4 Synthetic Routes Flashcards
Haloalkane to alcohol
NaOH (aq) (or water or ammonia???)
Reflux
(Halogen is replaced by -OH. Makes Sodium halide)
Alkane to haloalkane
Halogen/UV Haloalkane and hydrogen halide E.g. bromomethane and HBr Radical substitution Initial stage Propagation Termination
Alkene to haloalkane
Hydrogen halide or halogen
Electrophilic addition
Curly arrow from double bond to electropositive atom. Single bond to electroneg atom.
Alkene to alkane
H2
Ni catalyst
423Kelvin (150oC)
Alkene to alcohol
H2O(g) (steam)
H3PO4 catalyst
Hydration
Alcohol to haloalkane
Sodium halide
H2SO4
Substitution reaction
Sodium halide + sulfuric acid -> NaHSO4 + Hydrogen halide
The hydrogen halide produced is used in reaction
Alcohol + hydrogen halide -> haloalkane + H2O
Produces water
Alcohol to alkene
Dehydration
Water molecule removed
Heated under reflux in presence of phosphoric acid catalyst
Primary alcohol to carboxylic acid
K2Cr2O7/H2SO4 Heated under Reflux Oxidation Alcohol + 2[O] -> carboxylic acid + H2O Produces water The dichromate ions change colour from orange to green
Primary Alcohol to aldehyde
K2Cr2O7/H2SO4 Distilled Oxidation Alcohol + [O] -> aldehyde + water Produces water
Secondary alcohol to ketone
K2Cr2O7/H2SO4 Heated under reflux Oxidation Alcohol + [O] -> Ketone + water Produces water The dichromate ions change colour from orange to green
haloalkane to nitrile
NaCN
ethanol
haloalkane to amine
NH3
ethanol
primary alcohol to ester
carboxylic acid
conc H2SO4
nitrile to amine
H2
Ni catalyst
nitrile to carboxylic acid
H2O
HCl
heat
forms carboxylic acid and NH4Cl
carboxylic acid to ester
alcohol
conc H2SO4
carboxylic acid to acyl chloride
SOCl2
produces acyl chloride + SO2(g) + HCl(g)
aldehyde to primary alcohol
NaBH4/H2O
aldehyde to carboxylic acid
K2CR2O7/H2SO4
reflux
aldehyde to hydroxynitrile
HCN
H2SO4/NaCN
ester to carboxylic acid and alcohol
dil acid hydrolysis
H+/H2O
heat
ester to sodium salt of COOH and alcohol (carboxylate)
NaOH/H2O
alkaline hydrolysis
heat
acyl chloride to ester
alcohol
acyl chloride to carboxylic acid
H2O
acyl chloride to primary amide
NH3
acyl chloride to secondary amide
primary amine
benzene to nitrobenzene
HNO3
H2SO4
50oC
nitrobenzene to phenylamine
Sn/conc HCl
NaOH?????
phenylamine to tribromophenylamine
Br2
benzene to bromobenzene
Br2
FeBR3
benzene to chlorobenzene
Cl2
AlCl3
benzene to methylbenzene
CH3Cl
AlCl3
benzene to benzene ketone ??
C6H5COCH3
CH3COCl
AlCl3
phenol to nitrophenol
dil HNO3
phenol to sodiumphenoxide
NaOH(aq)
phenol to tribromophenol
Br2
nitrobenzene to bromonitrobenzene
Br2
FeBr3
high temp
ROH + NaCl + H2SO4 –>
RCl + NaHSO4 + H2O
water in and out of condenser
water in at bottom
RCN + acid
RCOOH
MP of impure compound
lower than MP of pure compound
reason for heating under reflux
to prevent any substances escaping
haloalkane + H2O (+AgNO3 + ethanol)
alcohol + AgX
radical substitution limitations
further substitution
substitution at diff positions on chain
homologous series
same functional groups, diff carbon chain length
each successive member differs by CH2
anhydrides and alcohol
ester
anhydrides dont react w carboxylic acids
kekule and delocalised model similarities
overlap of p orbitals
pi ring above and below
kekule and delocalised model differences
K has alternating pi bonds
delocalised has pi ring
