Organic Synthesis Flashcards
Alkene to Alkane
H2
Nickel Catalyst
150°C
Alkane to Halogenoalkane
UV light
Hydrogen Halide
Free Radical Substitution
Alkene to Halogenoalkane
Hydrogen Halide
Halogenoalkane to Alkene
Potassium Hydroxide
Ethanol
Heat
Alkene to Alcohol
H2O (steam)
300°C
60-70 atm
Phosphoric (V) acid catalyst
Alcohol to Alkene
Sulfuric Acid
High temperature
Halogenoalkane to Alcohol
Potassium Hydroxide
Reflux
Alcohol to Halogenoalkane
PCl5/HCl
KBr - Reflux
HI
Halogenoalkane to Amine
Conc Ammonia (NH3)
Ethanol
Sealed Tube
Primary Amine to Secondary/Tertiary Amine
React with a halogenoalkane
Amine to Polyamide
Dicarboxylic acid and diamine
Amine to Amide
Acyl Chloride
Ammonia
Alcohol to Ketone
Potassium Dichromate
Reflux
Ketone to Secondary Alcohol
LiAlH4
Dry Ether
Primary Alcohol to Aldehyde
Potassium Dichromate
Reflux and Distill product off
Aldehyde to Primary Alcohol
LiAlH4
Dry Ether
Alcohol/Aldehyde to Carboxylic Acid
Potassium Dichromate
Reflux and Distill off later
Carboxylic Acid to Alcohol
LiAlH4
Carboxylic Acid to Ester
Conc Sulfuric Acid
Alcohol
Warm in a bath
Alcohol to Ester
Acyl Chloride
Halogenoalkane to Nitrile
Potassium Cyanide
Reflux
Nitrile to Carboxylic Acid
HCl and water
NaOH and water
Nitrile to Amine
LiAlH4
Dry ether
Nitrile to Amide
H2O
Amide to Nitrile
Phosphor Oxide P4O10
Grinards Reagent
Used to extend carbon chain
Preparation
Halogenoalkane is dissolved in dry ether and reacted with magnesium
CH3CH2Br + Mg → CH3CH2MgBr
Reactions
Methanal produces a primary alcohol
CH3CH2MgBr + HCHO → CH3CH2CH2OH + Mg(OH)Br
Longer aldehydes produce a secondary alcohol
CH3CH2MgBr + CH3CHO → CH3CH2CH(OH)CH3 + Mg(OH)Br
Ketones produce a tertiary alcohol
Ch3CH2MgBr + CH3COCH3 → CH3CH2C(CH3)(OH)CH3 + Mg(OH)Br
Carbon dioxide produces carboxylic acids
CH3CH2MgBr + CO2 → CH3CH2COOH + Mg(OH)
Refluxing
When you want to ensure that none of the products can escape from the reflux vessel
All gases are condensed back into a liquid and run back into pear shaped flask
Water in at the bottom
Water out at the top
Ketone to HydroxyNitrile
Hydrogen Cyanide
Potassium Cyanide and Sulfuric Acid
Aldehyde to Hydroxynitrile
Hydrogen Cyanide
Potassium Cyanide and Sulfuric Acid
Ester to Carboxylic Acid
Water with Dilute Acid
Reflux
Acyl Chloride to Ester
Cold Ethanol
Acyl Chloride to Amide
Concentrated Ammonia
Filtration
If the product is a solid, it can be separated by filtration using a buchner finnel with suction from a water pump
Steam Distillation
Distillation with steam at 100°C allows for the separation of compounds that decompose if heated at their boiling temperatures
Only works for compounds that do not mix with water
Leaves behind reagents and products that are soluble in water
Solvent Extraction
- add mixture to separating funnel and mix with water
- add organic solvent and shake
- add salt to organic product
- open tap and separate
- remove water by adding anhydrous salt such as calcium chloride
Recrystallisation
- dissolve solid in minimum volume of hot solvent
- filter through fluted paper and funnel
- cool to allow crystals to form
- filter using buchner funnel
- dry
Washing and Drying to Purify Organic Liquids
- wash with water
- dry
- wash again
- leave in warm place or mix with a drying agent
Fractional Distillation
- column packed with glass beads to give maximum surface area
- there is a vent in system to prevent pressure build up
- flask may need to be surrounded with ice if liquid has a low boiling point
- mixture heated so that the thermometer is at the temperature of the boiling point
