3.14 Organic synthesis
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Features of an ideal synthetic route
• Uses non hazardous reactants • High atom economy and percentage yield • Fewest possible steps • Avoids solvents
Why should solvents be avoided when designing a synthetic route?
• Many solvents are highly flammable or toxic (increased hazards) • Solvents have to be removed • Create a lot of waste
Organic synthesis Acyl chloride / acid anhydride –> Ester
REAGENT: Alcohol CONDITIONS: none TYPE: Nucleophilic addition elimination
Organic synthesis Ester –> Alcohol
REAGENT: H₂SO₄ (aq) OR NaOH (aq) CONDITIONS: Reflux TYPE: Hydrolysis
Organic synthesis Alcohol –> Ester
REAGENT: Carboxylic acid CONDITIONS: Reflux + conc. H₂SO₄ catalyst TYPE: Esterification
Organic synthesis Alcohol –> Ketone
REAGENT: H₂SO₄ and K₂Cr₂O₇ CONDITIONS: Reflux TYPE: Oxidation
Organic synthesis Ketone –> Alcohol
REAGENT: NaBH₄ CONDITIONS: Aqueous TYPE: Nucleophilic addition (reduction)
Organic synthesis Ester –> Carboxylic acid
REAGENT: H₂SO₄ (aq) CONDITIONS: Reflux TYPE: Hydrolysis
Organic synthesis Carboxylic acid –> Ester
REAGENT: Alcohol CONDITIONS: Reflux TYPE: Esterification
Organic synthesis Alcohol –> Aldehyde
REAGENT: H₂SO₄ and K₂Cr₂O₇ CONDITIONS: Immediate distillation TYPE: Oxidation
Organic synthesis Aldehyde –> Alcohol
REAGENT: NaBH₄ CONDITIONS: Aqueous TYPE: Nucleophilic addition (reduction)
Organic synthesis Aldehyde –> Carboxylic acid
REAGENT: H₂SO₄ and K₂Cr₂O₇ CONDITIONS: reflux TYPE: Oxidation
Organic synthesis Alcohol –> Carboxylic acid
REAGENT: H₂SO₄ and K₂Cr₂O₇ CONDITIONS: Reflux TYPE: Oxidation
Organic synthesis Halogenoalkane –> Alcohol
REAGENT: NaOH OR KOH CONDITIONS: Warm + aqueous TYPE: Nucleophilic substitution
Organic synthesis Alkene –> Alcohol
REAGENT: H₂O CONDITIONS: conc. H₃PO₄ catalyst + High temperature and pressure TYPE: Hydration
Organic synthesis Alcohol –> Alkene
REAGENT: conc. H₂SO₄ CONDITIONS: Heat TYPE: Elimination
Organic synthesis Acyl chloride –> Carboxylic acid
REAGENT: H₂O CONDITIONS: none TYPE: Nucleophilic addition elimination
Organic synthesis Acyl chloride –> Primary amide
REAGENT: NH₃ CONDITIONS: none TYPE: Nucleophilic addition elimination
Organic synthesis Halogenoalkane –> Primary amine
REAGENT: Excess NH₃ CONDITIONS: Heat + Ethanolic TYPE: Nucleophilic substitution
Organic synthesis Primary amine –> Secondary amine
REAGENT: RX CONDITIONS: Heat TYPE: Nucleophilic substitution
Organic synthesis Secondary amine –> Tertiary amine
REAGENT: RX CONDITIONS: Heat TYPE: Nucleophilic substitution
Organic synthesis Primary amine –> Secondary amide
REAGENT: Acyl chloride CONDITIONS: none TYPE: Nucleophilic addition-elimination
Organic synthesis Halogenoalkane –> Nitrile
REAGENT: KCN OR NaCN CONDITIONS: Aqueous and ethanolic TYPE: Nucleophilic substition
Organic synthesis Nitrile –> Amine
REAGENT: H₂ CONDITIONS: Ni catalyst + High temperature and pressure TYPE: Reduction