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Summary Organic Chemistry Spiekbrief 2 BFW
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Cheat sheet for the course Organic Chemistry 2 BFW. You can take this cheat sheet with you to the exam and all the exam material is on it.
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Reactie Uitgangsstof Reagentia Product Let OpNuc Sub Z/B
Bronsted Zuur, bijv: H-A Base, bijv: H2O A- + H3O+ Zuur,≠nucbase,Base pKa zuur
Alkyl (O/P
NH2 (O/P)
OH (O/P)
EDG
Hard
Intermediair
Zacht
Lewis Zuur=Elektrofiel bv: BF3 Base:Nucleofiel bv: NH3 H3N+-B-F3 VEP = vaak nucleofiel H2SO4 -9
Sn1 R3CX Nuc R3C-Nuc Ster. Hind. HI -9
Sn2 RCH2X Nuc RCH2-Nuc Kan Sn1 als R lading stabliseert HCl -7
N.A.S/1,4ad/el EWG-Aro-X Nuc EWG-Aro-Nuc X kan F F3CCOOH -0.3
1,2 add/elim R(C=O)X Nuc,bv Grignard R(C=O)Nuc Pka HX laag H2SO3 1.9
Halogen (O/P)
Carbonyl(M).C=O
NO2 (M)
EWG
RO-,OH-,F-
Br-,N3-,C-N
RSH,RS-
Nucleofiel
H3PO4 2.1
Nuc Add
Weinreb R(C=O)N(CH3)OCH3 Grignard R(C=O)CH3 MgBr comple|LiALH4->ket
HF 3.2
Verzeping R(C=O)OR’ NaOH R(C=O)OH Opw.
CO3H2 3.6 & 10.5
Verestering R(C=O)Cl Pyridine|HOR’ R(C=O)OR’ Niet nuc base->Sn2
CH3COOH 4.8
Verestering R(C=O)OH HCl(dry)|HOR’ R(C=O)OR’ Fischer chemie Pyridine 5.25
Michael Ring=O met = Bv. NaNH2|opw. Ring(=O)-NH2 1,4 additie
Li+,H+,Mg,(CH3)3SiCl
Zn
RCH2Br,RCH2I,I2,Cu,Hg
Electrofiel
PhSH 7.8
Eliminatie
E1 R2COH-CH3 H2SO4 R2C=CH2 z/b->carb. kat HCN 9.1
E2 HC-CX Niet-nuc base C=C Gelijktijdig PhOH 10
E1cb EwgC-CH2-CH2X Sterke base (NaH) EwgC-C=C 2 stappen≠E2 CH3NO2 10.2
Red. Aminering R-NH2 H(C=O)H|Buf.Ph6|NaB R-N(H)-CH3 Ald reactiever > imminium K2+CO32- 10.3
H3CN !NaBH3CN! DiPEA 10.8
Reductie
Hydrogeneren HR(C=C)HR H2|Pd-C H2R(C-C)H2R Kan op R-≡-R|≠selectief Et3N 11
Luche R(C=O)R CeCl3|NaBH4 R(C-OH)HR Selectief (1,2) DBU 12
Rosenmund R(C=O)Cl H2|Pd,BaSO4 R(C=O)H Quinoline voor HCL CH3OH 15.5
H2O 15.7
Lindlar R-(C≡C)-R H2|Pd,CaCO3|Pb(OAc)2 HR(C=C)HR Selectief (cis)
CH3CH2OH 17
Nitro reductie R-NO2 Pd-C + H2 R-NH2 Kan ook met: Fe/Sn/Zn + HCl
xyleren Oxidatie Hydrolyse
KOtBu 19
Cyano->carbzuur R-C≡N H2O + HCl R-(C=O)OH OH- maakt carboxylaat tert-butanol 19
Amide R(C=O)-(NH)R H2O R(C=O)OH + H2N-R Vormt carbzuur en amine Aceton (C3H6O) 19
Ester Ester H2O Carbonzuur + Alcohol CHCl3 25
Jones (prim alc) R(C-OH)HH Na2Cr2O7|H2SO4 R(C=O)OH (carbonzuur) Via het aldehyde|niet selectief HCCH 26
Jones (sec alc) R(C-OH)R’H Na2Cr2O7|H2SO4 R(C=O)R’. (keton) H2/NaH 35
Swern R(C-OH)HH Oxalylchl|2Et3N|DMSO R(C=O)H Selectief=prim LDA 36
alc>ald|Jones=prim alc>carb z Na+NH2- 36
Decarbo
Decarbox. R(C=O)CH2-C(=O)O verhitten CO2+R(C=O)CH3 Beta-ketozuur NH3 37
Krapcho R(C=O)CH2-C(=O)CH3 NaCl|DMSO|verhitten CO2+H3CCl(g)+ R(C=O)CH3 Beta-keto-methylester|hoge T H2CCH2 44
Grignard R(C=O)R CH3MgBr R(C-O)(CH3)R Hard=1,2 add CH3(CH2)3Li 50
H3CCH3 >51
Grignard +Cu Aro + = + ewg CH3MgBr|CuCl CH3 op 4-plek Zacht=1,4 add
Alkyleren
Gillman Aro + = + ewg (CH3)2CuLi CH3 op 4-plek Zacht=1,4 add
Meerwein zout H3C(C=O)R NaH|Me3OBF4 CH2(C=C)OMeR Hard=O alkyleren
Alk. met NaH H3C(C=O)R NaH|CH3Br CH3CH2(C=O)R Zacht| Opw.
O-acylering CH3(C=O)CH3 NaH|Cl(C=O)CH2 C(C=O)O(C=C)C F.C. acyl. kan ook
eren
Acyl
Friedel-Crafts Aromaat CH3(C=O)Cl + AlCl3 Aromaat-(C=O)CH3 Geen overacylering.
Haloform R(C=O)CH3 4NaOH|3X2 R(C=O)ONa,CX3H X:Br/I.bij:3NaX,H2O
Aldol 2H3C(C=O)H Base bijv NaOH Me(C-OH)CH2(C=O)H Aldehyde+Alcohol.
Nitro-aldol R(C-NO2)R + H(C=O)R Base bijv NaOH RR(C-NO2)-(C-OH)HR
Enolaat chemie
Claisen 2H3C(C=O)OEt NaOEt H3C(C=O)CH2(C=O)OEt Zelfde base ester. -HOEt -NaOEt
Dieckmann Diester NaOEt Ring (beta-keto ester) =intramoleculaire Claisen
Knoevenagel Diester R(C=O)H,piperidine Diester=CHCH3 Zwakke base
HWE Fosfonaat R(C=O)H, NaOEt RH(C=C)(C=O)OEt Trans (Ster. Hind.)
Wittig Onstabiel R(C=O)H bv. Ph3P=CH2 . =onst. RH(C=C)H2 (cis) Onstabiel reagens = cis
Wittig Stabiel R(C=O)H Bv. Ph3P=C-EWG RH(C=C)EWGH (trans) Stab.reagens:Trans zie tabel EWG
Mannich R(C-OH)=CH2 H2C=N+(CH3)2)I- R(C=O)CCN+(CH3)2 Enol|Eschenmoser
E.A.S. Aromaat E+X - Aromaat-E + HX EDG->ortho/para
Nitrering Aromaat HNO3|H2SO4 Aromaat-NO2 Via O=N=O (z/b)
Elec sub
Kolbe Schmitt Fenol (aro) NaOH|CO2 Fenol-CO2 Aro=gunstig
Friedel-Crafts Aromaat H3CCl|AlCl3 Ar-CH3|AlCl3.HCl Overalkylering
MonoBr (EAS) Aromaat Br2|AlCl3 Ar-Br|HBr.AlCl3 Zie Friedel Crafts
nium ering Elec add
MonoBr(Enol) R(C=O)CH3 Br2|azijnzuur R(C=O)CH2Br Azzuur anders halo
Hydrobromering Me2(C=CH2) HBr Me3(C-Br) Carbokat hyperconj
Dibromering ≠ ar wel ring met = Br2 Ring-Br-Br Via bromonium
Epoxidering Ring=O met = NaO-OH Epox aan ring=O Via Michael
Diazo Epoxid
Epoxidering Aromaat MCBPA Epox aan ring Electrofiele add.
Diazotering R-NH2 NaNO2|2HCl R-N2+Cl- Bijprod: NaCl,H2O
Sandmeyer R-N2+Cl- CuXofH2O+H2SO4 R-X of R-OH X=halogeen of CN
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