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Samenvatting Organische chemie 2 reactiemechanismen $4.87   Add to cart

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Samenvatting Organische chemie 2 reactiemechanismen

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Schema reactiemechanismen

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  • December 30, 2022
  • 42
  • 2020/2021
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Reacties
Alkanen
 +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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