Aliphatic synthetic routes Flashcards
Alkane —> Haloalkane
Halogen/UV light
FREE RADICAL SUBSTITUTION
Alkene—> Alkane
H2/ Ni catalyst
423K
Alkene —> Haloalkane
X2 or HX
(Halogen or hydrogen halide)
ELECTROPHILIC ADDITION
Alkene —> Alcohol
Steam (H2O)/ H3PO4 catalyst
Haloalkane —> Alcohol
NaOH (aq)/ Reflux
NUCLEOPHILIC SUBSTITUTION
Haloalkane — > Nitrile
NaCN or KCN in ethanol
NUCLEOPHILIC SUBSTITUTION
Haloalkane —> Amine
Excess NH3, in Ethanol
NaOH added to generate amine from the salt
NUCLEOPHILIC SUBSTITUTION
Alcohol —> Haloalkane
NaX/ H2SO4
HX formed in situ
Heat w/ reflux
Alcohol —> Alkene
Heat under reflux/ conc H2SO4 or conc H3PO4
Secondary Alcohol —> Ketone
K2Cr2O7/ H2SO4
Reflux
OXIDATION
Primary Alcohol —> Aldehyde
K2Cr2O7/ H2SO4
Distillation
OXIDATION
Aldehyde —> Primary alcohol
NaBH4
REDUCTION
Ketone —> Secondary alcohol
NaBH4
REDUCTION
p
Primary alcohol —> Carboxylic acid
K2Cr2O7/ H2SO4
Reflux
OXIDATION
Alcohol —> Ester
- Carboxlyic acid/ conc H2SO4 catalyst
- Acid Anhydride
- Acyl Chloride
Carboxylic acid —> Ester
Alcohol/ conc H2SO4 catalyst
Ester —> Carboxylic acid
Dilute Acid, Reflux
ACID HYDROLYSIS
Ester —> Carboxylate
OH- (aq)
Reflux
ALKALI HYDROLYSIS
Acyl chloride —> Ester
Alcohol
Carboxylic acid —> Acyl chloride
SOCl2
Acyl chloride —> Carboxylic acid
H2O
Ketone —> Hydroxynitrile
NaCN/ H+ (aq)
HCN formed in situ
NUCLEOPHILIC ADDITION
Aldehyde —> Hydroxynitrile
NaCN/H+ (aq)
HCN formed in situ
NUCLEOPHILIC ADDITION
Hydroxynitrile —> Amine
H2/ Ni catalyst
Nitrile —> Amine
H2/ Ni catalyst
Nitrile —> Carboxylic acid
H2O/ HCl
Heat
HYDROLYSIS
Acyl chloride —> Primary amide
NH3
Acyl chloride —> Secondary amide
Primary amine
