Organic Routes

• alkane -> haloalkane


  halogen, UV light, rad sub

  
• alkene -> alkane


  H2, Ni

  
• haloalkane -> nitrile


  NaCN, ethanol, reflux

  
• haloalkane -> amine


  NH3, ethanol, nucleophilic substitution

  
• alcohol -> alkene


  conc H2SO4, heat

  
• Alkene -> alcohol


  Steam, H3PO4, nucleophilic addition

  
• haloalkane -> alcohol


  NaOH, reflux

  
• alcohol -> haloalkane


  Sodium halide, H2SO4, reflux, nucleophilic substitution

  
• nitrile -> amine


  H2, Ni, reduction

  
• alcohol -> ester


  Carboxylic acid with conc H2SO4 or acid anhydride

  
• primary alcohol -> aldehyde

  K2Cr2O7, H2SO4, distil

  
• primary alcohol -> carboxylic acid

  K2Cr2O7, H2SO4, reflux

  
• aldehyde -> primary alcohol

  NaBH4, reduction, nucleophilic addition

  
• secondary alcohol -> ketone

  K2Cr2O7, H2SO4, reflux

  
• ketone -> secondary alcohol

  NaBH4, reduction, nucleophilic addition

  
• aldehyde -> hydroxynitrile


  NaCN, H+, nucleophilic addition
• ketone -> hydroxynitrile


  NaCN, H+, nucleophilic addition
• hydroxynitrile -> amine


  H2, Ni
• aldehyde -> carboxylic acid

  K2Cr2O7, H2SO4, reflux
• carboxylic acid -> acyl chloride

  SOCl2
• acyl chloride -> carboxylic acid

  H2O, hydrolysis
• nitrile -> carboxylic acid

  H2O, HCl, heat
• hydroxynitrile -> carboxylic acid

  H2O, HCl, heat
• carboxylic acid -> ester

  Alcohol, conc H2SO4, heat, esterification
• ester -> carboxylic acid

  dilute acid, heat, reflux, saphonification
• ester -> carboxylate


  OH-, heat, alkaline hydrolysis
• acyl chloride -> ester

  Alcohol, room temp, nucleophilic addition
• acyl chloride -> primary amide

  NH3, room temp, nucleophilic addition
• acyl chloride -> secondary amide

  primary amine, room temperature, nucleophilic addition
• Nitrobenzene -> phenylamine


  Sn, conc HCl, reflux

  
• Phenyl amine -> 2,4,6-tribromophenylamine

  Br2, electrophilic substitution

  
• benzene -> nitrobenzene


  Conc HNO3, conc H2SO4, warmed

  
• benzene -> bromobenzene


  Br2/AlBr3 or Fe or FeBr3
• benzene -> methylbenzene


  CH3Cl, AlCl3

  
• benzene -> chlorobenzene


  Cl2 / AlCl3 or Fe or FeCl3

  
• benzene -> phenylethanone


  CH3COCl, AlCl3, acylation

  
• phenylethanone -> phenylethanol


  NaBH4, reduction, nucleophilic addition

  
• phenol -> bromophenol


  bromine gas, AlCl3