Synthetic Routes Flashcards
Alkane to haloalkane
X2, UV light, free radical substitution
Haloalkane to Amine
Excess ethnanolic ammonia (or amines)
Heat
Haloalkane to Nitrile
NaCN or KCN,
Ethanol,
Reflux
Nucleophilic substitution
Nitrile to Amine
LiAlH4, Then dilute acid. (Lab) - reduction
Or Na and ethanol, reflux.
Or H2, Ni/pt catalyst, high temp and pressure (Industry) - catalytic hydrogenation
Nitrile to carboxylic acid
Dilute HCl, reflux (hydrolysis)
Hydroxynitrile to amine
LiAlH4, Then dilute acid. (Lab) - reduction
Or Na and ethanol, reflux.
Or H2, Ni/pt catalyst, high temp and pressure (Industry) - catalytic hydrogenation
Hydroxynitrile to carboxylic acid
Dilute HCl, reflux (Hydrolysis)
Alkene to alkane
H2, nickel catalyst, 150℃
Alkene to dihaloalkane
X2, 20℃
Alkene to alcohol
Steam, H3PO4 catalyst, 300℃, 60-70atm
Alcohol to alkene
Conc. H2SO4 or H3PO4, 170℃
Haloalkane to alcohol
Warm NaOH OR KOH, H2O, reflux
Alcohol to haloalkane
NaX, H2SO4, 20℃
Alcohol to Ester
Carboxylic acid, acid catalyst, heat. - esterification
OR acyl chloride.
Or acid anhydride
Ester to alcohol
Dilute acid or alkali,
Reflux
-hydrolosis
Alcohol to aldehyde/ketone
Acidified potassium dichromate, heat
Aldehyde/ketone to Alcohol
NaBH4 then water - aldehyde gives primary, ketone give secondary
Aldehyde/Ketone to hydroxynitrile
HCN
-Nucleophilic addition
Aldehyde to carboxylic acid
Acidified potassium dichromate, reflux
Oxidation
Hydroxynitrile to carboxylic acid
Dilute HCl,
Reflux
Carboxylic acid to ester
Alcohol,
Acid catalyst
Heat
Ester to carboxylic acid
Dilute acid or alkali,
Reflux
Carboxylic acid to acyl chloride
SOCl2
Acylc chloride to carboxylic acid
Cold H2O
Acyl chloride to amide
NH3, 20℃ (to make primary amide)
Amine, 20℃ (to make secondary amide)
Acyl chloride to ester
Alcohol, 20℃
Benzene to nitrobenzene
conc. HN03
conc.H2SO4
warm
Nitrobenzene to phenylamine
Tin, conc. HCl reflux then NaOH
Benzene to Halobenzene
X2,
AlCl3 catalyst,
warm
Benzene to Alkyl Benzene
Haloalkane AlCl3 catalyst
reflux
Benzene to phenylketone
Acyl chloride
AlCl3 catalyst
reflux
Phenol to 2,4,6-tribromophenol
Bromine water (Br2) 20℃
Phenol to sodium phenoxide
NaOH
20℃
Phenol to phenyl esters
acyl chloride
20℃
Phenol to 2-nitrophenol, or 4 nitrophenol
Dilute HN03,
20℃