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Question #44467
The Question
The electrophilic addition of \ce{Br2} to 4-\textit{tert}-butylcyclohexene in \ce{CCl4} at yields two possible \textit{trans}-dibromide stereoisomers: the diaxial product (A) and the diequatorial product (B). The thermodynamic parameters for the respective reaction pathways are given below:
\textbf{Pathway A (Diaxial):} , ,
\textbf{Pathway B (Diequatorial):} , ,
Determine the standard Gibbs free energy of reaction () for the formation of the major product at .
Options
- A.
-80.0 kJ/mol
- B.
-100.0 kJ/mol
- C.
41.0 kJ/mol
- D.
59.5 kJ/mol
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Numerical_Precision
Improve calculation stamina and avoid rounding errors in high-stakes competitive examinations.
Concepts Behind This Question
Stereochemical Outcome of Halogenation|Gibbs Energy and Spontaneity|State vs Path Functions
Why This Question Is Tricky
Common Mistakes
The question tests the student's ability to distinguish between kinetic and thermodynamic control in the context of stereochemical halogenation.
The 'hidden variable' is the irreversibility of bromination at room temperature, which dictates kinetic control.
Students often calculate the overall reaction spontaneity () and incorrectly assume that the most thermodynamically stable product (diequatorial, ) will be the major product.
However, the rigid conformation of 4-tert-butylcyclohexene forces the bromonium ion opening to proceed via a lower-energy chair-like transition state (Fuerst-Plattner rule), leading to the less stable diaxial product.
By calculating , students must identify the kinetically favored pathway and then report its corresponding .
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Hydrocarbons - Class 11 Part 2 |
| Concept | Stereochemical Outcome of Halogenation |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |