Organic synthesis Flashcards
Alkane to Halogenoalkane
Mechanism: Free radical sub
Reagent(s): X₂
Conditions: UV light
Halogenoalkane to alkene
Mechanism: elimination
Reagent(s): KOH or NaOH
Conditions: ethanolic. heat under reflux
alkene to halogenoalkane
Mechanism: e- addition
Reagent(s): HBr or HCl
Conditions: room temp
alkene to dihalogenoalkane
Mechanism: e- addition
Reagent(s): Br₂ or Cl₂
Conditions: room temp
Dihalogenoalkane to Diol
Mechanism: Nucleophilic sub
Reagent(s): KOH
Conditions: (aq) heat under reflux
alkene to poly(alkene)
Conditions: high pressure catalyst
Halogenoalkane to nitrile
Mechanism: Nucleophilic sub
Reagent(s): KCN in ethanol/ water mixture
Conditions: heat under reflux
Nitrile to primary amine
reduction:
LiALH4 dry ether
OR
2H₂ + Ni cat high temp and pressure
Primary amine to secondary, tertiary or quaternary ammonium salt
Mechanism: Nucleophilic sub
Reagent(s): 1y amine
Conditions:
excess Haloalkane = 4y main product
Halogenoalkane to primary amine
Mechanism: Nucleophilic sub
Reagent(s): alcoholic excess NH3
Conditions: heat under pressure
Halogenoalkane to alcohol
Mechanism: Nucleophilic sub
Reagent(s): NaOH or KOH (aq)
Conditions: heat under reflux
alkene to alcohol
Mechanism: e- addition (hydration)
Reagent(s): conc H2SO4 + steam
Conditions: (aq) 300C and high pressure 70 atm
alcohol to alkene
Mechanism: elimination (dehydration)
Reagent(s): excess hot conc H2SO4, hot Al2O3 cat (lab)
Conditions: 600K
1y alcohol to aldehyde
oxidation:
Reagent(s): Na2Cr2O7/H+
Conditions: heat
2y alcohol to ketone
oxidation
Reagent(s): Na2Cr2O7/H+
Conditions: heat
aldehyde to 1y alcohol
Mechanism: Nucleophilic addition
Reagent(s): NaBH4
Conditions: room temp
ketone to 2y alcohol
Mechanism: Nucleophilic addition
Reagent(s): NaBH4
Conditions: room temp
aldehyde or ketone to hydroxynitrile
Mechanism: Nucleophilic addition
Reagent(s): KCN or HCN + H2SO4
Conditions: room temp
aldehyde to carboxylic acid
oxidation
Reagent(s): excess oxidising agent, Na2Cr2O7/H+
Conditions: heat under reflux
alcohol to ester
esterification:
Reagent(s): carboxylic acid and H2SO4
Conditions: heat
carboxylic acid to ester
esterification:
Reagent(s): alcohol + H2SO4
Conditions: Heat
ester to carboxylic acid
Reagent(s): dilute H2SO4 catalyst + H2O
Conditions: reflux
primary amine to secondary amide
Mechanism: Nucleophilic addition
Reagent(s): acyl chloride
Conditions: room temp
secondary amide to acyl chloride or acid anhydride
Mechanism: Nucleophilic add elim
Reagent(s): primary amine
Conditions: room temp
acyl chloride or acid anhydride to carboxylic acid
Mechanism: Nucleophilic add elim
Reagent(s): H2O
Conditions: room temp
acyl chloride or acid anhydride to N-substituted amide
Mechanism: Nucleophilic add elim
Reagent(s): amine
Conditions: room temp
acyl chloride or acid anhydride to primary amide
Mechanism: Nucleophilic add elim
Reagent(s): NH3
Conditions: room temp
Benzene to Nitrobenzene
Mechanism: e- sub
Reagent(s): HNO3 + H2SO4
eqn for formation of nitronium electrophile
HNO3 + 2H2SO4 –> NO2+ + 2HSO4- + H3O+
Benzene to phenyl ethanone
Mechanism: e- sub
Reagent(s): Acyl chloride + ALCl3 cat
eqn for formation of acylium electrophile
AlCl3 + CH3COCl –> [CH3CO]+ + [AlCl4]-
Nitrobenzene to phenyl amine
reduction
Reagent(s): Sn + conc HCl then NaOH
Phenylamine to N-methyl benzenamine
Mechanism: Nucleophilic sub
Reagent(s): CH3Cl
N-methyl benzenamine to N-phenyl ethanomide
Mechanism: Nu add elim
Reagent(s): CH3COCl
Mechanism: Nu add
Reagent(s):
reduction
Reagent(s): LiALH4 OR 2H2 + Ni cat
Mechanism: Nu add
Reagent(s): NaBH4 (reduction)
esterification:
Reagent(s): H2SO4 + CH3COOH
Conditions: heat
