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Question #45077
The Question
Consider the solvolysis of 2-bromo-3-ethyl-3-methylpentane in boiling water (\ce{H2O}, ). The reaction proceeds via an mechanism to yield a major rearranged product . What is the correct IUPAC name of ?
Options
- A.
3,4-dimethylhexan-3-ol
- B.
3-ethyl-2-methylpentan-3-ol
- C.
4-ethyl-3-methylpentan-3-ol
- D.
3-ethyl-3-methylpentan-2-ol
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
IUPAC Nomenclature Priority|SN1 Carbocation Rearrangement|Solvent Effects on Reactivity
Why This Question Is Tricky
Common Mistakes
This problem tests two lethal traps.
First, students must correctly identify that an ethyl shift is thermodynamically favored over a methyl shift due to the hyperconjugative stability of the resulting carbocation (6 -H vs 5 -H).
Second, the 'Hidden Variable' is the re-evaluation of the IUPAC principal chain.
Students often anchor their naming to the original 5-carbon parent chain of the substrate, incorrectly naming the rearranged product as a pentane derivative (4-ethyl-3-methylpentan-3-ol).
The rearrangement fundamentally alters the longest continuous carbon chain, forcing a shift from a pentane to a hexane derivative.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Organic Chemistry – Some Basic Principles and Techniques - Class 11 Part 2 |
| Concept | IUPAC Nomenclature Priority |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |