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Question #44496

Difficulty: 8/10 | 🟢 Free

The Question

An alkene XX (\ceC6H12\ce{C6H12}) on reductive ozonolysis yields methanal and 2,2-dimethylpropanal. XX is subjected to three distinct hydration protocols at 298 K:

I. Catalytic hydration with dilute \ceH2SO4\ce{H2SO4} yields PP as the major product. II. Hydroboration-oxidation (\ceB2H6\ce{B2H6} in THF, followed by \ceH2O2\ce{H2O2}/\ceNaOH\ce{NaOH}) yields QQ as the major product. III. Oxymercuration-demercuration (\ceHg(OAc)2\ce{Hg(OAc)2}/\ceH2O\ce{H2O}, followed by \ceNaBH4\ce{NaBH4}/\ceNaOH\ce{NaOH}) yields RR as the major product.

Identify the IUPAC names of PP, QQ, and RR 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

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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

SubjectChemistry
ChapterHydrocarbons - Class 11 Part 2
ConceptHydroboration-Oxidation Logic
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree