1 Answer | Add Yours
The amide anion (NH2-) is much, much more basic than the chloride anion (Cl-). This is because of their conjugate acids. Strong acids have weak conjugate bases and weak acids have stronger conjugate bases. The conjugate acid of Cl- is HCl, a very strong acid called hydrochloric acid. Since HCl is a strong acid and ionizes completely in water, Cl- is a very weak base. The conjugate acid of NH2- is NH3, called ammonia. Ammonia is actually itself a weak base, so its conjugate base NH2- is an incredibly strong base so it can get an extra proton to regenerate NH3 which is much more stable.
As a result of the relative basicity of NH2- and Cl-, we can determine that acid chlorides are much more reactive than amides. Acid chlorides will react with any number of nucleophiles to undergo displacement and lose a Cl- group. Amides, however, are very stable and will not react even under harsh conditions with nucleophiles to produce amide anions (NH2-).
So summarize, NH2- is a much stronger base than Cl-, and acid chlorides are much more reactive than amides.
We’ve answered 319,419 questions. We can answer yours, too.Ask a question