6.2.5 Synthetic routes (not aromatic) Flashcards
alkene -> polyalkene
high pressure
catalyst
polymerisation
alkene -> dihaloalkane
Br2, Cl2
room temp
electrophilic addition
alkene -> alkane
H2
nickel catalyst
addition/reduction
alkane -> haloalkane
Br2,Cl2
UV light
free radical substitution
alkene -> haloalkane
HBr, HCl
room temp
electrophilic addition
alkene -> alcohol
H2O (g)
using conc phosphoric acid catalyst (H3PO4)
alcohol -> alkene
conc H2SO4 or conc H3PO4
elimination, dehydration
alcohol -> haloalkane
NaBr and H2SO4
heat under reflux
substitution
haloalkane -> alcohol
KOH aqueous
heat under reflux
nucleophilic substitution
haloalkane -> amine
alcoholic NH3
heat under pressure
nucleophilic substitution
haloalkane -> nitrile
CN- and ethanol
nucleophilic substitution
nitrile -> amine
H2
nickel catalyst
reduction
amine -> secondary/tertiary amine
haloalkane
nucleophilic substitution
amine -> secondary amide
acyl chloride
room temperature
nucleophilic addition/elimination
nitrile-> carboxylic acid
acid hydrolysis
heat with HCl
alcohol -> aldehyde
Na2Cr2O7/H+
primary alcohol
heat gently and distill
partial oxidation
alcohol -> ketone
Na2Cr2O7/H+
secondary alcohol
heat under reflux
oxidation
aldehyde -> alcohol
NaBH4
reduction
ketone -> alcohol
NaBH4
reduction
ketone -> hydroxynitrile
HCN and KCN
Nucleophilic addition
Aldehyde -> hydroxynitrile
HCN and KCN
nucleophilic addition
Aldehyde -> carboxylic acid
Na2Cr2O7/H+
Heat under reflux + excess oxidising agent
Oxidation
Carboxylic acid -> acyl chloride
SOCl2
Acyl chloride -> carboxylic acid
H2O room temp
Carboxylic acid -> ester
Alcohol and H2SO4
Heat
Esterification
Acyl chloride -> ester
Alcohol
Room temp
Alcohol -> ester
Carboxylic acid + H2SO4
Heat
Esterification
Acyl chloride -> secondary amide
Primary amine
Room temperature
Acyl chloride -> primary amide
NH3 room temperature
How can esters and amides be hydrolysed
By NaOH and acids