Organic Synthesis and Analysis Flashcards
Give the mechanism name, reagents and conditions for a reaction to turn a haloalkane into a primary/secondary/tertiary amine or quaternary ammonium salt.
Nucleophilic substitution, excess ammonia, heat.
Give the mechanism name, reagents and conditions for a reaction to turn a haloalkane into a nitrile.
Nucleophilic substitution, aqueous potassium cyanide in ethanolic solution under reflux.
Give the mechanism name, reagents and conditions for a reaction to turn a nitrile into a primary amine.
Reduction, LiAlH4 with dilute sulphuric acid.
Give the mechanism name, reagents and conditions for a reaction to turn an alkane into a haloalkane.
Free radical substitution, Cl2, UV light
Give the mechanism name, reagents and conditions for a reaction to turn a haloalkane into an alkene.
Elimination, NaOH in the presence of ethanol and under reflux.
Give the mechanism name, reagents and conditions for a reaction to turn an alkene into a haloalkane.
Electrophilic addition, HBr at room temperature.
Give the mechanism name, reagents and conditions for a reaction to turn an alkene into a dibromoalkane, and what is it the test for?
Electrophilic addition, Br2 at room temperature. This is the test for a double bond, brown to colourless.
Give the mechanism name, reagents and conditions for a reaction to turn a haloalkane into an alcohol.
Nucleophilic substitution, warm aqueous NaOH under reflux.
Give the mechanism name, reagents and conditions for two possible reactions to turn an alkene into an alcohol.
1) Hydration, phosphoric acid (H3PO4) catalyst, steam, 300°C, 60atm.
2) Hydration, water, sulphuric acid (H2SO4) catalyst.
Give the mechanism name, reagents and conditions for a reaction to turn an alcohol into an alkene.
Dehydration, conc. sulphuric acid (H2SO4), under reflux.
Give the mechanism name, reagents, colours and conditions for a reaction to turn a primary/secondary alcohol into an aldehyde/ketone.
Oxidisation, acidified K2Cr2O7, heat in distillation apparatus. This changes from orange to green.
Give the mechanism name, reagents and conditions for a reaction to turn an aldehyde/ketone into an alcohol.
Reduction, NaBH4 in water with methanol.
Give the mechanism name, reagents and conditions for a reaction to turn an aldehyde into a carboxylic acid.
Oxidisation, acidified K2Cr2O7, under reflux.
Give the mechanism name, reagents and conditions for a reaction to turn a aldehyde/ketone into a hydroxynitrile.
Nucleophilic addition, aqueous KCN or gaseous HCN with sulphuric acid at room temperature.
Give the mechanism name, reagents and conditions for a reaction to turn a carboxylic acid into an ester.
Esterification, alcohol, conc. sulphuric acid catalyst, heat.
Give the mechanism name, reagents and conditions for two reactions to turn an ester into a carboxylic acid.
1) Hydrolysis, water, dilute sulphuric acid catalyst, under reflux.
2) Hydrolysis, dilute aqueous NaOH under reflux.
Give the mechanism name, reagents and conditions for a reaction to turn an acyl chloride/acid anhydride into a N-substituted amine.
Nucleophilic addition elimination, amine, room temperature.
Give the mechanism name, reagents and conditions for a reaction to turn an acyl chloride/acid anhydride into a primary amine.
Nucleophilic addition elimination, ammonia, room temperature.
Give the mechanism name, reagents and conditions for a reaction to turn an acyl chloride/acid anhydride into an ester.
Nucleophilic addition elimination, alcohol, room temperature.
Give the mechanism name, reagents and conditions for a reaction to turn an acyl chloride/acid anhydride into a carboxylic acid.
Nucleophilic addition elimination, water, room temperature.
Give the reaction name, mechanism name, reagents and conditions for a reaction to turn benzene into a phenylketone.
Electrophilic substitution, acylation, acyl chloride, aluminium chloride catalyst, reflux, non-aqueous.
Give the reaction name, mechanism name, reagents and conditions for a reaction to turn benzene into nitrobenzene.
Electrophilic subtitution, nitration, conc. sulfuric acid, conc. nitric acid, below 55 degrees celcius.
Give the reaction name, reagents and conditions for two reactions to turn nitrobenzene into an aromatic amine.
Reduction, tin, conc. hydrochloric acid, reflux, sodium hydroxide.
OR H2 with a nickel catalyst.
Give the mechanism name and reagents for a reaction to turn an aromatic amine into N-phenylethanamide.
Nucleophilic addition elimination, ethanoyl chloride.
How can we distinguish between haloalkanes? Give each step of the method.
1) Produce an alcohol and the halide ions by reacting the haloalkane with sodium hydroxide.
2) Add nitric acid to remove any ions that may interfere with the test.
3) Add silver nitrate to produce a precipitate of a silver halide.
What colours are each of the silver halide precipitates?
F: no precipitate
Cl: white precipitate
Br: cream precipitate
I: yellow precipitate
If we cannot see the difference in colour between silver halide precipitates, what can we test their solubility with, and what will the results show for each of the silver halides?
Ammonia.
Cl: dissolves in dilute
Br: dissolves in concentrated
I: insoluble
How do we calculate percentage yield?
Actual yied over theoretical yield.
How do we calculate theoretical yield?
Work out the moles from the mass of a reactant, then calculate the theoretical mass of the product.
How do we calculate percentage atom economy?
Mass of desired product over the total mass of the reactants.
