Tosylation of an alcohol produces a what kind of leaving group?

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Multiple Choice

Tosylation of an alcohol produces a what kind of leaving group?

Tosylation turns an alcohol into a tosylate ester (R–O–Ts). The leaving group in this setup is the tosylate ion (p-toluenesulfonate, TsO−), which leaves readily in subsequent reactions. The sulfonate group is highly stabilized by resonance with the sulfonyl oxygens and the aromatic ring, making TsO− an excellent leaving group compared to hydroxide. This activation is why alcohols can undergo SN1/SN2 by first being converted to tosylates. The other options don’t fit because tosylation specifically creates a tosylate leaving group, not hydroxide, chloride, or phosphate.

Tosylation turns an alcohol into a tosylate ester (R–O–Ts). The leaving group in this setup is the tosylate ion (p-toluenesulfonate, TsO−), which leaves readily in subsequent reactions. The sulfonate group is highly stabilized by resonance with the sulfonyl oxygens and the aromatic ring, making TsO− an excellent leaving group compared to hydroxide. This activation is why alcohols can undergo SN1/SN2 by first being converted to tosylates. The other options don’t fit because tosylation specifically creates a tosylate leaving group, not hydroxide, chloride, or phosphate.

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