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.

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

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

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)

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

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

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

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

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

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