Chemistry - Counting number of acidic-H in a molecule

An aldehyde or a ketone with an alpha hydrogen forms a carbanion that resonates to enolate form. This leads to two canonical structures that are in resonance. The example below is a polyphenol compound extracted from turmeric, called curcumin.

enter image description here

source: Biomaterials. 2010 May;31(14):4179-85. doi: 10.1016/j.biomaterials.2010.01.142. Epub 2010 Feb 23. (

The hydrogens between two keto groups are most acidic. This is due to formation of two equivalent enol structures stabilized by hydrogen bonding. The structural requirement would be planarity of atoms involved in hydrogen bonding.

Below are 3-D structures of the given compound in the question above.

  • Structure without hydrogens

Bridgehead carbon is 4. Keto groups are at 2 , 5 and 8 (shaded in grey). Keto groups on 5 and 8 are not in the same plane . Hence Hydrogen on 4 , 22 (see figure with hydrogens) does not form stable hydrogen bonded enol structures as discussed in the above example.

Therefore, hydrogen at 8th one (pointing with red arrow) may not be acidic.

Note: 3-D structures have been drawn on Chem3Dpro

enter image description here

  • Structure with hydrogens

enter image description here

  • Structure with hydrogens (2nd view)

enter image description here