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Question #44508
The Question
In the Walsh and Coulson-Moffitt models of cyclopropane () at , carbon atoms rehybridize to minimize Baeyer strain. NMR data () indicates that the two bonds on each carbon are formed using exactly hybrid orbitals. The bonds are consequently formed by the 'bent' overlap of orbitals. Due to the spatial delocalization of these bent bonds (increasing positional uncertainty ), the Heisenberg Uncertainty Principle dictates a lower confinement energy for the bonding electrons, which raises the HOMO energy. Identify the correct tuple for: (1) the hybridization index for the bonding orbitals, (2) the cosine of the inter-orbital angle () between the two bonds on the same carbon, and (3) the ratio of the lowest electronic excitation energy of cyclopropane to that of propane ().
Options
- A.
- B.
- C.
- D.
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Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Exception_Exposure
Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.
Concepts Behind This Question
Cycloalkane Ring Strain|Alkane Conformation Energy Barriers|Heisenberg Uncertainty Principle
Why This Question Is Tricky
Common Mistakes
The question tests the 'Chemical Exception' of cyclopropane's bonding, where classical Baeyer strain (assuming rigid orbitals) fails to explain its chemical properties.
Students often overlook that highly strained rings rehybridize (Bent's Rule/Walsh orbitals) to place more p-character in the strained bonds, creating 'bent bonds'.
The hidden variable is the application of the Heisenberg Uncertainty Principle: the spatial delocalization of these bent bonds reduces electron confinement, raising the HOMO energy and causing cyclopropane to exhibit alkene-like electronic excitations (absorbing at longer wavelengths/lower energy than normal alkanes).
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Hydrocarbons - Class 11 Part 2 |
| Concept | Cycloalkane Ring Strain |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |