Organic synthesis reactions

Question 1

Give the type of reaction, reagent and conditions for converting a halogenoalkane to an amine

Answer 1

nucleophilic substitution
halogenoalkane and excess ammonia
sealed container, ethanol as solvent

Question 2

Give the type of reaction, reagent and conditions for converting a halogenoalkane to a nitrile

Answer 2

nucleophilic substitution
halogenoalkane and potassium cyanide
ethanol as solvent, heat under reflux

Question 3

Give the type of reaction, reagent and conditions for converting an alcohol to a halogenoalkane

Answer 3

nucleophilic substitution

chlorination: primary or secondary alcohol and phosphorus pentachloride (PCl5)
chlorination: tertiary alcohol and conc HCl
bromination: alcohol, conc H2SO4 and KBr warmed
iodination: alcohol, red phosphorus and iodine heat under reflux

Question 4

Give the type of reaction, reagent and conditions for converting a halogenoalkane to an alcohol

Answer 4

nucleophilic substitution
halogenoalkane and potassium hydroxide
heat under reflux

Question 5

Give the type of reaction, reagent and conditions for converting an alcohol to an aldehyde

Answer 5

partial oxidation (of primary alcohol)
primary alcohol, potassium dichromate and dilute H2SO4
heat and distil off aldehyde (distillation with addition)

Question 6

Give the type of reaction, reagent and conditions for converting an aldehyde to an alcohol

Answer 6

nucleophilic addition/reduction
aldehyde and lithium tetrahydridoaluminate
dry ether and warm

Question 7

Give the type of reaction, reagent and conditions for converting an aldehyde to a carboxylic acid

Answer 7

oxidation
aldehyde, potassium dichromate and dilute H2SO4
heat under reflux

Question 8

Give the type of reaction, reagent and conditions for converting a carboxylic acid to a salt

Answer 8

neutralisation/acid-base
carboxylic acid and aqueous sodium hydroxide
room temperature

Question 9

Give the type of reaction, reagent and conditions for converting a salt to a carboxylic acid

Answer 9

acid-base
carboxylate salt and aqueous acid e.g. HCl
room temperature

Question 10

Give the type of reaction, reagent and conditions for converting a nitrile to an amine

Answer 10

2 ways:

1) reduction, lithium tetrahydridoaluminate and nitrile in dry ether
2) reduction, hydrogen gas with solid nickel catalyst, heated