Q.Explain, in terms of the ionic vs. covalent character of the two reagents, why reacts with a haloalkane through carbon (giving an alkyl cyanide) while reacts through nitrogen (giving an alkyl isocyanide).
You're viewing a preview — the full solution, concept, methods & PYQ mapping are locked.
Start your 14-day free trial to unlock the full solution →Cyanide is an ambident nucleophile whose negative charge is shared between carbon and nitrogen, and which end reacts is decided by the character of the counter-cation. Potassium, a hard, weakly polarising cation, leaves essentially free and ionic in solution, so the reaction proceeds through the softer, more polarisable, more nucleophilic carbon end -- giving the cyanide (nitrile) product. Silver, by contrast, is a soft, strongly polarising cation that binds covalently and preferentially to cyanide's carbon end (silver-carbon bonds of this kind are well known to be strong and covalent), which effectively removes carbon fro …
Unlock everything free for 14 days
- Full step-by-step solutions
- Concept-first explanations
- Methods, shortcuts & mistakes
- PYQ mapping + timed mock tests
Full access for 14 days. No credit card required.