1. In the nucleophilic substitution reaction of haloalkanes with ammonia, instead of sharing it's lone pair with the carbocation, ammonia loses one of it's hydrogen and forms a primary amine, and the lone pair remains on the nitrogen. I can't understand why it is so. Why can't the nitrogen bond with carbon, it'll still have a fully filled octet.

  2. I have an unrelated query too - in the formation of nitroalkane by nucleophilic substitution of haloalkane and the reagent being silver nitrite. My sources point out that the silver atom is bonded to the oxygen atom attached to nitrogen by a single bond. I know that since the bond is covalent it wouldn't readily break at first in the reaction (correct me if I'm wrong), this leads to nitrogen sharing it's lone pair. Why doesn't oxygen share its lone pair?

  3. I think my thought process is wrong about haloalkane reactions. I believe that when the carbon halogen bond breaks carbon will only have 6 electrons in its valence shell, so there's no problem with it accepting a lone pair. But what about groups like $\ce{OH-}$ they give one electron alone to carbon when carbon needs two. I'm so confused could somebody please explain?

  • $\begingroup$ You mean to say that the reaction should be like this instead: $\ce{RX + NH3 -> (RNH3)+X-}$? i.e. an ionic salt of the cation $\ce{(RNH3)+}$ and the anion $\ce{X-}$. $\endgroup$ – Gaurang Tandon Mar 3 '18 at 14:37
  • $\begingroup$ yes, but the plus sign musnt be the charge on RNH3 but in between..I am wrong and I can't think why $\endgroup$ – Jacob P.J Mar 3 '18 at 14:38