1. Reactions of haloalkanes…
Haloalkanes react by nucleophilic substitution.
A nucleophile is a species with either a negative charge or a δ- charge.
Haloalkanes possess a δ+ dipole as the C-X bond is polar.

2. Reactions of haloalkanes…
Always show the lone pair (if there is one) and draw the arrow going from there rather than the negative charge.

3. Reactions of haloalkanes…
Haloalkanes can be hydrolysed to form alcohols
Nucleophile: OH-
Reactant: Ethanol
Conditions: 50oC
The bond breaking is heterolytic

4. Reactions of haloalkanes…
The rate of hydrolysis is dependent on the C-X bond strength (which we’ve already covered).
Which chemical is used to allow us to measure this?
AgNO3(aq)

5. Reactions of alcohols…
Alcohols can be converted back into haloalkanes but the mechanism is not just the reverse of the hydrolysis.
An INTERMEDIATE species is formed

6. Reactions of alcohols…
Nucleophile: Br-
Reagent: NaBr
Conditions: Heat
H2SO4 catalyst

7. Reactions of alcohols…
Alcohols can be dehydrated to form alkenes through a loss of water.
One carbon loses an OH-
One carbon loses a H+
Reagents: Alcohol
Conditions: H2SO4 catalyst
170oC
Bond breaking is heterolytic
H2O

8. Reactions of alcohols…
When reacted with carboxylic acids, alcohols will form esters via a condensation reaction. O
R O C R’
Ester Bond
From acid
From alcohol

9. Reactions of alcohols…
The reaction between alcohol and carboxylic acid is in dynamic equilibrium
CH3CH2CH2OH + CH3COOH
CH3CH2CH2-O-C-CH3 + H2O
Propyl Ethanoate O

10. Reactions of alcohols…
Condensation
Reagents: alcohol & carboxylic acid
Catalyst: H2SO4
Conditions: heat
Hydrolysis
Reagents: ester & water
Catalyst: H2SO4 (or NaOH – A2 stuffs)
Conditions: reflux