SN1 v SN2: Leaving group

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what are the two factors to consider with halides as leaving groups?
C-X bond strength and halide anion stability
Why do alcohols and ethers no react with nucleophiles?
pKa of leaving group is too high so not a good leaving group
how to turn alcohol into good leaving groups?
protonate with strong acid or transform OH into a sulfonate ester
What is used to convert an alcohol to a sulfonate ester?
Tosyl chloride, pyridine
Why is tosylate a good leaving group?
Negative charge delocalised on three oxygen atoms: stabilised
how are ethers as leaving groups?
poor (pka 16), need activation by a strong acid or lewis acid
Describe the properties of strained ethers:
strained (internal angle 60)
sp3 hydridised
very large deviation from ideal tetrahedral angle: angle strain
what happens to epoxides in acidic conditions?
protonated, react the same way as linear ethers
what type of reaction makes an epoxide?
sn2

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SN1 v SN2: Leaving group

Cards (9)

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