A-Level Synthetic routes

• Primary alcohol → Aldehyde

  K₂Cr₂O₇ (acidified with H₂SO₄) ( [O] )Distil
• Carboxylic Acid → Aldehyde

  No
• Carboxylic Acid → Alcohol

  No
• Primary alcohol → Carboxylic acid


  K₂Cr₂O₇ (acidified with H₂SO₄) ( 2[O] )Heat under reflux
• Secondary alcohol → Ketone


  K₂Cr₂O₇ (acidified with H₂SO₄) ( [O] )Heat under reflux
• Alcohol → Alkene


  concentrated H3PO4 or H2SO4

  Heat
• Alkene → Alcohol


  H2O (steam) / H3PO4 catalyst

  
• Alkene → Alkane


  H2 Nickel catalyst 150 degrees

  
• Alkane → Haloalkane


  Halogen UV light

  
• Haloalkane → Alcohol


  aqueous NaOH

  heat under reflux
• Alcohol → Haloalkane


  Sodium halide

  H2SO4

  heat under reflux

  
• Alkene → Haloalkane


  Hydrogen halide

  
• Aldehyde → Alcohol


  NaBH4/H2O (2[H])
• Ketone → Alcohol


  NaBH4/H2O (2[H])

  
• Aldehyde → Hydroxynitrile


  NaCN(aq)/H2SO4(aq) which then gives HCN

  
• Carboxylic Acid + Alcohol → ? + ?

  Ester + Water (esterification)Heat with Concentrated H2SO4

  
• (same) Carboxylic Acid + Carboxylic Acid → ? + ?(condensation reaction)


  Acid Anhydride + Water

  
• Ester + Water ⇌ ? + ?(Acid Hydrolysis)

  Carboxylic Acid + Alcohol

  Hot Aqueous Acid

  Heat under reflux

  
• Ester + OH-(aq) → ? + ?(Alkaline Hydrolysis)

  Carboxylate ion + Alcohol

  Hot Aqueous OH- ions

  Heat under reflux

  
• Carboxylic Acid + SOCl2 → ? + ? + ?


  Acyl Chloride + SO2 (g) + HCl (g)

  In a fume cupboard

  
• Acyl Chloride + Alcohol → ? + ?

  Ester + HCl

  
• Acyl Chloride + Phenol → ? + ?

  Phenyl Ester + HCl

  
• Acyl Chloride + Water → ? + ?

  Carboxylic Acid + HCl

  
• Acid Anhydride + Alcohol → ? + ?


  Ester + Carboxylic Acid

  
• Acyl Chloride + Ammonia → ? + ?

  Primary Amide + NH4Cl

  
• Acyl Chloride + Primary Amine → ? + ?

  Secondary Amide + HCl

  
• Amine + Acid (e.g. HCl or H2SO4) → ?

  Ammonium Salt
• Haloalkane → Primary Amine(2 Step)


  Add NH3 (Ethanolic ammonia) → Ammonium Salt

  Ammonium Salt + Aqueous Alkali → Primary Amine

  Ethanol Solvent

  Excess Ammonia

  under reflux
• Haloalkane → Secondary Amine(2 Step)

  Add Primary Amine → Ammonium Salt

  Ammonium Salt + NaOH → Secondary Amine + Water + NaX(Salt)
• Haloalkane → Tertiary Amine(2 Step)

  Add Secondary Amine → Ammonium Salt

  Ammonium Salt + NaOH → Tertiary Amine + Water + NaX(Salt)
• Nitrobenzene → Phenylamine


  Heated under reflux with Tin (Sn) + HCl → Phenylammonium Chloride

  Phenylammonium Chloride + excess NaOH → Phenylamine

  
• Amino acid + Acid (HCl) → ?

  Ammonium Salt

  NH2 group on amino acid becomes NH3+ since it is basic (accepts proton from the acid)

  
• Amino acid + Aqueous Alkali (NaOH) → ? + ?

  Salt + Water

  carboxylic acid group is acidic hence why it becomes COO-

  
• Amino Acid + Excess Alcohol + H2SO4 → ? + ?

  Ester + Water

  NH2 is protonated by the acid

  
• Amide + Water → ? + ?(Acid hydrolysis)

  Carboxylic Acid + Ammonium Salt

  Aqueous HCl and reflux

  
• Amide + Water → ? + ?(Alkali hydrolysis)

  (Sodium) Salt + Amine

  Aqueous NaOH and reflux

  
• Benzene → Nitrobenzene(Nitration)


  Concentrated HNO3

  Concentrated H2SO4

  50 degrees Celsius

  
• Benzene + (Br2/FeBr3 or Cl2/AlCl3)(Halogenation)

  Generate electrophile e.g. Cl2 + AlCl3 → Cl+ + AlCl4-

  
• Benzene(Alkylation)

  Use Haloalkane and AlCl3

  attaches an alkyl group to the benzene ring with HCl as a by product

  
• Benzene → Aromatic Ketone(Acylation)


  Use Acylchloride and AlCl3 and HCl as a byproduct