I want to ask a question about polar/non-polar (a)protic solvents.

The following information was given to me in the lecture hall today regarding solvents in organic chemistry.

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I recall the structure of Acetic Acid as $\ce{CH3COOH}$ but surely given the $\ce{O-H}$ dipole, wouldn't that make Acetic acid a Polar Protic solvent i.e. the $\ce{H}$ attached to the $\ce{O-H}$ can be involved in hydrogen bonding?

Am I incorrect in this instance? Shouldn't $\ce{CH3COOH}$ be classified as a polar protic solvent?

  • $\begingroup$ Probably a typo. $\endgroup$ – Michael Lautman May 30 '19 at 21:02
  • $\begingroup$ It's not a typo. CH3COOH has particularly low dielectric constant. While it doesn't disqualify it from category of "polar solvents", it should hamper solubility of salts. $\endgroup$ – Mithoron May 30 '19 at 21:58
  • 1
    $\begingroup$ @Mithoron that's true. Typically, the importance of polar/non-polar, protic/aprotic solvents is taught in the context of SN1/SN2 selectivity and is presented primarily in terms of dipole. Acetic acid has a dipole moment very similar to that of ethanol, and alcohols are commonly used to favour carbocation-forming reactions. That may be where the confusion is coming from. $\endgroup$ – Michael Lautman May 30 '19 at 23:07

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