Important functional group interconversions in aromatic systems Flashcards
from NH2 –> F
i) HNO2 ii) BF4- / /\ (heat)
from NH2 –> Cl
i) HNO2 ii) Cu2Cl2
Sandmeyer reaction
from NH2 –> Br
i) HNO2 ii) Cu2Br2
Sandmeyer reaction
from NH2 –> I
i) HNO2 ii) KI
from CN –> Br
i) HNO2 ii) Cu2(CN)2
from NH2 –> SR
i) HNO2 ii) NaSR
from NH2 –> OH
i) HNO2 ii) H2O / /\ (heat)
from NH2 –> N3
i) HNO2 ii) NaN3
from NH2 –> NO2
- i) HNO2 ii) NaNO2
- CF3CO3H
oxidation
from NH2 –> H
i) HNO2 ii) H3PO2
technically FGA/FGR
from SO3H –> H
steam; or H20 / /\ (heat)
technically FGA/FGR
from NO2 –> NH2
- Sn/ HCl; or H2/ Pd
reduces 2 or more groups - Na2S
reduces 1 of 2 groups
from COCl –> CONR1R2
R1R2NH
technically C-N
from COCl –> CO2R
ROH
technically C-O
from CO2H –> CO2R
ROH / H+ / /\ (heat)
technically C-O
from CO2H –> COCl
SOCl2
from CH3 –> CO2H
KMnO4 (alkaline)
OK for larger alkyl groups
from CH=O –> CO2H
CrO3; or K2Cr2O7
oxidation
from CH2OH –> CH=O
MnO2
controlled oxidation
from CH=O –> CH2OH
NaBH4; LiAlH4
reduction
from COR (ketone) –> CHROH
NaBH4; or LiAlH4
reduction
from NH2 –> NHCOR
RCOCl or (RCO)2O
technically C-N
from NHCOR –> NH2
OH- / H2O / /\ (heat)
hydrolysis
from OH –> OCOR
RCOCl or (RCO)2O
technically C-O
from OCOR –> OH
OH- / H2O / /\ (heat)
hydrolysis
from COR (ketone) –> CH2R
i) HSCH2CH2SH ii) H2 Raney Ni
FGA/FGR
i) Zn / Hg / HCl
acidic FGA/FGR
i) H2NNH2 / KOH / /\ (heat)
basic FGA/FGR
