MolScript-galerij: reactiemechanismen geschreven als tekst

Elk mechanisme hieronder bestaat uit een paar regels MolScript en de tekening die MolDraw ervan maakt. Het zijn dezelfde scripts die MolDraw bij elke wijziging test: elk moet getekend worden met elke gebogen pijl volgens de tekenregels geplaatst, en de pijlen moeten elektron voor elektron de producten opleveren die erna geschreven staan. Een mechanisme staat hier alleen als het slaagt.

Kopieer een script naar het tabblad MolScript van het paneel Templates in MolDraw, of vraag de AI-assistent om een mechanisme, en bewerk het vanaf daar.

SN2

title: SN2 of bromomethane
[OH-:1] "hydroxide" + [CH3:2][Br:3] "bromomethane" ->[SN2][acetone] CO "methanol" + [Br-]
move :1 -> 1..2
move 2-3 -> 3

SN1

title: SN1 of tert-butyl bromide
C[C:1](C)(C)[Br:2] ->[slow] C[C+:3](C)C + [Br-]
move 1-2 -> 2
-> C[C+:4](C)C + [OH2:5]
move :5 -> 5..4
->[fast] CC(C)(C)[OH2+]

E2

title: E2 elimination
[OH-:1] + [H:4][CH2:2][CH:3](C)[Br:5] ->[E2] C=CC + O + [Br-]
move :1 -> 1..4; 4-2 -> 2-3; 3-5 -> 5

Cyaanhydrine

title: Cyanide addition to a carbonyl
[C-:1]#N + C[CH:2]=[O:3] -> CC([O-])C#N
move :1 -> 1..2
move 2-3 -> 3

Hydridereductie

title: NaBH4 reduction of acetone
[H:1][BH3-:2] + C[C:3](C)=[O:4] ->[H⁻ transfer] CC([O-])C
move 1-2 -> 1..3
move 3-4 -> 4

Esterhydrolyse (additiestap)

[OH-:1] + C[C:2](=[O:3])OC ->[addition] CC([O-])(O)OC
move :1 -> 1..2
move 2-3 -> 3

Ineenstorting van het tetraëdrische intermediair

C[C:1]([O-:2])(O)[O:3]C ->[elimination] CC(=O)O + [O-]C
move :2 -> 2-1
move 1-3 -> 3

Aldoladditie

title: Aldol addition
[CH2-:1]C(C)=O "enolate" + C[CH:2]=[O:3] "acetaldehyde" -> CC([O-])CC(C)=O
move :1 -> 1..2
move 2-3 -> 3

Michael-additie

title: Michael addition
[CH2-:1]C(C)=O + [CH2:2]=[CH:3][C:4](C)=[O:5] ->[1,4-addition] CC(=O)CCC=C(C)[O-]
move :1 -> 1..2; 2-3 -> 3-4; 4-5 -> 5

Resonantie van het enolaat

[CH2-:1][C:2](C)=[O:3] <-> C=C(C)[O-]
move :1 -> 1-2
move 2-3 -> 3

Resonantie van de nitrogroep

C[N+:1](=[O:2])[O-:3] <-> C[N+]([O-])=O
move :3 -> 3-1
move 1-2 -> 2

Resonantie van het allylkation

[CH2:1]=[CH:2][CH2+:3] <-> [CH2+]C=C
move 1-2 -> 2-3

Protonering van een carbonylgroep

[O:1]=C(C)C + [H:3][OH2+:4] ->[H⁺ transfer] [OH+]=C(C)C + O
move :1 -> 1..3
move 3-4 -> 4

Hemiacetaalstap

C[CH:1]=[OH+:2] + [OH:3]C ->[addition] CC(O)[OH+]C
move :3 -> 3..1
move 1-2 -> 2

Ringopening van een epoxide

[OH-:1] + C[CH:2]1[O:3]C1 ->[SN2] CC(O)C[O-]
move :1 -> 1..2
move 2-3 -> 3

Bromering van een alkeen

title: Bromination of ethene
[CH2:1]=[CH2:2] + [Br:3][Br:4] -> C1C[Br+]1 + [Br-]
move 1-2 -> 3; :3 -> 3..2
move 3-4 -> 4

Friedel-Craftsaanval

[CH:1]1=[CH:2]C=CC=C1 + C[C+:3]=O ->[SEAr] CC(=O)C1C=CC=C[CH+]1
move 1-2 -> 2..3

Deprotonering van het areniumion

CC(=O)[C:1]1([H:2])C=CC=C[CH+:3]1 + [Cl-:4] ->[−H⁺] CC(=O)c1ccccc1 + Cl
move :4 -> 4..2; 2-1 -> 1-3

Diels-Alder

title: Diels–Alder
[CH2:1]=[CH:2][CH:3]=[CH2:4] + [CH2:5]=[CH2:6] ->[Δ] C1CC=CCC1
move 1-2 -> 2-3; 3-4 -> 4..5; 5-6 -> 6..1

Homolyse van broom

[Br:1][Br:2] ->[hν] [Br] + [Br]
move 1-2 ~> 1; 1-2 ~> 2

Radicaaladditie

title: Radical addition of Br• to propene
[Br:1] + [CH2:2]=[CH:3]C -> BrC[CH]C
move 1 ~> 1..2
move 2-3 ~> 1..2
move 2-3 ~> 3

Resonantie van het carboxylaat

C[C:1](=[O:2])[O-:3] <-> CC([O-])=O
move :3 -> 3-1
move 1-2 -> 2

SN2 via de overgangstoestand

title: SN2 through its transition state
per-row: 5
[OH-:1] + [CH3:2][Br:3] {δ+=2 δ-=3} -> [OH]~C([H])([H])([H])~[Br] {ts} -> CO + [Br-]
move :1 -> 1..2; 2-3 -> 3

Nucleofiele additie met R-groepen

title: Nucleophile adds to a ketone
[Nu-:1] + [R1][C:2](=[O:3])[R2] -> [Nu]C([R1])([R2])[O-]
move :1 -> 1..2; 2-3 -> 3

E2 met een benoemd waterstofatoom

title: E2 elimination (hN names the hydrogen)
let base = [OH-:1] "hydroxide"
$base + [CH3:2][CH:3](C)[Br:5] ->[E2] C=CC + O + [Br-]
move :1 -> 1..h2; h2-2 -> 2-3; 3-5 -> 5

Friedel-Craftsacylering met een reagensstructuur

title: Friedel–Crafts acylation
c1ccccc1 ->[{CC(=O)Cl}][AlCl3] CC(=O)c1ccccc1 + Cl

Katalytische cyclus van de Suzukikoppeling

title: Suzuki coupling: catalytic cycle
layout: cycle
[Pd] "Pd(0)" ->[oxidative addition][+ ArBr] Br[Pd][Ar]
->[transmetalation][+ PhB(OH)2] [Ph][Pd][Ar]
->[reductive elimination][− Ar–Ph] [Pd]

Iminevorming: additie van het amine

title: Imine formation, step 1
C[CH:1]=[O:2] + [NH2:3]C ->[addition] CC([O-])[NH2+]C
move :3 -> 3..1; 1-2 -> 2

Vorming van het oxocarbeniumion (acetaal)

title: Acetal formation: loss of water
C[CH:1]([O:2]C)[OH2+:3] -> C[CH]=[O+]C + O
move :2 -> 2-1; 1-3 -> 3

E1-deprotonering

title: E1: water removes a proton
C[C+:1](C)[CH3:2] + [OH2:3] -> C=C(C)C + [OH3+]
move :3 -> 3..h2; h2-2 -> 2-1

Additiestap van de Claisencondensatie

title: Claisen condensation: enolate addition
[CH2-:1]C(=O)OC + C[C:2](=[O:3])OC -> COC(=O)CC(C)([O-])OC
move :1 -> 1..2; 2-3 -> 3

Vorming van een halohydrine

title: Water opens a bromonium ion
[CH2:2]1[CH2:3][Br+:1]1 + [OH2:4] -> [OH2+]CCBr
move :4 -> 4..2; 2-1 -> 1

Propagatie bij radicaalchlorering

title: Chlorination of methane: propagation
[Cl:1] + [H:2][CH3:3] ->[hν] Cl + [CH3]
move 1 ~> 1..2; 2-3 ~> 1..2; 2-3 ~> 3

Koppeling van methylradicalen

title: Radical termination
[CH3:1] + [CH3:2] -> CC
move 1 ~> 1..2; 2 ~> 1..2

Deprotonering van een carbonzuur

title: Hydroxide deprotonates acetic acid
[OH-:1] + CC(=O)[OH:2] -> CC(=O)[O-] + O
move :1 -> 1..h2; h2-2 -> 2

Resonantie van het amide

C[C:1](=[O:2])[NH2:3] <-> CC([O-])=[NH2+]
move :3 -> 3-1; 1-2 -> 2

SN1 zonder mapnummers

title: SN1 with element ends, numbered, snake rows
number: both
wrap: snake
per-row: 3
CC(C)(C)Br ->[slow] C[C+](C)C + [Br-]
move C-Br -> Br
-> C[C+](C)C + O
move :O -> O..C+
->[fast] CC(C)(C)[OH2+]

SN2 met markering

title: SN2 with the reacting atoms highlighted
[OH-:1] {highlight=1:blue} + [CH3:2][Br:3] {highlight=2/2-3:red} -> CO + [Br-]
move :1 -> 1..2; 2-3 -> 3

Pd-cyclus met oxidatietoestanden

title: Cross-coupling cycle with oxidation states
layout: cycle
[Pd:1] {ox=1:0} ->[oxidative addition][+ ArX] [X][Pd:2][Ar] {ox=2:II}
->[transmetalation][+ R–M] [R][Pd:3][Ar] {ox=3:II}
->[reductive elimination][− Ar–R] [Pd:1]

Grignardadditie (ionenpaar)

title: Grignard addition to a ketone
[CH3:1][Mg:2]Br + C[C:3](C)=[O:4] -> CC(C)(C)[O-] + [Mg+]Br
move 1-2 -> 1..3; 3-4 -> 4

Protonering van een alkoxide

title: Work-up: the alkoxide is protonated
CC(C)(C)[O-:1] + [H:2][OH2+:3] -> CC(C)(C)O + O
move :1 -> 1..2; 2-3 -> 3