Chapter 28 - Organic synthesis Flashcards
What is the nitrile functional group ?
-CN
What are the two ways that nitriles can be formed ?
- From haloalkanes
- From aldehydes or ketones
How are nitriles made from haloalkanes ?
- Reacting haloalkanes with sodium cyanide in ethanol
- The length of the carbon chain increases
What type of mechanism is the formation of nitriles from haloalkanes ?
Nucleophilic substitution reaction
How are nitriles made from haloalkanes ?
They react with HCN and lead to an increase in the number of carbon atoms in the molecule
What type of mechanism is the formation of nitriles from aldehydes and ketones ?
Nucleophilic addition reaction
Why is HCN not used in the reactions ?
- It is far too poisonous
- An increased reaction rate can be obtained in the presence of cyanide ions
What is used instead of HCN in reactions ?
- Sodium cyanide or potassium cyanide
- This improves safety and increases reaction rates
How can nitriles be reduced ?
Nitriles can be reduced to amines by reacting with hydrogen in the presence of a nickel catalyst
How can nitriles be hydrolysed ?
Nitriles undergo hydrolysis to farm carboxylic acids by heating with dilute aqueous acid
What is alkylation ?
It is a reaction that transfers an alkyl group from a haloalkane to a benzene ring
Does alkylation need a halogen carrier catalyst ?
Yes
What is acylation ?
When benzene reacts with an acyl chloride
Does acylation require a halogen carrier catalyst ?
Yes
What is formed as a result of an acylation reaction ?
A ketone
