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Which hydrogens are the most acidic in a THF molecule? I understand the main factors that influence acidity, but I can't seem to figure this one out and I have not gotten any answers on the internet.

My friend and I were joking around about chemistry and something about deprotonating an ether came up. That question really caught my attention. I was split between two answers for deprotonating THF:

  1. One of the carbons bonded to the oxygen atom would be deprotonated due to a stronger inductive effect by the oxygen atom.

  2. One of the carbons further away from the oxygen atom because the oxygen has a partial negative charge and some lone pairs, so deprotonating a carbon bonded to the oxygen atom would cause some electrostatic repulsion and lone-pair repulsion.

Is any of this correct or is there another explanation?

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  • $\begingroup$ This is both pretty obvious and not really important, soo not a surprise you wouldn't find a ready answer. $\endgroup$
    – Mithoron
    Oct 16, 2023 at 19:57

1 Answer 1

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According to this paper

The principal pathway for decomposition of THF by alkyllithiums is deprotonation at C-2, α to oxygen, to give 2, followed by a reverse [3 ю 2] cycloaddition of the resulting anion to yield one molecule of ethylene plus one molecule of the lithium enolate of acetaldehyde

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