Synthetic Routes Flashcards
Alkane to haloalkane
X2 (halogen)
UV light
Haloalkane to alcohol
Warm NaOH or KOH, H2O
Reflux
Alcohol to haloalkane
NaX, H2SO4
20°C
Alcohol to aldehyde
K2CrO7, H2SO4
Heat primary alcohol in distillation apparatus
Aldehyde to carboxylic acid
K2CrO7, H2SO4
Reflux
Alkene to dihaloalkane
X2 (halogen molecule)
20°C
Alkene to alcohol
Steam, H3PO4 catalyst
300°C, 60-70 atm
Alcohol to alkene
Conc H2SO4 or H3PO4
Heat
Alkene to haloalkane
HX
20°C
Alkene to alkane
H2, nickel catalyst
150°C
Alcohol to ketone
K2Cr2O7, H2SO4
Heat secondary alcohol in reflux apparatus
Haloalkane to nitrile
NaCN or KCN
Ethanol
Reflux
Haloalkane to amine
Excess ethanolic NH3 (or amines)
Heat
Nitrile to amine
LiAlH4 then dilute acid
Or Na and ethanol, reflux
Or H2, Ni/Pt catalyst, high temperature and pressure
Nitrile to Carboxylic acid
Dilute HCl
Reflux
Hydroxynitrile to carboxylic acid
Dilute HCl
Reflux
Ketone to 2° alcohol
NaBH4 then water
Aldehyde to hydroxynitrile
HCN or NaCN
Ketone to hydroxynitrile
NaCN or HCN
Hydroxynitrile to amine
LiAlH4 then dilute acid
Or Na and ethanol, reflux
Or H2, Ni/Pt catalyst, high temp and pressure
Aldehyde to 1° alcohol
NaBH4 then water
Alcohol to carboxylic acid
K2Cr2O7
H2SO4
Reflux
Alcohol to ester
Carboxylic acid, H2SO4 catalyst, heat
Or acyl chloride
Or acid anhydride
Carboxylic acid to ester
Alcohol, H+ (acid) catalyst
Heat
Ester to carboxylic acid
Dilute acid or alkali
Reflux
Ester to carboxylate
OH-
Heat
Acyl chloride to ester
Alcohol
20°C
Carboxylic acid to acyl chloride
SOCl2
Acyl chloride to carboxylic acid
Cold H2O
Acyl chloride to 1° amide
NH3
20°
Acyl chloride to 2° amide
Primary amine
20°
Benzene to nitrobenzene
Conc HNO3
Conc H2SO4
Warm
Benzene to halobenzene
X2
AlCl3 catalyst
Warm
Benzene to alkyl benzene
Haloalkane
AlCl3 catalyst
Reflux
Benzene to phenylketone
Acyl chloride
AlCl3 catalyst
Reflux
Nitrobenzene to phenylamine
Tin
Conc HCl
Reflux then add NaOH
Phenol to sodium phenoxide
NaOH
20°
Phenol to phenyl ester
Acyl chloride
20°
Phenol to 2-nitrophenol or 4 nitrophenol
Dilute HNO3
20°
Phenol to 2,4,6 tribromophenol
Bromine water (Br2)
20°
Methyl benzene to benzoic acid
Alkaline MnO4
H2SO4