conc. HNO3, conc. H2SO4 catalyst, 50-60 C
nitration / electrophilic substitution
Sn / conc. HCl
reduction
Br2
Electrophilic Substitution
Br2 / AlBr3 or Fe or FeBr3
Bromination / Electrophilic Substitution
CH3Cl, AlCl3 catalyst, anhydrous
alkylation / electrophilic substitution
Cl2 / AlCl3 or Fe or FeCl3
chlorination / electrophilic substitution
CH3COCl, AlCl3 catalyst, anhydrous
acylation / electrophilic substitution
NaBH4
reduction
dilute HNO3
nitration / electrophilic substitution
Br2
bromination / electrophilic substitution
NaOH(aq)
H2 / Ni, 150 C
Electrophilic Addition / hydrogenation
Alkene → Alkane
Hydrogen halide, room temp
electrophilic addition
Alkene → Haloalkane
H2O (steam) / H3PO4
hydration
Alkene → Alcohol
Halogen, UV
free radical substitution
Alkane → Haloalkane
NaCN or KCN in ethanol
nucleophilic substitution
Haloalkane → Nitrile
NH3 in ethanol
nucleophilic substitution
Haloalkane → Amine
NaOH(aq), reflux
nucleophilic substitution
Haloalkane → Alcohol
K2Cr2O7 / H2SO4, distill
oxidation
Alcohol → Aldehyde
K2Cr2O7 / H2SO4, reflux
oxidation
Alcohol → Carboxylic Acid
Al2O3 or conc. H2SO4 or conc. H3PO4 / heat
elimination / dehydration
Alcohol → Alkene
Sodium Halide / H2SO4, heat under reflux
nucleophilic substitution
Alcohol → Haloalkane
Carboxylic acid/ conc. H2SO4 or Acid anhydride or Acyl chloride
Esterification
Alcohol → Ester
NaCN(aq) / H+(aq)
nucleophilic addition
Adlehyde / Ketone → Hydroxynitrile
NaBH4 / H2O
Reduction
Aldehyde / Ketone → Alcohol
hot aqueous alkali
alkaline hydrolysis
Ester → Carboxylate salt
Alcohol / conc. H2SO4
esterification
Carboxylic acid → Ester
SOCl2
chlorination
Carboxylic acid → Acyl chloride
H2O
hydrolysis
Acyl chloride → Carboxylic acid
NH3
nucleophilic addition elimination
Acyl chloride → Primary amide
Primary amine
nucleophilic addition elimination
Acyl chloride → Secondary amide
Alcohol
Acyl chloride → Ester
H2 / Ni
Nitrile → Amine
dilute hot aqueous acid
acid hydrolysis
Ester → Carboxylic acid
H2O, HCl, heat
hydrolysis
Nitrile → Carboxylic acid
K2Cr2O7 / H2SO4, reflux
oxidation
Aldehyde → Carboxylic Acid
K2Cr2O7 / H2SO4, reflux
oxidation
Alcohol → Ketone
H2 / Ni
Hydroxynitrile → Amine