See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

# Identifying the Ambident Nucleophile **Definition:** An ambident nucleophile has two different nucleophilic sites and can attack an electrophile at either position, depending on reaction conditions. ## Analysis of Each Option: **(1) $NH_2OH$ (Hydroxylamine)** - Two nucleophilic sites: $N$ (nitrogen with lone pair) and $O$ (oxygen with lone pair) - Can attack at nitrogen: $R-N=OH$ (imine intermediate) - Can attack at oxygen: $R-O-NH_2$ (ether intermediate) - ✓ Ambident nucleophile **(2) $NCO^-$ (Isocyanate ion)** - Three atoms: $N-C≡O$ - Can attack through $N$ (soft nucleophile, kinetic product) - Can attack through $O$ (hard nucleophile, thermodynamic product) - ✓ Ambident nucleophile **(3) $NO_2^-$ (Nitrite ion)** - Two nucleophilic sites: $N$ and $O$ - Can attack through $N$ (giving R-NO₂, nitro compound) - Can attack through $O$ (giving R-ONO, alkyl nitrite) - ✓ Ambident nucleophile ## Conclusion: **Answer: (4) All of these** All three species possess two or more nucleophilic centers and can attack electrophilic carbons at different positions, making them ambident nucleophiles. The answer should be **(4)**, not (1).