Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cbee on December 03, 2004, 08:10:33 PM
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Why are tosylates, triflates, etc. all more reactive in their corresponding Sn2 reaction in aprotic media (read: THF or Ether) than the iodides? HI is a stronger acid than tosic acid and therefore I- is a weaker base than TsO-, but the tosylate is about an order of magnitude better leaving group than I-. Why?
Cisco