Summary
Samenvatting Organische chemie 2 reactiemechanismen
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Schema reactiemechanismen
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ReactiesAlkanen
+Br2/hv radicalaire additie op meest gesubstitueerde C
Nitroethaan + H2/Pd/c amine
Alkenen
Elektrofiele additie
+ HX + RO3R of Ti(OPr)4/t-BuOOH
o H en X o Epoxide
o Markovnikov + H+/H2O Anti 2x
o Syn en Anti OH
+ HBr/ROOR + H2/Pd/c
o H en Br o Reductie tot alkaan (ook
o Anti-Markovnikov alkaanhalogeniden alkaan)
o Syn en Anti
+ H2O/p-TsOH Oxidatie
o H en OH + NBS of N-Chloorsuccinimide
o Markovnikov o Radicalaire substitutie op
+ 1.BH3/THF en 2.H202, NaOH, OH- allylstelling
o H en OH + Koud KMnO4, OH-, H2O of 1. OsO4
o Anti-Markovnikov en 2. H2O2
o Syn o Vicinal diol
+ Br2 o Syn
o /H2O of HOBr + Warm KMnO4
Br+ en OH o Ringdoorbraak
Markovnikov o 2x keton of carbonzuur
Anti o Eindstandig CO2 +
o /CH2Cl2 carbonzuur
2x Br + O3 (Ozonolyse)
Anti o /Zn, H2O of / (CH3)2S
o /ROH Ringdoorbraak
Br en RO 2x keton/aldehyde
Anti o /H2O2
Ringdoorbraak
2x keton/carbonzuur
HIO4 + vicinaal diol 2x keton/aldehyde + ringdoorbraak
,Alkynen
Elektrofiele additie
+ HX + H2
o Markovnikov o /Pd/c
o Anti Alkaan
o Overmaat dihalogenide o /Lindlar (vergiftigde
(zelfde C) katalysator)
+ HBr/ROOR Alkeen
o Anti-Markovikov Na (of Li)/NaNH3
o Syn en Anti o Trans alkeen
+ H2O/H2SO4, HgSO4
o Markovnikov Oxidatie
+ 1.BH3/THF en 2.H202, NaOH, OH- + Koud KMnO4, OH-, H2O
o Anti-Markovikov o 2x =O
o Syn o Syn
+ Br2 + Warm KMnO4
o /H2O of HOBr o Ringdoorbraak
Br+ en OH o 2x keton/carbonzuur
Markovnikov o Eindstandig CO2 +
Anti carbonzuur
o /CH2Cl2 + O3/H2O
2x Br o Ringdoorbraak
Anti o 2x keton/carbonzuur
o /ROH
Br en RO
Anti
, Alcoholen
Nucleofiele substitutie
1° ROH (SN2) 2° ROH (SN1 en SN2)
o RBr o RX
+ HBr Idem 1° zonder HBr
+ PBr3 o ROSO3H
+ PBr5 + Koud,
o RCl geconcentreerd
+ SOCl2 (zonder base H2SO4 (SN1)
intramoleculair = 3°ROH (SN1)
behoud configuratie) o Enkel HBr, HCl en HI
+ PCl3
+ PCl5 Eliminatie
+ POCl3 Deshydratatie
+ ZnCl2 o + Warm, geconcentreerd
o RSO2R’ (sulfonaatesters, geen H2SO4
inversie) 1° ROH E2
+ ClSO2R’ 2° of 3° ROH E1
o 1. Halogeneren en 2. E2
Oxidaties (Niet bij 3°ROH)
+ Cr (VI+)
o Keton/carbonzuur
+ PCC/CH2Cl2 of OCl-
Tosylchloride o Keton/aldehyde
, Ethers
+ HX RX + ROH (SN1/2 via protonering)
Epoxiden
Ringopening onder zure omstandigheden of door nucleofiele aanval (altijd trans)
Aminen
4° N+ OH- Hofmann eliminatie
Amine + H202 RNHOH
Thiolen
Analoog aan ROH, maar kunnen ook RS-Hg-SR
Organometaalverbindingen
Li vervangt X, Mg bindt aan Br (Grignard reagens), reageren als C- (ZB gaat sneller op)
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