Chapter 28 ORGANIC SYNTHESIS

• Alkane $\rightarrow$Haloalkane?


  Halogen, UV light
• Haloalkane$\rightarrow$Alcohol?


  NaOH(aq)
• Alcohol$\rightarrow$Haloalkane?


  Sodium halide, $H_2SO_4$
• Alcohol$\rightarrow$Aldehyde?


  Potassium dichromate, $H_2SO_4$, distillation
• Aldehyde$\rightarrow$Alcohol?


  $NaBH_4$
• Aldehyde$\rightarrow$Carboxylic Acid?


  Potassium dichromate, $H_2SO_4$, relfux
• Carboxylic Acid$\rightarrow$Acyl Chloride?


  $SOCl_2$
• Acyl Chloride$\rightarrow$Carboxylic Acid?


  $H_2O$
• Acyl Chloride$\rightarrow$Primary amide?


  $NH_3$
• Acyl Chloride$\rightarrow$Secondary Amide?


  Primary amine
• Acyl Chloride$\rightarrow$Ester?


  Alcohol
• Ester$\rightarrow$Carboxylate?


  $OH^-$,heat
• Alcohol$\rightarrow$Ester?


  Carboxylic Acid, conc.$H_2SO_4$ OR acid anhydride
• Carboxylic Acid$\rightarrow$Ester?


  Alcohol, conc.$H_2SO_4$
• Ester$\rightarrow$Carboxylic Acid?


  Dilute acid, heat
• Primary Alcohol$\rightarrow$Carboxylic Acid?


  Potassium dichromate, $H_2SO_4$, reflux
• Secondary Alcohol$\rightarrow$Ketone?


  Potassium dichromate, $H_2SO_4$, reflux
• Ketone$\rightarrow$Secondary Alcohol?


  $NaBH_4$
• Ketone$\rightarrow$Hydroxynitrile?


  $NaCN(aq)$,$H^+$$(aq)$
• Aldehyde$\rightarrow$Hydroxynitrile?


  $NaCN(aq),\ H^+$$(aq)$
• Hydroxynitrile$\rightarrow$Carboxylic Acid?


  $H_2O,\ HCl$, heat
• Hydroxynitrile$\rightarrow$Amine?


  $H_2,\ Ni$
• Nitrile$\rightarrow$Amine?


  $H_2,\ Ni$
• Nitrile$\rightarrow$Carboxylic Acid?


  $H_2O,\ HCl$, heat
• Haloalkane$\rightarrow$Amine?


  $NH_3$, ethanol
• Haloalkane$\rightarrow$Nitrile?


  $CN^-$, ethanol
• Alcohol$\rightarrow$Alkene?


  $H_3PO_4,\ H_2SO_4$, heat
• Alkene$\rightarrow$Alcohol?


  $H_2O$(steam), $H_3PO_4$
• Alkene$\rightarrow$Haloalkane?


  Hydrogen halide
• Alkene$\rightarrow$Alkane?


  $H_2,\ Ni$