Wize University Organic Chemistry Textbook > Nucleophilic Substitutions and Elimination Reactions
Alcohol As a Leaving Group
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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.
Wize Concept
Remember you can return to the Important Terminology Lesson (7.1) for a reminder about good leaving groups!
Example: Reactions to make -OH a better leaving group.
Wize Tip
Pyridine is usually added as a base when a reaction produces HCl to neutralize the reaction!
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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