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Question #44374

Difficulty: 8/10 | 🟢 Free

The Question

1-Methylcyclohex-1-ene is treated with $BD_3 \cdot THF$ followed by oxidation with $H_2O_2 / NaOH$ at $298\text{ K}$ . Which of the following accurately describes the major product formed?

Options

A.
Racemic mixture of $(1R, 2R)$ and $(1S, 2S)$ -2-deuterio-2-methylcyclohexan-1-ol
B.
Racemic mixture of $(1R, 2S)$ and $(1S, 2R)$ -2-deuterio-2-methylcyclohexan-1-ol
C.
Racemic mixture of $(1R, 2S)$ and $(1S, 2R)$ -2-deuterio-1-methylcyclohexan-1-ol
D.
Optically active $(1R, 2R)$ -2-deuterio-2-methylcyclohexan-1-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|Optical Activity and Enantiomers

Why This Question Is Tricky

Common Mistakes

This question tests the integration of regioselectivity (anti-Markovnikov), stereospecificity (syn-addition), and absolute configuration (R/S) in a cyclic system.

The 'Hidden Variable' is translating the relative syn-stereochemistry of D and OH into absolute IUPAC stereodescriptors.

Students often fall into the trap of assuming that because the -OH and -CH3 groups end up trans to each other, the reaction must have proceeded via anti-addition, leading them to incorrectly choose the (1R, 2S)/(1S, 2R) diastereomer.

Additionally, failing to recognize the prochiral nature of the starting alkene leads to the incorrect assumption of optical activity.

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