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Question #44234
The Question
Consider the gas-phase heterolytic cleavage of 2-chloro-3-methylbutane () to form the thermodynamically most stable rearranged carbocation intermediate () and a chloride ion () at 298 K.
Given the following thermodynamic parameters: Standard enthalpy of formation of , Standard enthalpy of formation of , The theoretical standard enthalpy of formation of the localized (un-hyperconjugated) carbocation is . The hyperconjugative stabilization energy is per -C-H bond.
Calculate the actual enthalpy of reaction () for this heterolytic cleavage, accounting for the hyperconjugative stabilization of the final rearranged carbocation.
Options
- A.
694 \text{ kJ/mol}
- B.
742 \text{ kJ/mol}
- C.
790 \text{ kJ/mol}
- D.
886 \text{ kJ/mol}
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Mechanism_Trap
Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.
Concepts Behind This Question
Hess's Law Application|SN1 Carbocation Rearrangement|Hyperconjugation Logic
Why This Question Is Tricky
Common Mistakes
This problem tests the intersection of thermodynamic state functions (Hess's Law) and structural organic chemistry (carbocation rearrangement and hyperconjugation).
The 'Hidden Variable' is the enthalpy offset provided by hyperconjugation.
Students often calculate the of the reaction based on theoretical ground states, neglecting that the intermediate's energy is significantly modulated by orbital overlap ( delocalization).
Furthermore, the trap penalizes students who fail to perform the 1,2-hydride shift, as calculating the stabilization energy for the initial carbocation (4 -H) leads directly to distractor B.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Thermodynamics - Class 11 Part 1 |
| Concept | Hess's Law Application |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |