6.4 Organic Synthesis Flashcards
How can nitriles be formed from haloalkanes ?
Reacting haloalkanes with NaCN or KCN in ethanol. This increased the length of the carbon chain. Occurs during nucleophilic substitution.
How are nitriles formed from aldehydes and ketones?
They react with HCN during nucleophilic addition. NaCN and sulphuric acid is used.
How are nitriles reduced ?
They can be reduced ti Maines by reacting hydrogen with a nickel catalyst.
How are nitriles hydrolysed ?
Undergo hydrolysis to form carboxylic acids by heating with dilute acid, such as HCl (aq).
What is alkylation ?
Reaction that transfers an alkyl group from a haloalkane to a benzene ring. Takes place in the presence of AlCl3.
What is acylation ?
When benzene reacts with an acyl chloride in the presence of AlCl3 catalyst, forming a ketone.
Alkene to haloalkane ?
Hydrogen halide
Alkene to alcohol ?
Hydration of steam and phosphoric acid catalyst.
Alcohol to alkene ?
Dehydration with sulfuric acid.
Alcohol to ester ?
Carboxylic acid and sulfuric acid under esterification.
Alcohol to haloalkane ?
NaX and sulphuric acid.
Haloalkane to primary alcohol ?
NaOH.
Alcohol to aldehyde ?
Acidified potassium dichromate and sulphuric acid under distillation.
Aldehyde to primary alcohol ?
NaBH4 and water under reduction.
Haloalkane to amine ?
NH3 and ethanol.
Haloalkane to nitrile ?
NaCN
Nitrile to amine ?
Hydrogen and Nickel catalyst during reduction.
Aldehyde to hydroxynitrile ?
NaCN acidified under nucleophilic addition.
Aldehyde/ alcohol to carboxylic acid ?
Acidified potassium dichromate under reflux.
Nitrile to carboxylic acid ?
Water and HCl under hydrolysis.
Carboxylic acid to ester ?
Esterification with an alcohol and sulphuric acid.
Ester to carboxylic acid ?
Dilute acid hydrolysis.
Carboxylic acid to acyl chloride ?
SOCl2
Acyl chloride to carboxylic acid ?
Water.
Ester to sodium salt ?
NaOH and alkaline hydrolysis.
Acyl chloride to primary amide ?
NH3
Acyl chloride to secondary amine ?
Primary amine.
Acyl chloride to ester ?
Add an alcohol.
