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Question #44457
The Question
The conformational landscapes of 1,2-difluoroethane (Molecule A) and -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 , primarily stabilized by two antiperiplanar hyperconjugative interactions. II. The global energy minimum of B corresponds to a C-C-N-C dihedral angle , dictated by 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 , 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 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
| Subject | Chemistry |
| Chapter | Hydrocarbons - Class 11 Part 2 |
| Concept | Alkane Conformation Energy Barriers |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |