger EN
o Partieel positieve & partieel negatieve lading → Heeft dipool
• Grootte: Aangeduid met dipoolmoment (µ)
• Richting: Aangeduid met pijltje (+ → -)
▪ 1 covalente binding: Dipoolmoment = Dipoolmoment binding
▪ Meerdere bindingen: Dipoolmoment = Dipoolmoment afh. van
dipoolmomenten ALLE bindingen + Geometrie (Vectoriële som)
➢ Dipoolmoment = 0 (Heffen elkaar op) → Molecule =
Apolair, bindingen polair
o Bv. Water (H2O), ammoniak (NH3), zoutzuur (HCl)
Algemeen:
o Ionaire binding ↔ Polair covalente binding ↔ Apolair covalente binding
• Hoe groter verschil in elektronegativiteit, hoe groter “ionaire karakter”
• Hoe kleiner verschil in elektronegativiteit, hoe groter “covalente karakter”
o Netto dipoolmoment molecule weten → Ruimtelijke structuur nodig!
Ruimtelijke structuur
Lewisstructuur
1. Zoek het totale aantal valentie-elektronen voor alle atomen in de molecule.
• Voeg 1 elektron toe voor elke negatieve lading
• Trek 1 elektron af voor elke positieve lading
9
1Ba DGK
2025 - 2026
Nienke Van Boxelaer
,Inhoud
Hoofdstuk 1: Inleiding ....................................................................................................................................................................7
Geschiedenis .................................................................................................................................................... 7
Waarom organische chemie? ............................................................................................................................... 7
Cruciale informatie ............................................................................................................................................ 8
Typen bindingen ........................................................................................................................................... 8
Ruimtelijke structuur..................................................................................................................................... 9
Voorstelling van organische structuurformules ..................................................................................................... 10
Brutoformule ............................................................................................................................................. 10
Structuurformule ........................................................................................................................................ 10
Skeletstructuur ........................................................................................................................................... 11
Oxidatiegraad ................................................................................................................................................. 11
Hoofdstuk 2: Inleiding tot organische verbindingen ................................................................................................................12
Alkanen = Verzadigde koolwaterstoffen.............................................................................................................. 12
Acyclische alkanen ..................................................................................................................................... 12
Cycloalkanen ............................................................................................................................................. 14
Sp3-Hybridisatie ......................................................................................................................................... 15
Alkylhalogeniden, alkylhaliden of halogeenalkanen......................................................................................... 15
Ethers ............................................................................................................................................................ 16
Lineaire ethers ........................................................................................................................................... 16
Cyclische ethers ......................................................................................................................................... 17
Kroonethers ............................................................................................................................................... 17
Alcoholen ...................................................................................................................................................... 18
Amines .......................................................................................................................................................... 19
Lineaire amines .......................................................................................................................................... 19
Quaternaire ammoniumzouten ...................................................................................................................... 21
Cyclische amines ........................................................................................................................................ 21
Fysische eigenschappen van alkanen, alkylhaliden, ethers, alcoholen en aminen ....................................................... 22
Kookpunt .................................................................................................................................................. 22
Smeltpunt .................................................................................................................................................. 24
Oplosbaarheid ............................................................................................................................................ 24
Structuur van alkanen ...................................................................................................................................... 26
Projecties van alkanen ................................................................................................................................. 26
Conformaties van alkanen ............................................................................................................................ 26
Structuur van cycloalkanen ............................................................................................................................... 28
Cyclopropaan, -butaan & -pentaan ................................................................................................................ 28
Cyclohexaan .............................................................................................................................................. 29
Stoelvorm tekenen ...................................................................................................................................... 30
Monogesubstitueerd cyclohexaan .................................................................................................................. 31
1
, Digesubstitueerd cyclohexaan ...................................................................................................................... 31
Bicyclische & polycyclische systemen ........................................................................................................... 32
Functionele groepen ........................................................................................................................................ 33
Hoofdstuk 3: Alkenen & alkynen = Onverzadigde koolwaterstoffen.....................................................................................34
Inleiding ........................................................................................................................................................ 34
Hybridisatie.................................................................................................................................................... 34
Sp2-hybridisatie bij alkenen.......................................................................................................................... 34
Sp-Hybridisatie bij alkynen .......................................................................................................................... 35
Nomenclatuur ................................................................................................................................................. 36
Systematisch .............................................................................................................................................. 36
E/Z-nomenclatuur van alkanen ..................................................................................................................... 39
Gebruiksnamen .......................................................................................................................................... 41
Fysische eigenschappen van alkenen & alkynen .................................................................................................. 42
Diënen & polyenen.......................................................................................................................................... 42
Resonantie................................................................................................................................................. 44
Geconjugeerde polyenen & kleur .................................................................................................................. 46
Terpenen ................................................................................................................................................... 48
Hoofdstuk 4: Aromaten ................................................................................................................................................................51
Inleiding ........................................................................................................................................................ 51
Structuur van benzeen ...................................................................................................................................... 51
Nomenclatuur benzeenderivaten ........................................................................................................................ 52
Monogesubstitueerde derivaten..................................................................................................................... 52
Digesubstitueerde derivaten ......................................................................................................................... 52
Meer dan 2 substituenten ............................................................................................................................. 52
Benzeen in substituent ................................................................................................................................. 53
Aromaticiteit .................................................................................................................................................. 53
Voorwaarden aromatische formules: .............................................................................................................. 53
Voorwaarden anti-aromaticiteit ..................................................................................................................... 53
Niet-aromatische moleculen ......................................................................................................................... 54
Vergelijking stabiliteit ................................................................................................................................. 54
Annulenen...................................................................................................................................................... 54
Polyaromaten = Polycyclische aromatische koolwaterstoffen (PAK) ....................................................................... 55
Heteroaromaten .............................................................................................................................................. 55
Pyridine .................................................................................................................................................... 56
Pyrrool & porfyrine-ringsysteem................................................................................................................... 57
Furaan & thiofeen ....................................................................................................................................... 58
Chinoline, indool, imidazool, purine & pyrimidine .......................................................................................... 58
Hoofdstuk 5: Stereochemie ..........................................................................................................................................................60
Inleiding ........................................................................................................................................................ 60
Conformationele isomeren = Conformeren.......................................................................................................... 60
2
, Configurationele isomeren ................................................................................................................................ 60
Chiraliteit .................................................................................................................................................. 61
Stereoisomeren tekenen.................................................................................................................................... 61
Enantiomeren (Configurationele stereoisomeren) ................................................................................................. 62
Diastereomeren (Configurationele stereoisomeren) .............................................................................................. 64
Epimeren................................................................................................................................................... 64
Mesomeren .................................................................................................................................................... 65
Optische activiteit ........................................................................................................................................... 65
Fysische eigenschappen van stereoisomeren ........................................................................................................ 66
Chiraliteit & geneesmiddelen ............................................................................................................................ 67
Hoofdstuk 6: Zuren & basen .......................................................................................................................................................68
Inleiding ........................................................................................................................................................ 68
Evenwichtsligging van een zuur-basereactie........................................................................................................ 68
Zuur of base? .................................................................................................................................................. 69
Effect van de structuur op de pKa....................................................................................................................... 70
Inleiding.................................................................................................................................................... 70
Resonantie................................................................................................................................................. 70
Elektronegativiteit ...................................................................................................................................... 74
Atoomgrootte ............................................................................................................................................. 74
Hybridisatie ............................................................................................................................................... 74
Inductieve effecten...................................................................................................................................... 75
Lading ...................................................................................................................................................... 76
Algemeen overzicht effect op de pKa ............................................................................................................. 76
Basische eigenschappen van heteroaromaten ....................................................................................................... 77
Pyridine & imidazool .................................................................................................................................. 77
Pyrrool ...................................................................................................................................................... 77
Effect van de pKa op de structuur van de organische formule ................................................................................. 78
Hoofdstuk 7: Organische reacties (deel 1) .................................................................................................................................79
Inleiding ........................................................................................................................................................ 79
Elektrofiele additiereactie aan alkenen................................................................................................................ 81
Algemeen .................................................................................................................................................. 81
Additie van waterstofhalogeniden (HX) ......................................................................................................... 82
Additie van water ....................................................................................................................................... 83
Additie van alcoholen.................................................................................................................................. 84
Additie van halogenen ................................................................................................................................. 84
Additiereactie van waterstof aan alkenen en alkynen ............................................................................................ 85
Metaalgekatalyseerde cycloadditiereactie aan alkynen .......................................................................................... 86
Elektrofiele aromatische substitutie .................................................................................................................... 87
Algemeen .................................................................................................................................................. 87
3
, Substitutie aan benzeen ............................................................................................................................... 87
Substitutie aan een gesubstitueerd benzeen ..................................................................................................... 88
Substitutie aan heteroaromaten ..................................................................................................................... 92
Diazoniumzouten als elektrofielen ................................................................................................................ 92
Radicalaire substitutiereacties aan alkanen en ethers ............................................................................................. 94
Halogenering van alkanen ............................................................................................................................ 94
Radicalaire substitutiereactie van ethers met zuurstofgas .................................................................................. 95
Nucleofiele substitutiereacties van alkylhalogeniden en alcoholen .......................................................................... 96
Inleiding.................................................................................................................................................... 96
Sn2-reactie ................................................................................................................................................. 96
Invloed van het nucleofiel op de SN2-reactie ................................................................................................... 98
SN1-reactie ................................................................................................................................................ 98
Invloed van de leaving-group op de SN2- & SN1-reactie ..................................................................................100
Biologische leaving-groepen .......................................................................................................................101
Vergelijking tussen SN2 & SN1.....................................................................................................................102
Reactieproducten van nucleofiele substitutiereacties van alkylhalogeniden.........................................................102
Reactie van alcoholen met waterstofhalogeniden ............................................................................................103
Eliminatiereacties E1 en E2 .............................................................................................................................104
Dehydrohalogenering tot alkenen .................................................................................................................104
Substitutie & eliminatie in competitie ...........................................................................................................105
Dehydratatie van alcoholen tot alkenen .........................................................................................................106
Regel van Zaitsev ......................................................................................................................................107
Oxidatie- & reductiereacties ............................................................................................................................108
Inleiding...................................................................................................................................................108
Additie van zuurstof via peroxycarbonzuur ...................................................................................................108
Additiereactie van zuurstof aan PAK’s ..........................................................................................................109
Oxidatie van alkylgroepen op een benzeenring ...............................................................................................110
Oxidatie van alcoholen en hydrochinonen .....................................................................................................110
Hoofdstuk 8: Aldehyden, ketonen, carbonzuren & hun derivaten ....................................................................................... 111
Inleiding .......................................................................................................................................................111
Nomenclatuur ................................................................................................................................................112
Aldehyden – RCHO of CH2O ......................................................................................................................112
Ketonen – RCOR’ .....................................................................................................................................112
Carbonzuren – RCOOH ..............................................................................................................................113
Zouten .....................................................................................................................................................114
Esters – RCOOR’ = RCO2R’ .......................................................................................................................115
Zuurhalogeniden = Acylhalogenide - RCOX..................................................................................................115
Zuuranhydriden .........................................................................................................................................116
Amiden ....................................................................................................................................................116
4
, Nitrillen ...................................................................................................................................................117
Moleculen met meervoudige bindingen & functionele groepen .........................................................................117
De carbonylgroep ...........................................................................................................................................117
Fysische eigenschappen ..................................................................................................................................118
Kookpunt .................................................................................................................................................118
Oplosbaarheid ...........................................................................................................................................118
Biologische functies van carbonylverbindingen ..................................................................................................119
Vetzuren ...................................................................................................................................................119
Zepen ......................................................................................................................................................120
Wassen.....................................................................................................................................................121
Vetten & oliën ...........................................................................................................................................122
Intermezzo................................................................................................................................................122
Fosfoglyceriden & sfingolipiden ..................................................................................................................123
Hoofdstuk 9: Organische reacties (deel 2) ...............................................................................................................................125
Inleiding .......................................................................................................................................................125
Keto-enol-tautomerie ......................................................................................................................................125
Nucleofiele addities aan carbonylgroepen ..........................................................................................................127
Additie van water ......................................................................................................................................128
Additie van alcoholen.................................................................................................................................129
Additie van stikstofnucleotiden ....................................................................................................................130
Aldolcondensatie ...........................................................................................................................................131
Biologische aldolcondensatie ......................................................................................................................131
Oxidatie- & reductiereacties met carbonylverbindingen .......................................................................................132
Oxidatiereacties.........................................................................................................................................132
Reductiereacties ........................................................................................................................................133
Hoofdstuk 10: Organische reacties (deel 3) .............................................................................................................................134
Omzetting van carbonzuren in zouten ................................................................................................................134
Decarboxylering ............................................................................................................................................134
Deprotonering, decarboxylering & dehydraterig van dicarbonzuren .......................................................................134
Deprotonering ...........................................................................................................................................134
Bereiding van esters .......................................................................................................................................135
Verestering ...............................................................................................................................................135
Methylering ..............................................................................................................................................136
Hydrolyse van esters .......................................................................................................................................136
Zuurgekatalyseerde hydrolyse .....................................................................................................................136
Verzeping van esters ..................................................................................................................................137
Omestering = Transesterificatie ........................................................................................................................137
Aminolyse van een ester..................................................................................................................................138
Hydrolyse & alcoholyse van amiden .................................................................................................................139
5
, Hydrolyse van nitrillen tot carbonzuren .............................................................................................................140
Claisencondensatie .........................................................................................................................................140
Oxidatie- & reductiereacties met carbonzuren en carbonzuurderivaten ...................................................................141
Oxidatiereacties.........................................................................................................................................141
Reductiereacties ........................................................................................................................................141
Geactiveerde acylverbindingen.........................................................................................................................141
Zuurhalogeniden .......................................................................................................................................142
Zuuranhydriden .........................................................................................................................................143
Thio-esters: De acylactiverende groepen van de natuur ........................................................................................143
Hoofdstuk 11: Polyfunctionele verbindingen ..........................................................................................................................145
Inleiding .......................................................................................................................................................145
Koolhydraten of sacchariden ............................................................................................................................145
Inleiding...................................................................................................................................................145
Classificatie van koolhydraten .....................................................................................................................145
Configuratie van monosacchariden...............................................................................................................146
Configuraties van de aldosen .......................................................................................................................147
Configuraties van de ketosen .......................................................................................................................147
Reacties met monosacchariden ....................................................................................................................148
Cyclische structuur van monosacchariden .....................................................................................................148
Disacchariden ...........................................................................................................................................150
Zoetstoffen ...............................................................................................................................................151
Polysacchariden ........................................................................................................................................152
Andere belangrijke koolhydraten .................................................................................................................153
Aminozuren ..................................................................................................................................................153
Inleiding...................................................................................................................................................153
Eigenschappen ..........................................................................................................................................155
Peptidebinding ..........................................................................................................................................156
Decarboxylering ........................................................................................................................................156
Reactiemechanismen overzicht .................................................................................................................................................158
6
,Hoofdstuk 1: Inleiding
Geschiedenis
Organische chemie → Sinds oudheid:
o Stoffen extraheren uit planten & dieren als geneesmiddel
• Bv. “Aspirine” = Acetylsalicylzuur uit wilgen (salix) → Koortsverlagende,
pijnstillende eigenschappen
o Kleurstoffen extraheren uit planten
• Bv. Indigo uit indigofera tinctoria
Begin 19de eeuw:
o Idee van het vitalisme heerst:
• Levende organismen verschillen fundamenteel van niet-levende organismen,
omdat ze een onstoffelijke levenskracht (“Élan vital”) bevatten.
o Verbindingen worden opgedeeld in 2 groepen:
• Organisch: Afkomstig van levende dieren
• Anorganisch: Afkomstig van minerale oorsprong of niet-levende materie
o Overtuiging: Organische stoffen kunnen niet uit anorganische stoffen worden bereid.
1828:
o Friedrich Wöhler: Synthetiseerde ureum (organisch want metaboliet uit urine
zoogdieren) uit anorganische verbindingen
Synthese van ureum uit zilvercyanaat en ammoniumchloride
Heden:
o Organische (natuur)producten worden standaard gesynthetiseerd in laboratorium
Waarom organische chemie?
Organische chemie = Studie koolstofhoudende verbindingen
Koolstof:
o Midden 2de rij PSE
• Geeft noch ontvangt elektronen → Deelt
• Stabiele covalente bindingen (met andere koolstofatomen & meeste andere atomen)
o Basisbouwsteen leven op aarde
7
, o Kennis belangrijk in veel wetenschappelijke velden:
• Biochemie
• Medicinale chemie = Studie van ontwikkeling van medicijnen
• Farmacologie = Studie van effect medicijn op patiënt en omgekeerd
o Belangrijk in verschillende industriële velden:
• Voedingsindustrie:
▪ Bereiding bier
▪ Pesticiden & herbiciden
▪ Kleurstoffen
▪ Bewaarmiddelen
• Textielindustrie
▪ Brandvertragende en/of waterafstotende kledij
▪ kleurstoffen
• Materiaalindustrie
▪ Kunststoffen
▪ Ontwikkeling zelfherstellende materialen
▪ Voedselverpakkingen
• Farmacie
▪ Bereiding geneesmiddelen & behandelingen
▪ Modificeren cellen met fluorescerende kleurstoffen & actieve
farmaceutische stoffen
Cruciale informatie
Typen bindingen
Ionaire binding
o Elektronenoverdracht van ene naar andere atoom
• Metalen → Neiging om elektronen af te staan
• Niet-metalen → Neiging om elektronen op te nemen
o Resultaat elektrostatische aantrekking tss. ionen van tegengestelde lading
o Specifiek kristalrooster
o Bv. Natriumchloride
8
, Covalente binding
o Valentie-elektronen gemeenschappelijk stellen
o (Meestal 2) Elektronen delen → Gemeenschappelijk elektronenpaar
o Apolair of polair
Apolaire covalente binding
o Gelijke ladingsverdeling t.g.v. gelijke elektronegativiteit
o Bv. Waterstofgas (H2) en chloorgas (Cl2)
Polaire covalente binding
o Ongelijke ladingsverdeling t.g.v. verschillende elektronegativiteiten
o Meest elektronegatieve → Grootste ladingsdichtheid
• PSE → Hoe dichter bij fluor (rechtsboven), hoe hoger EN
o Partieel positieve & partieel negatieve lading → Heeft dipool
• Grootte: Aangeduid met dipoolmoment (µ)
• Richting: Aangeduid met pijltje (+ → -)
▪ 1 covalente binding: Dipoolmoment = Dipoolmoment binding
▪ Meerdere bindingen: Dipoolmoment = Dipoolmoment afh. van
dipoolmomenten ALLE bindingen + Geometrie (Vectoriële som)
➢ Dipoolmoment = 0 (Heffen elkaar op) → Molecule =
Apolair, bindingen polair
o Bv. Water (H2O), ammoniak (NH3), zoutzuur (HCl)
Algemeen:
o Ionaire binding ↔ Polair covalente binding ↔ Apolair covalente binding
• Hoe groter verschil in elektronegativiteit, hoe groter “ionaire karakter”
• Hoe kleiner verschil in elektronegativiteit, hoe groter “covalente karakter”
o Netto dipoolmoment molecule weten → Ruimtelijke structuur nodig!
Ruimtelijke structuur
Lewisstructuur
1. Zoek het totale aantal valentie-elektronen voor alle atomen in de molecule.
• Voeg 1 elektron toe voor elke negatieve lading
• Trek 1 elektron af voor elke positieve lading
9
