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Question #44457

Difficulty: 8/10 | 🟢 Free

The Question

The conformational landscapes of 1,2-difluoroethane (Molecule A) and NN-methylacetamide (Molecule B) exhibit significant deviations from simple steric models. Consider the following statements regarding their structural and thermodynamic properties at 298 K:

I. The global energy minimum of A corresponds to a F-C-C-F dihedral angle θ≈60∘\theta \approx 60^\circ, primarily stabilized by two antiperiplanar σC−H→σC−F∗\sigma_{C-H} \rightarrow \sigma^*_{C-F} hyperconjugative interactions. II. The global energy minimum of B corresponds to a C-C-N-C dihedral angle ω≈180∘\omega \approx 180^\circ, dictated by nN→πC=O∗n_N \rightarrow \pi^*_{C=O} delocalization and minimization of steric strain. III. In highly polar solvents, the anti conformer of A becomes the global energy minimum because its zero dipole moment minimizes unfavorable solvent interactions. IV. The activation energy for rotation around the C-N bond in B is approximately 85 kJ/mol85 \text{ kJ/mol}, which is significantly higher than the C-C rotational barrier in A.

Which of the following combinations of statements is correct?

Options

  • A.

    I, II, and IV

  • B.

    I and II only

  • C.

    II, III, and IV

  • D.

    I, III, and IV

Check Your Answer

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

Alkane Conformation Energy Barriers|Peptide Bond Planarity

Why This Question Is Tricky

Common Mistakes

This question tests the 'Gauche Effect', a critical exception to the standard steric model of alkane conformations.

Students often incorrectly assume that the anti conformer is always the most stable due to minimized steric and dipole-dipole repulsions.

The hidden variable is the stereoelectronic σC−H→σC−F∗\sigma_{C-H} \rightarrow \sigma^*_{C-F} hyperconjugation, which overrides steric factors in highly electronegative systems.

Furthermore, it tests thermodynamic solvent effects on conformer stability (polar solvents stabilize the more polar gauche conformer, contrary to the distractor) and contrasts the rotational barriers of single bonds versus resonance-stabilized peptide bonds.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterHydrocarbons - Class 11 Part 2
ConceptAlkane Conformation Energy Barriers
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree