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Alkane to Haloalkane
Oxidation: Cl2, UV light
Haloalkane to Amine
Substitution: NH3 (ammonia)
Haloalkane to alkene
Elimination: (conc) KOH in ethanol
alkene to haloalkane
Electrophilic Addition: HCl
Alkene to alkane
Reduction: H2, Nickel Catalyst
Alkene to Alcohol
Hydrolysis (/dehydration): use catalytic conc H2SO4 and water
Alcohol to Chloroalkane
Substitution. NaOH and PCl5
Alcohol to bromoalkane
Substitution: 50% conc H2SO4 and KBr
Alcohol to Iodoalkane
Substitution: Red phosphorus and Iodine:
2P + 3I2 —> 2PI3
Alkene to diol
Oxidation: KMnO4
Alcohol to Aldehyde/ketone/carboxylic acid
Oxidation: K2Cr2O7 and conc H2SO4
carboxylic acid or aldehyde to alcohol
Reduction: LiAlH4, dry ether
Haloalkane to Nitrile
(Oxidation (or substitution)) CN- ions eg. KCN (SN1/SN2)
Nitrile to amine
Reduction: LiAlH4, dry ether
Carboxylic acid to ester
Alcohol, H2SO4, heat
ester to carboxylic acid
(saponification!) NaOH and H2O
Carboxylic Acid to Acyl Chloride
PCl5
acyl chloride to amide
Substitution: NH3
Nitrile to carboxylic acid
Heat with HCl
Note
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