• anonymous
Among tertiary, secondary and primary amines, rank them from least to most acidic
  • Stacey Warren - Expert
Hey! We 've verified this expert answer for you, click below to unlock the details :)
At vero eos et accusamus et iusto odio dignissimos ducimus qui blanditiis praesentium voluptatum deleniti atque corrupti quos dolores et quas molestias excepturi sint occaecati cupiditate non provident, similique sunt in culpa qui officia deserunt mollitia animi, id est laborum et dolorum fuga. Et harum quidem rerum facilis est et expedita distinctio. Nam libero tempore, cum soluta nobis est eligendi optio cumque nihil impedit quo minus id quod maxime placeat facere possimus, omnis voluptas assumenda est, omnis dolor repellendus. Itaque earum rerum hic tenetur a sapiente delectus, ut aut reiciendis voluptatibus maiores alias consequatur aut perferendis doloribus asperiores repellat.
  • katieb
I got my questions answered at in under 10 minutes. Go to now for free help!
  • taramgrant0543664
Hydrogen bonding plays a significant role in determining the physical properties of amines, although the hydrogen bonds in amines are not as strong as the hydrogen bonding that occurs in alcohols. Amines are intermediate in boiling point between similar alkanes and alcohols. Amines with fewer than six or seven carbons are water soluble. Of neutral organic molecules, amines are the strongest bases, although amines are still technically weak bases with basicity constant, Kb, between 10-3 to 10-5. Here is an interesting discussion of the comparison of the basicity of different types of amines: Ammonia is more basic than primary amines which are themselves more basic than tertiary amines which are in turn more basic than secondary amines. Notice the irregularity of this patter. This strange order of basicity occurs because of the combination of two effects, the stabilization of alkylammonium cation by the inductive release of negative charge by the alkyl substituents. The other effect, which tends in the opposite direction, is the ability of water to solvate and stabilize the cation through hydrogen bonding. While tertiary ammonium cations are more stabilized by induction, secondary ammonium cations are more stabilized by solvation.

Looking for something else?

Not the answer you are looking for? Search for more explanations.