Before You Begin
Question #44613
The Question
Consider the solvolysis of 2-bromo-3,3-dimethylbutane in at . Identify the major organic product formed.
Options
- A.
2,3-dimethyl-2-butene
- B.
2,3-dimethylbutan-2-ol
- C.
3,3-dimethylbutan-2-ol
- D.
3,3-dimethyl-1-butene
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
SN1 Carbocation Rearrangement|E1/E2 Solvent and Base Effects
Why This Question Is Tricky
Common Mistakes
Students typically memorize the heuristic that 'polar protic solvents favor SN1 over E1 during neutral solvolysis.' The trap lies in ignoring the hidden variables: elevated temperature and steric hindrance.
The rearranged tertiary carbocation is sterically congested, which raises the activation energy for nucleophilic attack.
Concurrently, the elevated temperature amplifies the entropic advantage of elimination, and the resulting alkene is exceptionally stable (tetrasubstituted).
This causes a mechanistic crossover where the E1 pathway dominates, violating the basic SN1 assumption.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Haloalkanes and Haloarenes - Class 12 |
| Concept | SN1 Carbocation Rearrangement |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |