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Samenvatting reacties Organische Chemie
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H1-11Reactie Eigenschappen Regels Carbokation Katalyse Beginproducten Eindproducten
Elektro ele Stereospeci ek Markovnikov Ja Alkeen + HX → halogeenalkaan
additie Alkyn + HX → halogeenalkeen + HX →
dihalogeenalkaan
Additie water Markovnikov Ja H2SO4 Alkeen + H2O (H2SO4) → alcohol
Alkyn + H2O (H2SO4) → enol → keton
Additie alcohol Markovnikov Ja H2SO4 Alkeen + -OH (H2SO4) → ether
Additie Markovnikov Nee Alkeen + X2 → vincinaal dihalogeen
halogeen
Hydroboratie Anti- Nee 1.THF Alkeen + BH3 (1.THF 2. H2O2/H2O) → alcohol
Markovnikov 2. H2O2/H2O Alkyn + BH3 → (THF) → B-gesubstitueerd alkeen
→ (1.THF 2.2. H2O2/H2O) → enol → keton
HgSO4 Terminaal alkyn + BH3→(H2O2/H2O, HgSO4) → alcohol→ keton
Disamyl-B →(disa-B,H2O2/H2O) → alcohol→ aldehyde
Hydrogenatie Reductie Nee Pt/C, Pd/C, Ni Alkeen + H2 → (Pt/C, Pd/C, Ni) → alkaan
Lindlar Alkyn + H2 → (Pt/C, Pd/C, Ni) → alkeen → alkaan
→ (Lindlar) → cis-alkeen
Sn1 2 stappen (1e Ja NaEtO LG vervangen met Nu:
orde) KOtBu Sec/tert alcohol + HBr → halogeenalkaan + H2O
Tert > sec (≠ prim) = Neutraal Nu: ~ Epoxide + HX → (ROH) → R’-CROH-COH
Nu: = ZWB Benzeen + E+ → (B) → benzeen-E+
LG = ZWB
Protisch solvent
1
fi fi
, Sn2 1stap (2e orde) Nee DMSO LG vervangen met Nu:
Prim > sec (≠ tert) DMF Prim alcohol + HBr → halogeenalkaan +H2O
Nu: = STB, ↑C Aceton Prim/sec alcohol + PBr3 → (pyridine) → halogeenalkaan
LG = ZWB Geladen of Prim/sec alcohol + SOCl2 → (pyridine) → halogeenalkaan +SO2
A/protisch solvent neutraal Nu: Alcohol + TsCl → (pyridine) → ROT → (B) → ROCH + OTs-
Ether + HI/Br (∆) → halogeenalkaan + alcohol
~ Epoxide + X- → R’-COH-CROH
Bescherming: alcohol + (CH3)3SiCl ⇄ (TMS)ether
BuLi Alkylhalide + (C6H5)3P| → R-PPh3
Alkylering ≠ Alkylering: carbonyl + LDa/THF → canbonylanion + RX→
aldehyde mono-gealk keton
E1 2 stappen (1e 6-ring: H en Ja T Vorming dubbele C=C-binding
orde) LG anti NaEtO Dehydratie: sec/tert alcohol + H2SO4 (∆) → alkeen + H2O
Tert > sec (≠ prim) Zaitsev KOtBu
Nu: = ZWB = Neutraal Nu:
LG = ZWB
Protisch solvent
E2 1stap (2e orde) Zaitsev Nee T Vorming dubbele C=C-binding
Prim > sec > tert DMSO Dehydratie: prim alcohol + H2SO4 (∆) → alkeen + H2O
Nu: = STB, ↑C DMF
LG = ZWB Aceton
A/protisch solvent Geladen of
neutraal Nu:
Grignard Ketenverlenging
Chlorering Nee hv of ∆ Alkaan + Cl2 → (hv/∆) → chlooralkaan + HCl
Bromering Nee hv of ∆ Alkaan + Br2 → (hv/∆) → broomalkaan + HBr
Alkeen + NBS → (hv/∆, peroxide) → broomalkeen + HBr
Halogenering Ja FeBr3/Cl3 Benzeen + Br+/Cl+ → (FeBr3/Cl3) → benzeen-Br/Cl + HBr/Cl
Nitrering Ja H2O, H2SO4 Benzeen + HNO3 → (H2O, H2SO4) → benzeen-NO2 + H2O
Sulfonering Reversibel met Ja ∆, H2SO4 Benzeen + H2SO4 → (∆, H2SO4) → benzeen-SO3H + H2O
H3O+ en 100℃
Friedel-Craft Ja 1. AlCl3 2.H2O Benzeen + RCOCl → (1. AlCl3, 2.H2O) → benzeen-COR+ HCl
Acylering
2
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