3.3.14 - Organic Synthesis Flashcards
Alkane → Halogenalkane
State the reaction and the conditions
- Free-radical substitution
- X2, UV light
Halogenalkane → Secondary/tertiary amines, their salts and quaternary ammonium salts
State the reaction and the conditions
- Nucleophilic substitution
- Ammonia, heat
- (not primary halogenalkanes)
Halogenalkane → Primary Amine
State the reaction and the conditions
- Nucleophilic substitution
- Excess ammonia, heat
- (primary halogenalkanes only)
Halogenalkane → Nitrile
State the reaction and the conditions
- Nucleophilic substitution
- KCN(aq), ethanol, reflux
Halogenalkane → Alcohol
State the reaction and the conditions
- Nucleophilic substitution
- Warm, NaOH(aq), reflux
Halogenalkane → Alkene
State the reaction and the conditions
- Elimination
- KOH, ethanol, reflux
Nitrile → Primary Amine
State the reaction and the conditions
- Reduction
- LiAlH4, dry ether, dilute H2SO4
- OR hydrogen gas, platinum/nickel catalyst, high temperature and pressure
Alkene → Halogenalkane
State the reaction and the conditions
- Electrophilic Addition
- HX, 20°C
Alkene → Dibromoalkane
State the reaction and the conditions
- Electrophilic addition
- Br2, 20°C
- (test for unsaturation)
Alkene → Alcohol
State the reaction and the conditions
- Hydrolysis
- H3PO4 catalyst, steam, 300°C, 60 atm
- Electrophilic addition
- H2O, H2SO4 catalyst
Alcohol → Alkene
State the reaction and the conditions
- Elimination
- conc H2SO4, reflux
Alcohol → Carboxylic Acid
State the reaction and the conditions
- Oxidation
- K2Cr2O7, H2SO4, relfux
- (primary alcohols only)
Alcohol → Aldehyde/ketone
State the reaction and the conditions
- Oxidation
- K2Cr2O7, H2SO4, heat in distillation apparatus
Aldehyde/ketone → Alcohol
State the reaction and the conditions
- Reduction/nucleophilic addition
- NaBH4 in water with methanol
Aldehyde/ketone → Hydroxynitrile
State the reaction and the conditions
- Nucleophilic addition
- KCN(aq), H2SO4, 20°C
Carboxylic Acid → Ester
State the reaction and the conditions
- Esterification
- alcohol, conc. H2SO4 catalyst, heat
Ester → Carboxylic Acid
State the reaction and the conditions
- Hydrolysis
- dilute H2SO4 catalyst, H2O, reflux
- OR dilute NaOH(aq), reflux
Acyl Chloride / Acid Anhydride → Carboxylic Acid
State the reaction and the conditions
- Nucleophilic Addition-Elimination
- H2O, 20°C
Acyl Chloride / Acid Anhydride → Ester
State the reaction and the conditions
- Nucleophilic Addition-Elimination
- Alcohol, 20°C
Acyl Chloride / Acid Anhydride → Primary Amine
State the reaction and the conditions
- Nucleophilic Addition-Elimination
- NH3, 20°C
Acyl Chloride / Acid Anhydride → N-Substituted Amide
State the reaction and the conditions
- Nucleophilic Addition-Elimination
- Amine, 20°C
State the reaction and conditions
State the reaction and conditions
State the reaction and conditions
State the conditions
State how chemists design synthesis routes to be safe
Chemists try designing routes that use non-hazardous starting materials to limit the potential for accidents and environmental damage
State how chemists design synthesis routes to be less wasteful
- Use processes with high atom economies and high percentages yields
- Waste can be reduced by designing synthesis routes that have as few steps as possible
Why are processes with high atom economies and high percentages yields preferred?
∵ they convert more of starting material into useful products
Give an example of how you can reduce both hazards associated with process and amount of waste created by a synthesis route
Avoiding solvents
Explain how avoiding solvents reduces hazards
Solvents are often flammable and toxic so pose safety risks
Explain how avoiding solvents reduces waste
If solvent has to be disposed after reaction is complete = lots of waste
