Organic Synthesis routes

• Haloalkane (R-X) → Nitrile (R-C≡N)

  KCN (potassium cyanide) (or NaCN) in ethanol

  
  

  Nucleophilic Substitution
• Haloalkane (R-X) → Amine (R-NH₂)

  NH₃ (ammonia) in ethanol
• Carboxylic acid (R-COOH) → Ester (R-COO-R')

  Alcohol (R'-OH)

  concentrated H₂SO₄ catalyst

  
  

  Esterification
• Primary Alcohol (R-CH₂OH) → Aldehyde (R-CHO)

  Distil with K₂Cr₂O₇/H₂SO₄ (acidified potassium dichromate)
• Primary Alcohol (R-CH₂OH) → Carboxylic acid (R-COOH)

  Reflux with K₂Cr₂O₇/H₂SO₄ (acidified potassium dichromate)

  Uses two molecules of oxidising agent ([O]), produces one molecule of H₂O
• Secondary Alcohol (R-CH(OH)-R') → Ketone (R-C(O)-R')

  Reflux with K₂Cr₂O₇/H₂SO₄ (acidified potassium dichromate)

  Byproduct: H₂O
• Alkene → Alkane


  H₂

  Ni catalyst

  150⁰C
• Nitrile (R-C≡N) → Amine (R-NH₂)

  H₂

  Ni catalyst

  Room temperature
• Alkane → Haloalkane (R-X)

  Halogen (X₂)

  Ultraviolet light (UV)

  
  

  Free radical substitution
• Alcohol (R-CH₂OH) → Ester (R'-COO-R)

  Carboxylic acid (R'-COOH)/ concentrated H₂SO₄ catalyst

  Byproduct: H₂O

  OR

  Acyl chloride (R'-COCl) (no catalyst)

  Byproduct: HCl

  OR

  Acid anhydride ((R'-COO)₂O)or(R'-COOCO-R') (no catalyst)

  Byproduct: Carboxylic acid (R'-COOH)

  
  

  Esterification
• Carboxylic acid (R-COOH) → Acyl chloride (R-COCl)

  SOCl₂ (Thionyl chloride)
• Acyl chloride (R-COCl) → Carboxylic acid (R-COOH)

  H₂O

  Room temperature

  
  

  Hydrolysis
• Alkene → Haloalkane (R-X)

  Hydrogen halide (HX)

  Room temperature

  
  

  Electrophilic addition
• Alkene → Dihaloalkane (e.g. CH₃CHXCHXCH₃)

  Halogen (X₂)

  Room temperature

  
  

  Electrophilic addition
• Alcohol (R-OH) → Haloalkane (R-X)

  Sodium halide (NaX) / conc. H₂SO₄ (this forms HX in situ)

  Heat under reflux
• Aldehyde (R-CHO) → Hydroxynitrile (R-CH(OH)(C≡N))

  Ketone (R-CO-R') → Hydroxynitrile

  (R-C(OH)(C≡N)-R')

  NaCN (sodium cyanide)/ H⁺ (forms HCN in situ)

  
  

  Nucleophilic addition
• Acyl chloride (R-COCl) → Pimary amide (R-C(O)NH₂)

  NH₃ (ammonia)
• Acyl chloride (R-COCl) → Secondary amide (R-C(O)NH-R')

  Primary amine (R-NH₂)
• Alkene → Alcohol (R-OH)

  H₂O (steam) / H₃PO₄ (phosphoric acid)

  
  

  Hydration
• Aldehyde (R-CHO) → Primary alcohol (R-CH₂OH)

  Ketone (R-CO-R') → Secondary alcohol (R-CH(OH)-R')

  NaBH₄ / H₂O (aqueous sodium tetrahydridoborate)

  
  

  Reduction

  Two molecules of reducing agent ([H]) are used in the reaction
• Alcohol (R-OH) → Alkene

  Concentrated H₂SO₄ or H₃PO₄ (phosphoric acid)

  Heat

  
  

  Elimination of water/ Dehydration
• Nitrile (R-C≡N) → Carboxylic acid (R-COOH)

  H+(aq)

  Heat

  
  

  Hydrolysis
• Ester (R-COO-R')→ Carboxylic acid (R-COOH) + Alcohol (R'-OH)

  Hot aqueous (dilute) acid

  
  

  Acid hydrolysis
• Ester (R-COO-R')→ Sodium Carboxylate salt (R-COO⁻Na⁺)+ Alcohol (R'-OH)

  NaOH(aq) (aqueous sodium hydroxide)

  Heat

  
  

  Alkaline hydrolysis
• Haloalkane (R-X) → Alcohol (R-OH)

  NaOH(aq) (aqueous sodium hydroxide)

  Heat

  
  

  Nucleophilic substitution
• Benzene (C₆H₆) → Methylbenzene (Toluene) (C₆H₅CH₃)

  CH₃Cl (chloromethane)

  AlCl₃ (Halogen carrier)

  
  

  Friedel-Crafts alkylation

  Electrophilic substitution
• Benzene (C₆H₆) → Phenylethanone (C₆H₅COCH₃)

  CH₃COCl (ethanoyl chloride)

  AlCl₃ (Halogen carrier)

  
  

  Friedel-Crafts acylation

  Electrophilic substitution
• Phenylethanone (C₆H₅COCH₃) → 1-phenylethanol (CH₃CH(C₆H₅)OH)

  NaBH₄ / H₂O (aqueous sodium tetrahydridoborate)

  
  

  Reduction

  Two molecules of reducing agent ([H]) are used in the reaction
• Benzene (C₆H₆) → Chlorobenzene (C₆H₅Cl)

  Cl₂ (Chlorine)

  AlCl₃ (Halogen carrier)

  
  

  Chlorination

  Electrophilic substitution
• Benzene (C₆H₆) → Bromobenzene (C₆H₅Br)

  Br₂ (Bromine)

  FeBr₃ (Halogen carrier)

  
  

  Bromination

  Electrophilic substitution
• Benzene (C₆H₆) → Nitrobenzene (C₆H₅NO₂)

  HNO₃ (Nitric acid)

  H₂SO₄ (Sulphuric acid)

  Forms NO₂⁺ in situ

  
  

  Nitration

  Electrophilic substitution
• Nitrobenzene (C₆H₅NO₂)→ Phenylamine (Aniline)(C₆H₅NH₂)

  Sn (Tin) / HCl, (then NaOH)

  
  

  Reduction
• Phenylamine (Aniline)(C₆H₅NH₃) → (2,4,6-tribromophenyl)amine ((C₆H₂Br₃)NH₂)

  Br₂ (Bromine)

  
  

  No halogen carrier required

  Electrophilic substitution
• Phenol (C₆H₅OH) → Nitrophenol (HOC₆H₅(NO₂))

  HNO₃ (Nitric acid)

  
  

  Nitration

  Electrophilic substitution
• Phenol (C₆H₅OH) → Sodium phenoxide (C₆H₅O⁻Na⁺)

  NaOH(aq)

  
  

  Neutralisation
• Phenol (C₆H₅OH) → 2,4,6-Tribromophenol (C₆H₂Br₃OH)

  Br₂ (Bromine)

  
  

  Bromination

  Electrophilic substitution