Nucleophilic substitution of haloalkanes (hydrolysis)

What is a nucleophile

An electron pair donor

What are common nucleophiles that react with haloalkanes

• Hydroxide ions

• Water molecules

• Ammonia molecules

What happens when the nucleophile reacts with a haloalkane

The nucleophile replaces the halogen in a substitution reaction

Draw the mechanism of nucleophilic substitution

Products are a new alcohol and a halide ion as it keeps electrons

What does the rate of hydrolysis of a haloalkane depend on

The strength of the carbon-halogen bond in the haloalkane, the bond enthalpy

What is the order of the bond enthalpy of carbon-halogen bonds

1. C-F

2. C-Cl

3. C-Br

4. C-I

Why does C-I have the lowest bond enthalpy

Iodine has a larger atomic radius and more electron shielding, so the electrostatic attraction between the nucleus and the bonding electrons is weaker, giving a lower C–I bond enthalpy.

Draw a diagram of how you would carry out hydrolysis of a haloalkane