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Question #44508

Difficulty: 8/10 | 🟢 Free

The Question

In the Walsh and Coulson-Moffitt models of cyclopropane (\ceC3H6\ce{C3H6}) at 298 K298\text{ K}, carbon atoms rehybridize to minimize Baeyer strain. NMR data (J\ceC−H≈160 HzJ_{\ce{C-H}} \approx 160\text{ Hz}) indicates that the two \ceC−H\ce{C-H} bonds on each carbon are formed using exactly sp2sp^2 hybrid orbitals. The \ceC−C\ce{C-C} bonds are consequently formed by the 'bent' overlap of spnsp^n orbitals. Due to the spatial delocalization of these bent bonds (increasing positional uncertainty Δx\Delta x), 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 nn for the \ceC−C\ce{C-C} bonding orbitals, (2) the cosine of the inter-orbital angle (cos⁡θinter-orbital\cos \theta_{\text{inter-orbital}}) between the two \ceC−C\ce{C-C} bonds on the same carbon, and (3) the ratio of the lowest electronic excitation energy of cyclopropane to that of propane (ΔEcycloΔEpropane\frac{\Delta E_{\text{cyclo}}}{\Delta E_{\text{propane}}}).

Options

  • A.

    5,  −0.20,  <15,\; -0.20,\; < 1

  • B.

    4,  −0.25,  <14,\; -0.25,\; < 1

  • C.

    5,  −0.20,  >15,\; -0.20,\; > 1

  • D.

    3,  −0.33,  >13,\; -0.33,\; > 1

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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 sp3sp^3 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

SubjectChemistry
ChapterHydrocarbons - Class 11 Part 2
ConceptCycloalkane Ring Strain
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree