Resonance And Mesomeric Effect
While comparing contributing resonance structures of a conjugated species, which feature makes one canonical form contribute more to the resonance hybrid?
Select the correct option:
Solution
Greater number of covalent bonds with complete octets
Resonance describes a real molecule as a weighted blend of several canonical structures, and the rules for judging their relative importance follow from energetic stability. A canonical form contributes more when it has the maximum number of covalent bonds and when its atoms, especially second-period elements, satisfy the octet rule, because such a structure is lower in energy. Maximum separation of unlike charges is unfavourable since charge separation costs energy, so that option describes a minor contributor, not a major one. Placing negative charge on the least electronegative atom is destabilising; negative charge prefers the more electronegative atom, so that option is wrong. Having the fewest covalent bonds means more broken or dative interactions and higher energy, making it a poor contributor rather than a dominant one. Thus the form with more bonds and complete octets dominates the hybrid, in line with the NCERT guidelines on judging resonance contributors, which also state that a contributor should keep the same atomic positions and differ only in electron placement. Applying these rules lets a student rank canonical forms and predict where charge density actually accumulates in the real molecule, a skill tested repeatedly in JEE questions on stability and reactivity. Plausibility check: lower-energy, well-bonded, octet-complete structures resemble the true hybrid most closely, so they must contribute most, while highly charge-separated forms remain only minor contributors.
🔒 Solution Hidden from View
Submit your answer to unlock the detailed step-by-step solution.
About This Question
- Subject
- chemistry
- Chapter
- some basic principles of organic chemistry
- Topic
- resonance and mesomeric effect
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Greater number of covalent bonds with complete octets
Resonance describes a real molecule as a weighted blend of several canonical structures, and the rules for judging their relative importance follow from energetic stability. A canonical form contributes more when it has the maximum number of covalent bonds and when its atoms, especially second-period elements, satisfy the octet rule, because such a structure is lower in energy. Maximum separation of unlike charges is unfavourable since charge separation costs energy, so that option describes a minor contributor, not a major one. Placing negative charge on the least electronegative atom is destabilising; negative charge prefers the more electronegative atom, so that option is wrong. Having the fewest covalent bonds means more broken or dative interactions and higher energy, making it a poor contributor rather than a dominant one. Thus the form with more bonds and complete octets dominates the hybrid, in line with the NCERT guidelines on judging resonance contributors, which also state that a contributor should keep the same atomic positions and differ only in electron placement. Applying these rules lets a student rank canonical forms and predict where charge density actually accumulates in the real molecule, a skill tested repeatedly in JEE questions on stability and reactivity. Plausibility check: lower-energy, well-bonded, octet-complete structures resemble the true hybrid most closely, so they must contribute most, while highly charge-separated forms remain only minor contributors.
This medium difficulty chemistry question is from the chapter some basic principles of organic chemistry, covering the topic of resonance and mesomeric effect. It appeared in the 2025 exam.
Looking for more practice? Explore all chemistry questions or browse some basic principles of organic chemistry questions on RankGuru.