Intro To Synthesis Flashcards
How to make ethyl ethanoate with only ethanol
-heat under reflux with acidified potassium dichromate to make ethanoic acid
-heat under reflux with conc H2SO4 catalyse
When designing a synthetic pathway what must be considered
-product yield
-reaction set up (catalysts, reagents,conditions)
-process involved (batch or continuous)
-hazards
-costs
-formation of isomers
How to calculate empirical formula from combustion data
Burn in excess oxygen and pass through tube with water absorber (eg anhydrous CaCl2(s) ) and measure change in mass then pass through tube with carbon dioxide absorber (eg CaOH) and measure change in mass
Substance used to absorb water
Calcium chloride
Substance used to absorb carbon dioxide
Calcium hydroxide
How to make alkane into halogenoalkane
UV light and halogen at room temp, free radical substitution
Alkene to alkane
Hydrogen and nickel catalyst at 150C, electrophilic addition
Alkene to halogenoalkane
Hydrogen halide, electrophilic addition
How to make halogenoalkane into alkene
Heat with conc NaOH in ethanol, elimination reaction
Halogenoalkane to amine
Heat with excess concentrated ammonia in sealed tube with ethanol, nucleophilic substitution
Halogenoalkane to nitrile
Heat under reflux with KCN in ethanol, nucleophilic substitution
Nitrile to amine 2 ways
-LiAlH4 in dry ether followed by dilute acid
-hydrogen and platinum catalyst heated to 150C
Reduction
Halogenoalkane to alcohol
Heat with dilute aqueous NaOH, nucleophilic substitution
Alcohol to halogenoalkene
With conc HX/ PCl5
Alcohol into ketone
Heat under reflux with acidified K2Cr2O7, oxidation
Ketone to alcohol
LiAlH4 in dry ether followed by dilute acid, reduction
Alcohol to aldehyde
Heat with acidified K2Cr2O7 and distil product immediately, oxidation
Aldehyde to alcohol
LiAlH4 in dry ether followed by dilute acid, reduction
Ketone/aldehyde to hydroxynitrile
Dilute sulphuric acid and excess KCN, nucleophilic addition
Alkene to dihalogenoalkane
Hydrogen halide
Nitrile to carboxylic acid
Heat under reflux with dilute HCl (aq)/ dilute NaOH (aq) followed by dilute acid, hydrolysis
Alkene into alcohol
Heat with steam and phosphoric acid at 300C and 60atm , hydration
Alcohol to alkene
Heated with excess of concentrated phosphoric acid at 170C, elimination
Carboxylic acid to ester
Heat with concentrated sulfuric acid and alcohol, condensation
Ester to carboxylic acid
Acid hydrolysis, heat under reflux with dilute HCl (aq) / heat under reflux with dilute NaOH (aq) followed by dilute HCl, hydrolysis
Acyl chloride to ester
Alcohol at room temp, nucleophilic addition/elimination
Carboxylic acid to acyl chloride
PCl5 at room temp
Acyl chloride to amide
Concentrated ammonia in water
Aldehyde to carboxylic acid
Heat under reflux with acidified K2Cr2O7, oxidation
Carboxylic acid to aldehyde
Reduce acid to primary alcohol by adding LiAlH4 in dry ether and adding water, then heat with acidified K2Cr2O7 and distil product immediately
