1. CH 11-3: Substitution Reactions of Alcohols: Leaving group activation as a Sulfonate Ester
sulfonyl chloride
very weak base ……why?
The sulfonate leaving group is stabilized by resonance

2. Substitution Reactions of Alcohols: Sulfonate Ester Activation
A common sulfonate leaving group is the “Tosyl” group:

3. Synthesis of Ethers: R-O-R’ (1) Alcohol is an SN2 Nucleophile
General Reaction:
Why not 2o or 3o alkyl halide?

4. (2) Ether Synthesis by SN1 Substitution
(2) Ether Synthesis by SN1 Substitution. Write a complete mechanism for the balanced equation shown below. Your mechanism must consist of a series of numbered, balanced equations for each chemical step, and curved arrows to show the movement of electron pairs.