In our chemistry class, we noted three molecules that result from the reaction:

  1. pentane-(1,5)-diol


This one is simple to understand, simply a nucleophilic substitution between $\ce{Br^-}$ and $\ce{OH^-}$.

  1. (1,5)-epoxypentane


This is the main result, resulting from the intramolecular esterification of the two $\ce{OH^-}$ groups of the previous molecule. This is wrong, please see the explanation by ringo

  1. 4-penten-1-ol


This one, I don't understand. How is this a possible result? Could anyone help me understand? Thank you for your time.


1 Answer 1


The three reactions are:

An $\mathrm{S_N2}$:

Deprotonation followed by an intramolecular Williamson ether synthesis ($\mathrm{S_N2}$):

An $\mathrm{E2}$:

  • $\begingroup$ Thank you for the illustration, that made it much easier to understand. Would you mind me asking what software do you use to draw the equations? $\endgroup$
    – Glycerius
    Feb 15, 2017 at 20:45
  • 1
    $\begingroup$ ChemDraw. If you're at a university, they likely have a subscription and can get you a copy for free. $\endgroup$
    – ringo
    Feb 15, 2017 at 20:49

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