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
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
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