AC13: Organic nitrogen compounds
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What is amine derived from
Ammonia molecules
What is a primary amine
Attached to only 1 carbon
Why do amine act as a base
Amines have a lone pair of electrons on the nitrogen
What a proton binds to an amine, what type of bond is formed
Dative covalent (coordinate) bond
What determines the electron density of the nitrogen in amines
The type of group attached to the nitrogen
What determines the strength of amine acting as a base
The availability of the lone pair of electrons on nitrogen
What is needed to make an aliphatic amine
• Halogenalkane • Excess ammonia
When reacting 1-chloroethane with excess ammonia, what is the products
Primary amine and ammonia chloride
How many molecules of ammonia are needed to react with halogenalkane
2
Why can secondary, tertiary and quaternary amines be formed from a primary amine
Primary amines still have a lone pair of electrons on the nitrogen so also acts as a nucleophile
How are aromatic amines made
Reducing nitro compounds such as nitrobenzene
When reducing nitro compounds, like nitrobenzene, what is the first step
Heat under nitrobenzene under reflux with concentrated hydrochloric acid and tin
When reducing nitrobenzene, how many [H] do you need
6, 2 for the nitro part attached to the ring and then 4 to form 2 molecules of water
What are amides derivatives of
Carboxylic acids
What is the difference between a carboxylic acid and an amide
The -OH in the carboxylic acid is substituted with a -NH2
What is the difference between amine and amides
Amides have a carbonyl functional group attached to -NH2 group
What are the conditions to make a primary amine
• Excess ammonia in ethanol
What mechanism type happens when excess ammonia reacts with a haloalkane
Nucleophilic substitution
When reacting haloalkane with ammonia, what would happen if the haloalkane is in excess
Further reactions can take place, forming secondary and tertiary amines
Why must the ammonia be in excess when reacting with a haloalkane
As the primary amine that is produced has a lone pair so can act as a nucleophile and form secondary and teritary amines, so excess ammonia is needed
What 2 reactants are needed to form a secondary amine
• Haloalkane • Excess ethanolic primary amine
What is the reducing agent when reducing nitrobenzene to phenylamine
• Tin / Sn • Concentrated HCl • Heated under reflux
What is the product of reducing nitrobenzene using tin and concentrated HCl
A salt since the conditions are acidic
What is reacted with the salt that is formed from the reduction of nitrobenzene with tin and concentrated HCl
Salt + OH- -> nitrobenzene + water