CM3221

Ketone/Aldehyde

  1. Acid Chloride using R(2)CuLi
  1. DMF to make aldehydes by introducing R group
  1. Nitrile with R1 attached and R2 introduced to form enamine

Reduction Amination

  1. Amide (LiAlH4)
  1. Enamine/imine (NaB(CN)H3), NaB(OAc)3H)
  1. Azide (NaBH4)
  1. Cyanide (CH2NH2) (H2, Raney Ni)

Alcohols

  1. Grignard Reagent
  1. Epoxides (Made from Alkenes or Sulfur Yilid, Me2S=CH2)

Carboxylic Acids

  1. CO2 plus Grignard Reagent
  1. Cynaide followed by hydrolysis

Sulfides

RSH (using thiourea and react with R-Br, follow by NaOH, H2O to release RSH)

Mannich

Double Bond with one Ester group and one Electron donating Group

Knoevenagel Reaction Use 1,3 dicarbonyl plus respective aldehyde/ketones

  1. CH2O +R2NH to form enamine with H+. 2. MeI to form good leaving group 3. Base to form double bond

1,2 difunctional Compounds

  1. Using Nitro Alkanes

Amino Acids (ketone and amine to form enamine and then attack via CN and hydrolysis to form COOH

Alkene Synthesis

  1. See if can add OH group to become carbonyl reaction
  1. Use Wittig