Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct order of stability among the following canonical structures:
Options
- A(ii) > (i) > (iii)
- B(i) > (iii) > (ii)
- C(i) > (ii) > (iii)
- D(iii) > (i) > (ii)
Correct answer
B. (i) > (iii) > (ii)
Step-by-step solution
The stability of canonical structures with the same number of covalent bonds and complete octets is determined by the electronegativity of the atom bearing the negative charge. In structure (i), the negative charge is present on the highly electronegative oxygen atom ( O^- ). In structure (ii), the negative charge is present on the least electronegative carbon atom ( C^- ). In structure (iii), the negative charge is present on the moderately electronegative nitrogen atom ( N^- ). A negative charge is more stable wh