Alkenes

Annotations:

• < HBr, 20 degrees

1. Haloalkane

   Annotations:

   • - STASQAS - ammonia, heat - PA - ammonia and heat - N - KCN, ethanol, reflux  - A - NaOH, ethanol, reflux 
   1. Alcohol
   2. alkane

      Annotations:

      • ¬ Cl2 U.V light
   3. secondary, tertiary amines and their salts and quaternary ammonium salts
   4. primary amine
   5. nitrile

      Annotations:

      • ^ LiAlH4, dilute H2SO4
      1. primary amine
2. Alcohol

   Annotations:

   • ¬ conc. H2SO4, reflux ^ K2Cr2O7, H2SO4, heat in distillation apparatus
   1. Ketone/Aldehyde

      Annotations:

      • <NaBH4 in water with methanol ^ KCN/HCN, H2SO4, 20 degrees  ¬ K2Cr2O7, H2SO4, reflux
      1. hydroxynitrile
      2. Carboxylic acid

         Annotations:

         • < doesn't happen > alcohol, conc. H2SO4 catalyst, heat 
         1. Ester

            Annotations:

            • < Dilute H2SO4 catalyst, H2O, reflux  or Dilute NaOH, reflux
         2. Acyl Chloride

            Annotations:

            • doesn't form a carboxylic acid -To PA - NH3, 20 degrees -To N-SA - amine, 20 degrees -To E - alcohol, 20 degrees
            1. Ester
            2. N-substituted amine
            3. Primary amide
3. Dibromoalkane

   Annotations:

   • Br2, 20 degrees