sulfonyl chloride very weak base ……why?

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Presentation transcript:

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

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 (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.