kindly someone please explain the reason behind this behaviour despite the fact that oxygen is more electronegative and forms stronger hydrogen bond.

  • $\begingroup$ Possible duplicate of Solubility of n-butanol and n-butanamine (however, no answers yet) $\endgroup$ – user7951 May 12 '16 at 12:40
  • $\begingroup$ More soluble in what? Water? $\endgroup$ – aventurin May 12 '16 at 18:36
  • $\begingroup$ yes they are more soluble in water $\endgroup$ – aks0854 May 14 '16 at 21:53
  • $\begingroup$ @Loong ,yes this is what I am talking about. 1 comment in that question's discussion mentions about H-bonding but i think both amine( 2H +1 LP) and alcohol (1H+ 2LP) will be able to form 3 H-bonds. Correct me if I am wrong $\endgroup$ – aks0854 May 14 '16 at 21:59

I think it may be due to van der waals force (v.w.f). For both alcohols and amines the v.w.f acting between them and water molecules is keesom force i.e. dipole dipole interaction. In such case v.w.f is directly proportional to molecular mass , but if the molecular mass is also same then v.w.f is directly proportional to surface area of molecule which is inversely proportional to branching. Hence since amines have more branching than alcohol they have less surface area and hence less van der waals force. Due to weaker v.w.f amines are less soluble than alcohol. Please correct me if I am wrong.

  • $\begingroup$ Please someone comment on my answer. Am I right or wrong $\endgroup$ – Sameer nilkhan Dec 23 '19 at 9:52

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