Aliphatic Synthetic Routes Flashcards
Alkane to haloalkane
Free Radical substitution
Cl2/Br2/I2 + ultraviolet light
Alkene to Alkane
Hydrogenation
H2(g) + Ni catalyst
Alkene to Haloalkane
Electrophilic addition
HCl/ HBr / HI
Alkene to Alcohol
Hydration
H2O(g) + heat + H3PO4 catalyst
Alcohol to Alkene
Dehydration
H3PO4 catalyst + heat
Haloalkane to Alcohol
Nucleophilic Substitution
NaOH(aq)
Alcohol to Haloalkane
Nucleophilic substitution
NaCl / NaBr / NaI +H2SO4 catalyst
Haloalkane to Nitrile
Nucleophilic Substitution
KCN/ ethanol
Haloalkane to Primary Amine
Nucleophilic Substitution
NH3/ethanol (excess NH3)
Haloalkane to Secondary/ Tertiary Amine
Nucleophilic Substitution
NH3/ ethanol (excess Haloalkane)
Nitrile to Primary Amine
Reduction
H2(g) + Ni catalyst
Nitrile to Carboxylic acid
Acid hydrolysis
Dilute HCl
Primary Alcohol to Carboxylic acid
Oxidation
Acidified Potassium dichromate
Reflux
Primary Alcohol to aldehyde
Oxidation
Acidified Potassium dichromate
distillation
Secondary Alcohol to Ketone
Oxidation
Acidified Potassium dichromate
Reflux
Aldehyde to Carboxylic acid
Oxidation
Acidified Potassium dichromate
Reflux
Aldehyde to Primary Alcohol
Reduction
NaBH4(aq)
Ketone to Secondary Alcohol
Reduction
NaBH4(aq)
Aldehyde/Ketone to Hydroxynitrile
Nucleophilic addition
NaCN(aq) + H+(aq)
Primary Amine to Amide
Condensation
Acyl Chloride
Carboxylic acid to Acyl Chloride
SOCl2
Acyl Chloride to Carboxylic acid
Hydrolysis
H2O
Acyl Chloride to Amide
Condensation
NH3 or Amine
Carboxylic acid to Ester
Esterification
Alcohol + Conc H2SO4 catalyst
Acyl Chloride to Ester
Esterification
Alcohol
Acid Anhydride to Ester
Esterification
Alcohol
Esther to Alcohol + Carboxylate salt
Base hydrolysis
NaOH
Esther to Alcohol + Carboxylic acid
Acid Hydrolysis
(moderately concentrated ) HCl + H2O