Why can the reaction between a primary amine and a halogenoalkane lead to a mixture of products including tertiary amines and quaternary ammonium salts?

Multiple substitution is possible because the secondary and tertiary amines formed can also act as nucleophiles and react further.

How does a primary aliphatic amine act when it reacts with copper(II) ions in aqueous solution?

It acts as a ligand, donating its lone pair to the copper ion to form a complex ion.

Why are primary aliphatic amines stronger bases than ammonia?

Alkyl groups have a positive inductive effect, which increases electron density on the nitrogen and makes the lone pair more available for protonation.

Why are primary aromatic amines weaker bases than ammonia?

The nitrogen lone pair is delocalised into the benzene ring, making it less available for protonation.

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Organic Chemistry III

Reactions of amines and preparing them

3 things to know
Papers 2 and 3

Overview

Amines reacting with halogenoalkanes to give a mixture of products, amines as ligands with copper(II) ions, why aliphatic amines are stronger and aromatic amines weaker bases than ammonia, and preparing amines from halogenoalkanes, nitriles and aromatic nitro-compounds.

What you need to know

Answer each one before you reveal it.

Your recallNot started

Key term

Why is excess ammonia used when preparing a primary amine from a halogenoalkane?

Key term

What reagents are used to reduce an aromatic nitro-compound to an aromatic amine?

Key term

In the reaction between an amine and a halogenoalkane, which part of the halogenoalkane does the amine's lone pair attack?

Questions from this subtopic

Each one with the model answer underneath.

1
What type of reaction mechanism occurs when a primary amine reacts with a halogenoalkane?
Model answer
Nucleophilic substitution.
2
In the reaction between an amine and a halogenoalkane, which part of the halogenoalkane does the amine's lone pair attack?
Model answer
The carbon atom bonded to the halogen.
3
Why can the reaction between a primary amine and a halogenoalkane lead to a mixture of products including tertiary amines and quaternary ammonium salts?
Model answer
Multiple substitution is possible because the secondary and tertiary amines formed can also act as nucleophiles and react further.
4
How does a primary aliphatic amine act when it reacts with copper(II) ions in aqueous solution?
Model answer
It acts as a ligand, donating its lone pair to the copper ion to form a complex ion.
5
Why are primary aliphatic amines stronger bases than ammonia?
Model answer
Alkyl groups have a positive inductive effect, which increases electron density on the nitrogen and makes the lone pair more available for protonation.
6
Why are primary aromatic amines weaker bases than ammonia?
Model answer
The nitrogen lone pair is delocalised into the benzene ring, making it less available for protonation.

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Reactions of amines and preparing them

Overview

What you need to know

Why is excess ammonia used when preparing a primary amine from a halogenoalkane?

What reagents are used to reduce an aromatic nitro-compound to an aromatic amine?

In the reaction between an amine and a halogenoalkane, which part of the halogenoalkane does the amine's lone pair attack?

Questions from this subtopic

What type of reaction mechanism occurs when a primary amine reacts with a halogenoalkane?

In the reaction between an amine and a halogenoalkane, which part of the halogenoalkane does the amine's lone pair attack?

Why can the reaction between a primary amine and a halogenoalkane lead to a mixture of products including tertiary amines and quaternary ammonium salts?

How does a primary aliphatic amine act when it reacts with copper(II) ions in aqueous solution?

Why are primary aliphatic amines stronger bases than ammonia?

Why are primary aromatic amines weaker bases than ammonia?

Other ways to work this

What is inside Levo

The 3-step method, run for you

Cram a whole paper in one sitting

Blank Blitz makes facts automatic

Build It gets the exam shape right

Test It catches misconceptions

Brain Breaks between sessions

Every question in Organic Chemistry III, on a schedule.