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Question #44371

Difficulty: 8/10 | 🟢 Free

The Question

An unknown alkene $X$ ( $C_6H_{12}$ ) undergoes reductive ozonolysis to yield formaldehyde and 2,2-dimethylpropanal. When $X$ is subjected to acid-catalyzed hydration using dilute $H_2SO_4$ at 298 K, it forms compound $P$ as the major product. Conversely, when $X$ is treated with $BH_3 \cdot THF$ followed by oxidation with alkaline $H_2O_2$ , it yields compound $Q$ as the major product. Identify the correct IUPAC names for $P$ and $Q$ .

Options

A.
P: 2,3-dimethylbutan-2-ol ; Q: 3,3-dimethylbutan-1-ol
B.
P: 3,3-dimethylbutan-2-ol ; Q: 3,3-dimethylbutan-1-ol
C.
P: 2,3-dimethylbutan-2-ol ; Q: 2,3-dimethylbutan-1-ol
D.
P: 3,3-dimethylbutan-2-ol ; Q: 3,3-dimethylbutan-2-ol

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Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Mechanism_Trap

Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.

Concepts Behind This Question

Hydroboration-Oxidation Regiochemistry|Acid-Catalyzed Hydration Mechanism|SN1 Carbocation Rearrangement

Why This Question Is Tricky

Common Mistakes

Tests the critical mechanistic divergence between Acid-Catalyzed Hydration (ACH) and Hydroboration-Oxidation (HBO).

Students often apply Markovnikov's rule blindly, failing to recognize that ACH proceeds via a carbocation intermediate prone to a 1,2-alkyl shift (skeletal rearrangement) to maximize stability.

Conversely, HBO is a concerted process with a four-membered transition state that strictly prevents carbocation formation and rearrangement, resulting in a pure anti-Markovnikov, non-rearranged product.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Alcohols, Phenols, and Ethers - Class 12
Concept	Hydroboration-Oxidation Regiochemistry
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free