Leaving Group Ability
Alcohols are terrible leaving groups and need to be converted to different functional groups in order to improve. These groups are:
- Conversion to water through protonation.
- Conversion to a tosyl group through tosylation.
- Conversion to a mesyl group through mesylation.
- Conversion to an alkyl halide (R-X) with treatment with HX.
Example: Reactions to make -OH a better leaving group.
Example: Alcohol as a Leaving Group
Provide a reagent (or reagents) for the reaction shown below.
- a reagent like PBr3 will not work here as it reacts via an SN2 reaction and this is a tertiary alkyl halide
- the correct reagent here is HBr to react via an SN1 reaction