If you reacted TsOH with a secondary or tertiary alcohol, will you ever see a racemic mixture of OTs substituted products after the water group leaves? Is OTs just too weak of a nucleophile to ever substitute?

  • $\begingroup$ It is really a very poor nucleophile $\endgroup$ – Waylander Mar 24 at 9:46
  • $\begingroup$ You are reacting a very weak base with very weak acid like a tertiary alcohol, so no. $\endgroup$ – Aditya Roychowdhury Mar 24 at 11:04

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