# What results from the reaction of 5-bromopentan-1-ol and NaOH?

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.

An $\mathrm{S_N2}$:
Deprotonation followed by an intramolecular Williamson ether synthesis ($\mathrm{S_N2}$):
An $\mathrm{E2}$: