Transcript CH 11-3 Power Point

CH 11-3: Substitution Reactions of Alcohols:
Leaving group activation as a Sulfonate Ester
sulfonyl chloride
"sulfonate ester"
excellent leaving group
very weak base
……why?
•The sulfonate leaving group is stabilized by resonance
Substitution Reactions of Alcohols:
Sulfonate Ester Activation
•A common sulfonate leaving group is the “Tosyl” group:
Synthesis of Ethers: R-O-R’
(1) Alcohol is an SN2 Nucleophile
General Reaction:
•Why not 2o or 3o alkyl halide?
(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.