Functional Group Conversions
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Alkene to alkane
H2 with Ni or Pt catalyst
Alkane to haloalkane
Cl2 or Br2 with UV light
Alkene to monohaloalkane
HBr or HCl Addition Check for the possible major/minor products from Markovnikov’s rule
Alkene to dihaloalkane
Cl2 or Br2 Addition
Alkene to alcohol
H2O/H+ aka dilute acid Addition Check for possible major/minor products from Markovnikov’s rule
Alkene to diol
MnO4-/H+ Addition/Oxidation
Haloalkane to alkene
KOH(alc) Elimination Check for possible major/minor products from Zaitsev’s rule
Haloalkane to alcohol
KOH(aq) Substitution
Haloalkane to amine
c.NH3 or NH3(alc) or R-NH2 Substitution
Alcohol to alkene
c.H2SO4 Elimination
Alcohol to ketone
MUST be secondary alcohol MnO4-/H+ or Cr2O72-/H+ Reflux Oxidation
Alcohol to aldehyde
MUST be primary alcohol MnO4-/H+ or Cr2O72-/H+ MUST distill to remove aldehyde Oxidation
Aldehyde or ketone to alcohol
MnO4-/H+ or Cr2O72-/H+ Oxidation
Alcohol to carboxylic acid
MnO4-/H+ or Cr2O72-/H+ Reflux Oxidation
Amine to ammonium salt
Acid (eg. HCl or H2SO4) Acid/Base
Carboxylic acid to carboxylate salt
Base (eg. NaOH or KOH) Acid/Base
Alcohol to ester
Carboxylic acid + c.H2SO4 + reflux Esterification (Substitution/Condensation)
Carboxylic acid to ester
Alcohol + c.H2SO4 + reflux Esterification (Substitution/Condensatin)
Alcohol to haloalkane
PCl3 or PCl5 or SOCl2 Substitution
Carboxylic acid to acyl chloride
SOCl2 Substitution
Acyl chloride to carboxylic acid
H2O Substitution
Carboxylic acid to amide
c.NH3 or R-NH2 + reflux Substitution
Acyl chloride to amide
c.NH3 or R-NH2 Substitution
Aldehyde to carboxylic acid
Tollen’s, Fehling’s or Benedict’s + heat Oxidation