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Question #44496
The Question
An alkene () on reductive ozonolysis yields methanal and 2,2-dimethylpropanal. is subjected to three distinct hydration protocols at 298 K:
I. Catalytic hydration with dilute yields as the major product. II. Hydroboration-oxidation ( in THF, followed by /) yields as the major product. III. Oxymercuration-demercuration (/, followed by /) yields as the major product.
Identify the IUPAC names of , , and respectively.
Options
- A.
2,3-dimethylbutan-2-ol, 3,3-dimethylbutan-1-ol, 3,3-dimethylbutan-2-ol
- B.
3,3-dimethylbutan-2-ol, 3,3-dimethylbutan-1-ol, 2,3-dimethylbutan-2-ol
- C.
2,3-dimethylbutan-2-ol, 3,3-dimethylbutan-2-ol, 3,3-dimethylbutan-1-ol
- D.
3,3-dimethylbutan-1-ol, 2,3-dimethylbutan-2-ol, 3,3-dimethylbutan-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
Hydroboration-Oxidation Logic|Alkene Addition Regioselectivity
Why This Question Is Tricky
Common Mistakes
The 'Hidden Variable' being tested is the susceptibility of the substrate to carbocation rearrangement and how different hydration mechanisms handle it.
Students often erroneously apply the 1,2-methyl shift (valid only for the acid-catalyzed hydration) to hydroboration-oxidation or oxymercuration-demercuration, failing to recognize that the latter two bypass free carbocation intermediates, thus operating under strict kinetic and regiochemical control without rearrangement.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Hydrocarbons - Class 11 Part 2 |
| Concept | Hydroboration-Oxidation Logic |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |