Is there an intramolecular hydrogen bonding in 2-hydroxybenzonitrile? If so, then the $\mathrm pK_\mathrm a$ order should be meta > ortho > para but the actual order is meta > para > ortho.

I think since the $\ce{-CN}$ group is linear in shape hence the distance between $\ce{-OH}$ group and $\ce{-CN}$ is large so there should not be any hydrogen bonding between them.

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  • 5
    $\begingroup$ You think right. $\endgroup$ Mar 29 at 9:32


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