Summary

Samenvatting Organische Chemie

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Course
Organische Chemie (V3A547)

Institution
Katholieke Hogeschool VIVES (VIVES)

Book
Inleiding in de bio-organische chemie

Deze samenvatting bevat alle nodige informatie voor het vak Organische chemie binnen de opleiding Biotechnologie Dit document omvat nomenclatuur, reacties, eigenschappen en termen die te kennen zijn voor het examen. Veel succes ;)

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Uploaded on July 9, 2020
Number of pages 133
Written in 2019/2020
Type Summary

biotechnolgie
organische chemie
2020
vives
samenvatting

Book Title:Inleiding in de bio-organische chemie

Author(s):J.F.J. Engbersen, Ae. de Groot

Edition:Unknown
ISBN:9789074134958
Edition:8

Institution
Katholieke Hogeschool VIVES (VIVES)
Education
Agro-en Biotechnologie
Course
Organische Chemie (V3A547)

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1. Summary - Nomenclatuur en reacties organische chemie
2. Summary - Organische chemie
3. Summary - Begrippen organische chemie
4. Summary - Oefeningen organische chemie
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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

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

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