SAMENVATTING ORGANISCHE CHEMIE
INHOUD
Chemische reactiviteit en stabiliteit ........................................................................................................................ 8
Arrhenius ............................................................................................................................................................. 8
Brondsted en Lowry ............................................................................................................................................ 9
Lewis.................................................................................................................................................................... 9
Elektrofiel – Neutrofiel ...................................................................................................................................... 10
Reactieve koolstofintermediaren ..................................................................................................................... 11
Mesomerie (uitleggen op examen) ................................................................................................................... 12
Kenmerken van mesomere structuren (niet van buiten leren, wel toepassen) ........................................... 13
Voorwaarden mesomerie ............................................................................................................................. 13
Alkanen ................................................................................................................................................................. 14
Nomenclatuur ................................................................................................................................................... 14
Te volgen systeem ......................................................................................................................................... 14
Isomeren ........................................................................................................................................................... 17
Isomeren heptaan (9) .................................................................................................................................... 17
Bouw van alkanen ............................................................................................................................................. 17
CH4 – methaan .............................................................................................................................................. 17
Conformaties van alkanen ................................................................................................................................ 18
Energiediagram rotatie rond C – C in ethaan (examen bespreek) ................................................................ 19
Butaan ........................................................................................................................................................... 19
Fysische eigenschappen .................................................................................................................................... 20
Reacties met alkanen ........................................................................................................................................ 20
Chlorering van methaan (examen).................................................................................................................... 20
Reactie gebeurt in 3 stappen ........................................................................................................................ 20
Stap 1: Initatie: Cl2 breken............................................................................................................................. 21
Stap 2: Propagatie ......................................................................................................................................... 21
Stap 3: Terminatie ......................................................................................................................................... 22
Chlorering van methaan (samengevat) ......................................................................................................... 22
Chlorering van hogere alkanen ......................................................................................................................... 22
Ethaan ........................................................................................................................................................... 22
Classificatie .................................................................................................................................................... 23
Biologische eigenschappen alkanen.................................................................................................................. 24
Cycloalkanen ......................................................................................................................................................... 25
Heterocyclische moleculen (Van buiten leren) ............................................................................................. 26
1
, Cycloalkylgroepen – cyclopropyl ....................................................................................................................... 26
Geometrische isomerie ..................................................................................................................................... 27
Vorm en eigenschappen cyclopropaan ............................................................................................................. 27
Vorm en eigenschappen cylobutaan ................................................................................................................. 28
Vorm en eigenschappen cyclopentaan ............................................................................................................. 28
Cyclohexaan ...................................................................................................................................................... 29
Menthol en isomenthol gunstigst, Waarom? ............................................................................................... 30
Polycyclische verbindingen ............................................................................................................................... 31
Alkenen en Alkynen .............................................................................................................................................. 32
Alkenen ......................................................................................................................................................... 32
Bouw van alkenen – geometrische isomerie .................................................................................................... 33
Chemie van het zien ...................................................................................................................................... 33
Nomenclatuur ................................................................................................................................................... 34
Nomenclatuur – oefeningen ......................................................................................................................... 34
E, Z – nomenclatuur ...................................................................................................................................... 35
Isomeren C4H8 ............................................................................................................................................... 35
Stabiliteit ........................................................................................................................................................... 36
Reacties van alkenen ......................................................................................................................................... 38
Hydrogenering van alkenen – additie van H2 ............................................................................................... 38
Voorbeeld hydrogenering – elektrofiele additie van Zuur HCl ..................................................................... 39
Additie van zuren .............................................................................................................................................. 40
Verklaring regel van Markovnikov ................................................................................................................ 41
Voorbeeld van additie van zuren .................................................................................................................. 41
additie van zuren energiediagram (Kunnen uitleggen examen) ................................................................... 42
Dimerisatie van alkenen .................................................................................................................................... 43
Oefening: reactie van 1 penteen in zuurmilieu ............................................................................................. 44
Omleggingsreacties van carbokation ................................................................................................................ 45
Additie van halogenen ...................................................................................................................................... 46
Oxidatie van alkenen ......................................................................................................................................... 48
Epoxidatie...................................................................................................................................................... 48
Vorming van vicinale alcoholen .................................................................................................................... 49
Ozonolyse ...................................................................................................................................................... 49
Syn – en anti – additie ....................................................................................................................................... 50
Reacties van C – atoom van dubbele binding ............................................................................................... 51
Alkynen ................................................................................................................................................................. 53
Hydrogenering van alkenen .............................................................................................................................. 53
Elektrofiele additie van alkynen ........................................................................................................................ 54
2
, Zuurtegraad van alkynen .................................................................................................................................. 55
Dienen en polymeren ............................................................................................................................................ 55
Dienen ............................................................................................................................................................... 55
Additiereacties van butadieen .......................................................................................................................... 56
Elektrofiele additie ........................................................................................................................................ 56
Diels alder reactie ......................................................................................................................................... 56
Reactie van butadieen en maleinezuuranhydride ........................................................................................ 57
Organochloor – insecticiden ......................................................................................................................... 57
Polymeren ......................................................................................................................................................... 58
Polymeren ..................................................................................................................................................... 59
Structuur en eigenschappen polymeren ....................................................................................................... 60
Oriëntatie ketens .......................................................................................................................................... 60
Fysische eigenschappen → 3 types van polymeren ...................................................................................... 60
Terpenen en steroïden .......................................................................................................................................... 61
Belang mono sesqui en diterpenen .............................................................................................................. 62
Carotenoïden ................................................................................................................................................ 62
Steroïden ....................................................................................................................................................... 62
Emulsie van vetten ........................................................................................................................................ 63
Planten en insectensterioden (1 voorbeeld kennen examen) ...................................................................... 63
Geurstoffen en communicatie ...................................................................................................................... 63
Aromaten .............................................................................................................................................................. 64
Benzeen en aromaticiteit .................................................................................................................................. 64
Benzeen ......................................................................................................................................................... 64
Nomenclatuur ................................................................................................................................................... 65
Nomenclatuur – plaats .................................................................................................................................. 65
Benzeen als substituent ................................................................................................................................ 65
Nomenclatuur ............................................................................................................................................... 66
Fenolen en anilinen ............................................................................................................................................... 66
Nomenclatuur ................................................................................................................................................... 66
Nomenclatuur – oefeningen ......................................................................................................................... 67
Stereochemie ........................................................................................................................................................ 67
Symmetrie en enantiomeren ............................................................................................................................ 68
Configuratie en enantiomeren .......................................................................................................................... 69
R – S nomenclatuur ....................................................................................................................................... 69
Eigenschappen enantiomeren .......................................................................................................................... 70
Diastereomeren en mesoverbindingen ............................................................................................................ 70
Diastereomeren eigenschappen ................................................................................................................... 70
3
,Halogeenalkanen .................................................................................................................................................. 71
Voorkomen........................................................................................................................................................ 71
Nomenclatuur ................................................................................................................................................... 72
Triviale namen ............................................................................................................................................... 72
Nomenclatuur – oefeningen halogeenalkanen ............................................................................................. 73
Fysische eigenschappen – Halogeenalkanen .................................................................................................... 73
Reacties met halogeenalkanen ......................................................................................................................... 74
Nucleofiele substitutie .................................................................................................................................. 74
Vormen Nucleofiele substitutiereacties ............................................................................................................ 75
Wanneer welke reactie? ............................................................................................................................... 75
Sn1 – mechanisme – 2 stappen......................................................................................................................... 76
Stap 1 ............................................................................................................................................................ 76
Stap 2 ............................................................................................................................................................ 76
Snelheid Sn1 – mechanisme.......................................................................................................................... 76
Energiediagram Sn1 – mechanisme .............................................................................................................. 77
Sn2 – mechanisme – 1 stap ............................................................................................................................... 78
Voorbeeld Sn2 – mechanisme....................................................................................................................... 78
Snelheid Sn2 – mechanisme.............................................................................................................................. 78
Energiediagram Sn2 – mechanisme .............................................................................................................. 79
Stereochemie van nucleofiele substitutie ......................................................................................................... 79
Factoren die reactiemechanisme (Sn1) van nucleofiele substitutie bepalen ................................................... 80
Structuur halogeenalkaan ............................................................................................................................. 80
Aard oplosmiddel .......................................................................................................................................... 81
Factoren die reactiemechanisme (Sn2) van nucleofiele substitutie bepalen ................................................... 82
Nucleofielsterkte en basesterkte ...................................................................................................................... 82
Aanwezigheid van grote groepen ................................................................................................................. 83
Oplosmiddel .................................................................................................................................................. 84
Nucleofiele substitutie in biologische systemen ............................................................................................... 84
Mosterdgas ................................................................................................................................................... 85
Eliminatiereactie ............................................................................................................................................... 85
E1 – mechanisme .......................................................................................................................................... 86
E2 – mechanisme .............................................................................................................................................. 87
E2 – eliminatie – stereospecifiek................................................................................................................... 87
Alcoholen en thiolen ............................................................................................................................................. 88
Alcoholen .......................................................................................................................................................... 88
Thiolen .............................................................................................................................................................. 88
Nomenclatuur – alcoholen ................................................................................................................................ 88
4
, Nomenclatuur – thiolen .................................................................................................................................... 90
Nomenclatuur – oefeningen ......................................................................................................................... 90
Fysische eigenschappen .................................................................................................................................... 90
Ethanol .......................................................................................................................................................... 91
Reacties van alcoholen ...................................................................................................................................... 92
Zure en basische eigenschappen .................................................................................................................. 92
Nucleofiele eigenschappen met alcoholen en thiolen ...................................................................................... 93
Reacties met halogeenalkanen ..................................................................................................................... 93
Substitutiereacties met alcoholen ................................................................................................................ 94
Eliminatiereacties .......................................................................................................................................... 95
Oxidatie van alcoholen .................................................................................................................................. 96
Ethers, epoxiden, sulfiden ..................................................................................................................................... 96
Ethers ................................................................................................................................................................ 96
Diethylether .................................................................................................................................................. 97
Epoxide .......................................................................................................................................................... 97
SUFLIDEN ....................................................................................................................................................... 97
Nomenclatuur ................................................................................................................................................... 98
Nomenclatuur – oefeningen ......................................................................................................................... 98
Nomenclatuur – Isomeren ............................................................................................................................ 99
FYSISCHE EIGENSCHAPPEN ETHERS .................................................................................................................. 99
Diethylether ...................................................................................................................................................... 99
Chemische eigenschappen van ethers en sulfiden ......................................................................................... 100
Epoxiden.......................................................................................................................................................... 100
Aminen en alkaloïden ......................................................................................................................................... 101
Aminen ............................................................................................................................................................ 101
Indeling amines op basis van structuur....................................................................................................... 101
Nomenclatuur - aminen .................................................................................................................................. 102
Arylamine .................................................................................................................................................... 102
Acyclische aminen ....................................................................................................................................... 103
Nomenclatuur – aminen – oefeningen ........................................................................................................... 104
Voorkomen van amines (aminozuren + 1 ander voorbeeld kennen) .............................................................. 104
Histamine .................................................................................................................................................... 105
Fysische eigenschappen aminen ..................................................................................................................... 105
Aldehyden en ketonen ........................................................................................................................................ 106
Nomenclatuur – aldehyden............................................................................................................................. 106
Nomenclatuur – ketonen ................................................................................................................................ 107
Dion of trion ................................................................................................................................................ 107
5
, Te kennen triviale namen............................................................................................................................ 108
Nomenclatuur – oefeningen ........................................................................................................................... 108
Fysische eigenschappen .................................................................................................................................. 109
Reacties van aldehyden en ketonen ................................................................................................................... 109
Nucleofiele additie van de carbonylgroep ...................................................................................................... 110
Neutraal milieu ............................................................................................................................................ 110
Zuur milieu .................................................................................................................................................. 110
Nucleofiele additie onder basische omstandigheden ..................................................................................... 111
Additie van water ........................................................................................................................................ 111
Additie van alcoholen...................................................................................................................................... 112
Vorming van halfacetalen ........................................................................................................................... 112
Additie van waterstofcyanide ......................................................................................................................... 113
Additie van organometaalverbindingen ......................................................................................................... 113
Additie van metaalhybriden – Reductie van de carbonylgroep ...................................................................... 114
Reductie met NaBH4 of LiAIH4 ..................................................................................................................... 114
Reductie in biologische systemen ............................................................................................................... 115
Additie van waterstof .................................................................................................................................. 115
Nucleofiele additie onder zure omstandigheden ............................................................................................ 116
Vorming van acetalen ................................................................................................................................. 116
Carbonzuren ........................................................................................................................................................ 117
Belang carbonzuren .................................................................................................................................... 117
Nomenclatuur ................................................................................................................................................. 117
Nomenclatuur – oefeningen ........................................................................................................................... 120
Voorkomen carbonzuren ................................................................................................................................ 121
Fysische eigenschappen .................................................................................................................................. 121
Synthese van carbonzuren .............................................................................................................................. 122
Primaire alcoholen ...................................................................................................................................... 122
Grigard / organometaalverbinding ............................................................................................................. 122
Zuurtegraad van carbonzuren ......................................................................................................................... 122
Vorming carbonzuurderivaten ........................................................................................................................ 123
Vorming zuurchloriden ............................................................................................................................... 123
Vorming zuuranhydriden ............................................................................................................................ 123
Vorming van esters ..................................................................................................................................... 124
Reductie van carbonzuren .............................................................................................................................. 124
Decarboxylering van carbonzuren .................................................................................................................. 124
Derivaten van carbonzuren ................................................................................................................................. 125
Nomenclatuur ................................................................................................................................................. 125
6
, Zuurchloriden .............................................................................................................................................. 125
Anhydriden .................................................................................................................................................. 125
Esters ........................................................................................................................................................... 126
Amiden ........................................................................................................................................................ 126
Namen van structuurfragmenten ................................................................................................................... 127
Nomenclatuur – oefeningen ........................................................................................................................... 127
Additie – eliminatiereactie .............................................................................................................................. 128
Reactiviteit carbonzuurderivaten ................................................................................................................ 128
Omzettingsmogelijkheden .......................................................................................................................... 129
Zuurchloriden .................................................................................................................................................. 130
Esters ............................................................................................................................................................... 130
Synthese van esters..................................................................................................................................... 130
Hydrolyse van esters ................................................................................................................................... 131
Omestering .................................................................................................................................................. 131
Aminolyse van esters .................................................................................................................................. 132
Reactie van esters met organometaalverbindingen ................................................................................... 132
Nitrillen ........................................................................................................................................................... 133
Nomenclatuur – oefeningen ....................................................................................................................... 133
7
,CHEMISCHE REACTIVITEIT EN STABILITEIT
ARRHENIUS
• Zuur in H2O → Levert H+
• Base in H2O → Levert OH-
• Zuursterkte → protonenoverdracht in H2O
(EVENWICHTSCONSTANTE)
➔ Zuurconstante Ka
o Grootte → maat voor de zuursterkte
▪ Sterkzuur = Hoge Ka
▪ Zwak zuur = Lage Ka
o Zuursterkte → pKa – waarde
▪ pKa = -log Ka
o pKa laag → sterkzuur
o pKa hoog → zwakzuur
8
,BRONDSTED EN LOWRY
• zuur → Protondonor
• base → Protonacceptor
o in H2O als in niet H2O
Amfoteer = Kan zowel als een base, als een zuur gaan reageren
LEWIS
• zuur → elektronenpaar acceptor
• base → elektronenpaar donor
ZUUR BASE
Arrhenius Levert H+ Levert OH-
Brondsted en Lowry Protondonor Protonacceptor
Lewis elektronenpaar acceptor elektronenpaar donor
ELEKTROFIEL NEUTROFIEL
9
, ELEKTROFIEL – NEUTROFIEL
Elektrofiel Neutrofiel
= een deeltje dat makkelijk elektronen opneemt = een deeltje dat makkelijk elektronen deelt
Lewis – zuren Lewis – basen
Vb. H+ Vb. Cl-
Veel negatief
CH3
CH3
Methylgroep
➔ Sterkste zuur: H2O
10
INHOUD
Chemische reactiviteit en stabiliteit ........................................................................................................................ 8
Arrhenius ............................................................................................................................................................. 8
Brondsted en Lowry ............................................................................................................................................ 9
Lewis.................................................................................................................................................................... 9
Elektrofiel – Neutrofiel ...................................................................................................................................... 10
Reactieve koolstofintermediaren ..................................................................................................................... 11
Mesomerie (uitleggen op examen) ................................................................................................................... 12
Kenmerken van mesomere structuren (niet van buiten leren, wel toepassen) ........................................... 13
Voorwaarden mesomerie ............................................................................................................................. 13
Alkanen ................................................................................................................................................................. 14
Nomenclatuur ................................................................................................................................................... 14
Te volgen systeem ......................................................................................................................................... 14
Isomeren ........................................................................................................................................................... 17
Isomeren heptaan (9) .................................................................................................................................... 17
Bouw van alkanen ............................................................................................................................................. 17
CH4 – methaan .............................................................................................................................................. 17
Conformaties van alkanen ................................................................................................................................ 18
Energiediagram rotatie rond C – C in ethaan (examen bespreek) ................................................................ 19
Butaan ........................................................................................................................................................... 19
Fysische eigenschappen .................................................................................................................................... 20
Reacties met alkanen ........................................................................................................................................ 20
Chlorering van methaan (examen).................................................................................................................... 20
Reactie gebeurt in 3 stappen ........................................................................................................................ 20
Stap 1: Initatie: Cl2 breken............................................................................................................................. 21
Stap 2: Propagatie ......................................................................................................................................... 21
Stap 3: Terminatie ......................................................................................................................................... 22
Chlorering van methaan (samengevat) ......................................................................................................... 22
Chlorering van hogere alkanen ......................................................................................................................... 22
Ethaan ........................................................................................................................................................... 22
Classificatie .................................................................................................................................................... 23
Biologische eigenschappen alkanen.................................................................................................................. 24
Cycloalkanen ......................................................................................................................................................... 25
Heterocyclische moleculen (Van buiten leren) ............................................................................................. 26
1
, Cycloalkylgroepen – cyclopropyl ....................................................................................................................... 26
Geometrische isomerie ..................................................................................................................................... 27
Vorm en eigenschappen cyclopropaan ............................................................................................................. 27
Vorm en eigenschappen cylobutaan ................................................................................................................. 28
Vorm en eigenschappen cyclopentaan ............................................................................................................. 28
Cyclohexaan ...................................................................................................................................................... 29
Menthol en isomenthol gunstigst, Waarom? ............................................................................................... 30
Polycyclische verbindingen ............................................................................................................................... 31
Alkenen en Alkynen .............................................................................................................................................. 32
Alkenen ......................................................................................................................................................... 32
Bouw van alkenen – geometrische isomerie .................................................................................................... 33
Chemie van het zien ...................................................................................................................................... 33
Nomenclatuur ................................................................................................................................................... 34
Nomenclatuur – oefeningen ......................................................................................................................... 34
E, Z – nomenclatuur ...................................................................................................................................... 35
Isomeren C4H8 ............................................................................................................................................... 35
Stabiliteit ........................................................................................................................................................... 36
Reacties van alkenen ......................................................................................................................................... 38
Hydrogenering van alkenen – additie van H2 ............................................................................................... 38
Voorbeeld hydrogenering – elektrofiele additie van Zuur HCl ..................................................................... 39
Additie van zuren .............................................................................................................................................. 40
Verklaring regel van Markovnikov ................................................................................................................ 41
Voorbeeld van additie van zuren .................................................................................................................. 41
additie van zuren energiediagram (Kunnen uitleggen examen) ................................................................... 42
Dimerisatie van alkenen .................................................................................................................................... 43
Oefening: reactie van 1 penteen in zuurmilieu ............................................................................................. 44
Omleggingsreacties van carbokation ................................................................................................................ 45
Additie van halogenen ...................................................................................................................................... 46
Oxidatie van alkenen ......................................................................................................................................... 48
Epoxidatie...................................................................................................................................................... 48
Vorming van vicinale alcoholen .................................................................................................................... 49
Ozonolyse ...................................................................................................................................................... 49
Syn – en anti – additie ....................................................................................................................................... 50
Reacties van C – atoom van dubbele binding ............................................................................................... 51
Alkynen ................................................................................................................................................................. 53
Hydrogenering van alkenen .............................................................................................................................. 53
Elektrofiele additie van alkynen ........................................................................................................................ 54
2
, Zuurtegraad van alkynen .................................................................................................................................. 55
Dienen en polymeren ............................................................................................................................................ 55
Dienen ............................................................................................................................................................... 55
Additiereacties van butadieen .......................................................................................................................... 56
Elektrofiele additie ........................................................................................................................................ 56
Diels alder reactie ......................................................................................................................................... 56
Reactie van butadieen en maleinezuuranhydride ........................................................................................ 57
Organochloor – insecticiden ......................................................................................................................... 57
Polymeren ......................................................................................................................................................... 58
Polymeren ..................................................................................................................................................... 59
Structuur en eigenschappen polymeren ....................................................................................................... 60
Oriëntatie ketens .......................................................................................................................................... 60
Fysische eigenschappen → 3 types van polymeren ...................................................................................... 60
Terpenen en steroïden .......................................................................................................................................... 61
Belang mono sesqui en diterpenen .............................................................................................................. 62
Carotenoïden ................................................................................................................................................ 62
Steroïden ....................................................................................................................................................... 62
Emulsie van vetten ........................................................................................................................................ 63
Planten en insectensterioden (1 voorbeeld kennen examen) ...................................................................... 63
Geurstoffen en communicatie ...................................................................................................................... 63
Aromaten .............................................................................................................................................................. 64
Benzeen en aromaticiteit .................................................................................................................................. 64
Benzeen ......................................................................................................................................................... 64
Nomenclatuur ................................................................................................................................................... 65
Nomenclatuur – plaats .................................................................................................................................. 65
Benzeen als substituent ................................................................................................................................ 65
Nomenclatuur ............................................................................................................................................... 66
Fenolen en anilinen ............................................................................................................................................... 66
Nomenclatuur ................................................................................................................................................... 66
Nomenclatuur – oefeningen ......................................................................................................................... 67
Stereochemie ........................................................................................................................................................ 67
Symmetrie en enantiomeren ............................................................................................................................ 68
Configuratie en enantiomeren .......................................................................................................................... 69
R – S nomenclatuur ....................................................................................................................................... 69
Eigenschappen enantiomeren .......................................................................................................................... 70
Diastereomeren en mesoverbindingen ............................................................................................................ 70
Diastereomeren eigenschappen ................................................................................................................... 70
3
,Halogeenalkanen .................................................................................................................................................. 71
Voorkomen........................................................................................................................................................ 71
Nomenclatuur ................................................................................................................................................... 72
Triviale namen ............................................................................................................................................... 72
Nomenclatuur – oefeningen halogeenalkanen ............................................................................................. 73
Fysische eigenschappen – Halogeenalkanen .................................................................................................... 73
Reacties met halogeenalkanen ......................................................................................................................... 74
Nucleofiele substitutie .................................................................................................................................. 74
Vormen Nucleofiele substitutiereacties ............................................................................................................ 75
Wanneer welke reactie? ............................................................................................................................... 75
Sn1 – mechanisme – 2 stappen......................................................................................................................... 76
Stap 1 ............................................................................................................................................................ 76
Stap 2 ............................................................................................................................................................ 76
Snelheid Sn1 – mechanisme.......................................................................................................................... 76
Energiediagram Sn1 – mechanisme .............................................................................................................. 77
Sn2 – mechanisme – 1 stap ............................................................................................................................... 78
Voorbeeld Sn2 – mechanisme....................................................................................................................... 78
Snelheid Sn2 – mechanisme.............................................................................................................................. 78
Energiediagram Sn2 – mechanisme .............................................................................................................. 79
Stereochemie van nucleofiele substitutie ......................................................................................................... 79
Factoren die reactiemechanisme (Sn1) van nucleofiele substitutie bepalen ................................................... 80
Structuur halogeenalkaan ............................................................................................................................. 80
Aard oplosmiddel .......................................................................................................................................... 81
Factoren die reactiemechanisme (Sn2) van nucleofiele substitutie bepalen ................................................... 82
Nucleofielsterkte en basesterkte ...................................................................................................................... 82
Aanwezigheid van grote groepen ................................................................................................................. 83
Oplosmiddel .................................................................................................................................................. 84
Nucleofiele substitutie in biologische systemen ............................................................................................... 84
Mosterdgas ................................................................................................................................................... 85
Eliminatiereactie ............................................................................................................................................... 85
E1 – mechanisme .......................................................................................................................................... 86
E2 – mechanisme .............................................................................................................................................. 87
E2 – eliminatie – stereospecifiek................................................................................................................... 87
Alcoholen en thiolen ............................................................................................................................................. 88
Alcoholen .......................................................................................................................................................... 88
Thiolen .............................................................................................................................................................. 88
Nomenclatuur – alcoholen ................................................................................................................................ 88
4
, Nomenclatuur – thiolen .................................................................................................................................... 90
Nomenclatuur – oefeningen ......................................................................................................................... 90
Fysische eigenschappen .................................................................................................................................... 90
Ethanol .......................................................................................................................................................... 91
Reacties van alcoholen ...................................................................................................................................... 92
Zure en basische eigenschappen .................................................................................................................. 92
Nucleofiele eigenschappen met alcoholen en thiolen ...................................................................................... 93
Reacties met halogeenalkanen ..................................................................................................................... 93
Substitutiereacties met alcoholen ................................................................................................................ 94
Eliminatiereacties .......................................................................................................................................... 95
Oxidatie van alcoholen .................................................................................................................................. 96
Ethers, epoxiden, sulfiden ..................................................................................................................................... 96
Ethers ................................................................................................................................................................ 96
Diethylether .................................................................................................................................................. 97
Epoxide .......................................................................................................................................................... 97
SUFLIDEN ....................................................................................................................................................... 97
Nomenclatuur ................................................................................................................................................... 98
Nomenclatuur – oefeningen ......................................................................................................................... 98
Nomenclatuur – Isomeren ............................................................................................................................ 99
FYSISCHE EIGENSCHAPPEN ETHERS .................................................................................................................. 99
Diethylether ...................................................................................................................................................... 99
Chemische eigenschappen van ethers en sulfiden ......................................................................................... 100
Epoxiden.......................................................................................................................................................... 100
Aminen en alkaloïden ......................................................................................................................................... 101
Aminen ............................................................................................................................................................ 101
Indeling amines op basis van structuur....................................................................................................... 101
Nomenclatuur - aminen .................................................................................................................................. 102
Arylamine .................................................................................................................................................... 102
Acyclische aminen ....................................................................................................................................... 103
Nomenclatuur – aminen – oefeningen ........................................................................................................... 104
Voorkomen van amines (aminozuren + 1 ander voorbeeld kennen) .............................................................. 104
Histamine .................................................................................................................................................... 105
Fysische eigenschappen aminen ..................................................................................................................... 105
Aldehyden en ketonen ........................................................................................................................................ 106
Nomenclatuur – aldehyden............................................................................................................................. 106
Nomenclatuur – ketonen ................................................................................................................................ 107
Dion of trion ................................................................................................................................................ 107
5
, Te kennen triviale namen............................................................................................................................ 108
Nomenclatuur – oefeningen ........................................................................................................................... 108
Fysische eigenschappen .................................................................................................................................. 109
Reacties van aldehyden en ketonen ................................................................................................................... 109
Nucleofiele additie van de carbonylgroep ...................................................................................................... 110
Neutraal milieu ............................................................................................................................................ 110
Zuur milieu .................................................................................................................................................. 110
Nucleofiele additie onder basische omstandigheden ..................................................................................... 111
Additie van water ........................................................................................................................................ 111
Additie van alcoholen...................................................................................................................................... 112
Vorming van halfacetalen ........................................................................................................................... 112
Additie van waterstofcyanide ......................................................................................................................... 113
Additie van organometaalverbindingen ......................................................................................................... 113
Additie van metaalhybriden – Reductie van de carbonylgroep ...................................................................... 114
Reductie met NaBH4 of LiAIH4 ..................................................................................................................... 114
Reductie in biologische systemen ............................................................................................................... 115
Additie van waterstof .................................................................................................................................. 115
Nucleofiele additie onder zure omstandigheden ............................................................................................ 116
Vorming van acetalen ................................................................................................................................. 116
Carbonzuren ........................................................................................................................................................ 117
Belang carbonzuren .................................................................................................................................... 117
Nomenclatuur ................................................................................................................................................. 117
Nomenclatuur – oefeningen ........................................................................................................................... 120
Voorkomen carbonzuren ................................................................................................................................ 121
Fysische eigenschappen .................................................................................................................................. 121
Synthese van carbonzuren .............................................................................................................................. 122
Primaire alcoholen ...................................................................................................................................... 122
Grigard / organometaalverbinding ............................................................................................................. 122
Zuurtegraad van carbonzuren ......................................................................................................................... 122
Vorming carbonzuurderivaten ........................................................................................................................ 123
Vorming zuurchloriden ............................................................................................................................... 123
Vorming zuuranhydriden ............................................................................................................................ 123
Vorming van esters ..................................................................................................................................... 124
Reductie van carbonzuren .............................................................................................................................. 124
Decarboxylering van carbonzuren .................................................................................................................. 124
Derivaten van carbonzuren ................................................................................................................................. 125
Nomenclatuur ................................................................................................................................................. 125
6
, Zuurchloriden .............................................................................................................................................. 125
Anhydriden .................................................................................................................................................. 125
Esters ........................................................................................................................................................... 126
Amiden ........................................................................................................................................................ 126
Namen van structuurfragmenten ................................................................................................................... 127
Nomenclatuur – oefeningen ........................................................................................................................... 127
Additie – eliminatiereactie .............................................................................................................................. 128
Reactiviteit carbonzuurderivaten ................................................................................................................ 128
Omzettingsmogelijkheden .......................................................................................................................... 129
Zuurchloriden .................................................................................................................................................. 130
Esters ............................................................................................................................................................... 130
Synthese van esters..................................................................................................................................... 130
Hydrolyse van esters ................................................................................................................................... 131
Omestering .................................................................................................................................................. 131
Aminolyse van esters .................................................................................................................................. 132
Reactie van esters met organometaalverbindingen ................................................................................... 132
Nitrillen ........................................................................................................................................................... 133
Nomenclatuur – oefeningen ....................................................................................................................... 133
7
,CHEMISCHE REACTIVITEIT EN STABILITEIT
ARRHENIUS
• Zuur in H2O → Levert H+
• Base in H2O → Levert OH-
• Zuursterkte → protonenoverdracht in H2O
(EVENWICHTSCONSTANTE)
➔ Zuurconstante Ka
o Grootte → maat voor de zuursterkte
▪ Sterkzuur = Hoge Ka
▪ Zwak zuur = Lage Ka
o Zuursterkte → pKa – waarde
▪ pKa = -log Ka
o pKa laag → sterkzuur
o pKa hoog → zwakzuur
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,BRONDSTED EN LOWRY
• zuur → Protondonor
• base → Protonacceptor
o in H2O als in niet H2O
Amfoteer = Kan zowel als een base, als een zuur gaan reageren
LEWIS
• zuur → elektronenpaar acceptor
• base → elektronenpaar donor
ZUUR BASE
Arrhenius Levert H+ Levert OH-
Brondsted en Lowry Protondonor Protonacceptor
Lewis elektronenpaar acceptor elektronenpaar donor
ELEKTROFIEL NEUTROFIEL
9
, ELEKTROFIEL – NEUTROFIEL
Elektrofiel Neutrofiel
= een deeltje dat makkelijk elektronen opneemt = een deeltje dat makkelijk elektronen deelt
Lewis – zuren Lewis – basen
Vb. H+ Vb. Cl-
Veel negatief
CH3
CH3
Methylgroep
➔ Sterkste zuur: H2O
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