The IR spectrum is shown here:

enter image description here

My assignments so far:

  • The 1728 and 1708 stretches correspond to $\ce{C=O}$ stretches in the keto form - the symmetric/asymmetric stretches respectively.

  • The 3003 stretches are typical $\ce{C-H}$ stretches.

  • The 1606 stretch corresponds to the $\ce{C=C}$ in the enol form. However, hidden under this peak there is also the $\ce{C=O}$ stretch in the enol form, which is lowered by conjugation to the $\ce{C=C}$ and the $\ce{O}$ of the $\ce{-OH}$ respectively.

I have two questions about the spectrum, however:

  1. Why is there no $\ce{-OH}$ peak? Even if the enol is hydrogen bonded to itself, there should still be an $\ce{-OH}$ peak in the $\pu{3400 cm^{-1}}$ range?

  2. Does the fact that the carbonyl peak in the enol form is hydrogen bonded change its shift? Assuming the only contribution to the lowering of the $\ce{C=O}$ stretching frequency is conjugation to the one $\ce{C=C}$ bond, this would lower the peak to ~$\pu{1655 cm^{-1}}$: Surely this would be seen as a peak in its own right? It seems to be shifted even lower to be fully hidden by the 1606 peak.

  • 1
    $\begingroup$ You're looking for the OH stretch, but what does that look like in this molecule? Because of internal hydrogen bonding, you might expect the bond strength to be very different, so the stretch frequency is not going to be where you would expect... $\endgroup$
    – Zhe
    Jan 28, 2018 at 17:36

1 Answer 1


OH str for beta diketones is tabulated from 3200 to 2400 1/cm. The shift is explained by resonance of the hydrogen bonded structure.

Its absorption features is small or unseen as for

  • commonly the ketonic form is highly dominant; i.e. we won't expect to see OH str in the acetaldehyde spectrum, even

  • owing to the above mentioned resonance, the dipole change associated to symmetric OH str is null, and it is minimal for the AS one.

The symmetry of 2,4-pentanedione makes the last point even more important.

Concerning the second part. The fact that the O of the carbonyl of the enoform is H bonded does further shift down the related CO str. Moreover, in addition to resonance with the C=C, note that again there will be resonance with the CO in beta as above, and this further shift the frequency to lower wn.


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