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Samenvatting Organische chemie

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De nomenclatuur van de organische moleculen wordt behandeld. Daarnaast komen de fysische eigenschappen beperkt aan bod. Een belangrijk pakket vormt de chemische reacties die plaatsvinden in de organische chemie. De link wordt gelegd naar de cursus biochemie. Volgende hoofdstukken worden besproke...

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  • January 22, 2022
  • 133
  • 2021/2022
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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


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, 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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