Synthetic routes Flashcards
Benzene to Nitrobenzene
Reaction: Nitration
Mechanism: Electrophilic Substitution
Conditions: 1- Multiple Nitration Heat above 55 c
2- conc H2SO4 (catalyst)
3- conc HNO3
4- Mononitration Below 55 c kk
Benzene to Phenylketone
Reaction: Actylation
Mechanism: Electrophilic Substitution
Conditions: 1- AlCl3 (catalyst)
2-Acyl chloride
3-Dry ether
4-Heat Under RefluxNitrobenzene to Phenylamine
Reaction: Reduction
Conditions: 1- conc HCl (catalyst/Reducing agent)
2- Sn/Tin (catalyst/Reducing agent )
3-Heat Under Reflux
4- aqueous NaOH
Phenylamine to N-Phenylethanamide
Mechanism: Nucleophilic Addition-Elimination
Conditions: 1- CH3COCl
2- 25 c
Alkane to Halogenoalkane
Reaction: Photochemical
Mechanism: Free Radical Substitution
Conditions: 1- UV Light
2- Halogen (X2)
Halogenoalkane to Alcohol
Mechanism: Nucleophilic Substitution
Conditions: 1- Warm aqueous NaOH
2- Heat Under Reflux
Halogenoalkane to Nitrile
Mechanism: Nucleophilic Substitution
Conditions: 1- aqueous KCN
2- Ethanol
3- Heat Under Reflux
Halogenoalkane to Primary Amine
Mechanism: Nucleophilic Substitution
Conditions: 1- warm conc excess ethanolic NH3
2- Sealed Tube
Increase conc of warm excess ethanolic NH3 relative to Conc of Halogenoalkane so less likely chance halogenoalkane will react with an newly produced amine and more likely tor react with NH3
Primary Amine to Secondary Amine /Tertiary Amine/ Quaternary Ammonium Salts
Mechanism: Nucleophilic Substitution
Conditions: 1- warm conc excess ethanolic NH3
2- Sealed Tube
Decrease conc of warm excess ethanolic NH3 relative to Conc of Halogenoalkane so more likely chance halogenoalkane will react with an newly produced amine and less likely to react with NH3
Nitrile to Primary Amine
Reaction: Reduction
IN LAB
Conditions 1-LiAlH4 (reducing agent)
2-dry ether
3- dilute H2SO4 (Catalyst)
INDUSTRY-Catalytic Hydrogenation
Conditions: 1- Ni (catalyst)
2-Hydrogen gas
3- High Temp
4- High pressure
Halogenoalkane to Alkene
Reaction: Dehydration + condensation
Mechanism: Elimination
Conditions: 1- conc NaOH/KOH
2- Warm Ethanol
3-Heat Under RefluxAlkene to Halogenoalkane
Mechanism: Electrophilic Addition
Conditions: 1- HX/X2
2- 25 c
Alkene to Dibromoalkane
Reaction: Oxidation
Mechanism: Electrophilic addition
Conditions: 1-Br2/bromine water
2- 25 c
Alkene to Alcohol
Reaction: Hydration+ Hydrolysis +
Mechanism: Electrophilic Addition
Conditions: 1- H3PO4 (catalyst)
2-steam
3-300 c
4-60 atmGlucose to Alcohol
Reaction: Fermentation of Glucose/ Exothermic
Conditions: 1- Yeast
2- 30-40 c
3- Anaerobic
Alcohol to Alkene
Reaction: Dehydration + Condensation +
Mechanism: Elimination
Conditions: 1-Hot/Heat
2-excess conc H2SO4 (catalyst)
Primary Alcohol to Aldehyde
Reaction: Oxidation
Conditions: 1-Heat Under DISTILLATION
2-acidified K2Cr2O7 (oxidising agent)
3-dilute H2SO4
Primary Alcohol to Carboxylic Acid
Reaction: Oxidation
Conditions: 1-Heat Under REFLUX
2-acidified K2Cr2O7 (oxidising agent)
3-dilute H2SO4
Secondary Alcohol to Ketone
Reaction: Oxidation
Conditions: 1-Heat Under Reflux
2-Acidified K2Cr2O7 (oxidising agent)
3-dilute H2SO4
Aldehyde to Primary Alcohol
Reaction: Reduction
Mechanism: Nucleophilic Addition
conditions: 1-NaBH4 (reducing agent)
2-Water
3-MethanolKetone to Secondary Alcohol
Reaction: Reduction
Mechanism: Nucleophilic Addition
Conditions: 1-NaBH4 (reducing agent)
2-Water
3-MethanolAldehyde to Carboxylic Acid
Reaction: Oxidation
Conditions: 1-Heat Under Reflux
2-acidified K2Cr2O7
3-dilute H2SO4
Aldehyde to Hydroxynitrile
Mechanism: Nucelophilic Addition
Conditions: 1-acidified aqeuous KCN
2-dilute H2SO4
3-25 c
Ketone to Hydroxynitrile
Mechanism: Nucleophilic Addition
Conditions: 1- acidified aqueous KCN
2-dilute H2SO4
3-25 c
Carboxylic Acid to Ester
Reaction: Esterfication/Condensation
Conditions: 1-Heat Under Reflux
2-Alcohol
3-conc H2SO4 (Catalyst)
Ester to Carboxylic Acid
Reaction: Acid Hydrolysis
Conditions: 1-Heat under Reflux
2-dilute H2SO4 (catalyst)
Reaction: Base Hydrolysis
Conditions: 1-Heat Under Reflux
2-dilute aqueous NaOH (catalyst)
Biodiesel (Methyl Esters)
Reaction: Base Hydrolysis
1-KOH (Catalyst)
2-methanol
Acyl Chloride to Carboxylic Acid
Reaction:
Mechanism: Nucleophilic Addition-Elimination
Conditions: 1- water
2- 25 c
Acyl Chloride to Ester
Mechanism: Nucleophilic Addition-Elimination
Conditions: 1- alcohol
2- 25 c
Acyl Chloride to Primary amide
Mechanism: Nucleophilic Addition-Elimination
Conditions: 1- NH3
2- 25 c
Acyl Chloride to N-Substituted Amide
Mechanism: Nucleophilic Addition-Elimination
Conditions: 1- amine
2- 25 c
Acid Anhydride to Carboxylic Acid
Reactions: Hydrolysis
Conditions: 1- Water
2- 25 c
Acid Anhydride to Ester
Reactions: Acetylation
Conditions: 1- Alcohol
2- 25 c
Acid Anhydride to Primary Amide
Reaction: Acetylation
Conditions: 1- NH3
2- 25 c
Acid Anhydride to N-Substituted Amide
Reaction: Acetylation
Conditions: 1-Amine
2- 25 c
Alkene to Alcohol with Alkyl hydrogensulfate intermediate
Reaction: Hydration + Hydrolysis
Mechanism: Electrophilic Additions
Conditions:STEP 1-conc H2SO4 (catalyst)
STEP 2-cold water + warm up
Hydrocarbons to alkenes
Thermal Cracking
1-High Temp
2-High Pressure
Hydrocarbons to Aromatic Hydrocarbons/Alkanes
Catalytic Cracking
Zeolite Catalyst
1-Slight/Moderate Pressure
2-High Temp
Hydroxynitrile to Carboxylic acid
Reaction: Acid Hydrolysis
Conditions: 1-Heat under Reflux
2-dilute aqueous H2SO4 (catalyst)
Reaction: Base Hydrolysis
Conditions: 1-Heat Under Reflux
2-dilute aqueous NaOH (catalyst)
Advantages of Using Ethanoic Anhydride over Ethanoyl Chloride in making aspirin
1-Cheaper 2-Doesn't produce toxic HCl 3-less corrosive 4-reacts more slowly with water 5-less easily hydrolysed 6-less violent reaction
Advantages of using ethanoyl Chloride over Ethanoic Anhydride in making aspirin
1-faster Rate 2-Not reversible 3-bigger yield 4-purer product 5-no acid catalyst needed
