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Question #44376

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following reaction sequence: $\ce{CH3-C(CH3)2-CH=CH2 \xrightarrow[(ii) NaBH4, OH^-]{(i) Hg(OAc)2, H2O/THF} P}$ $\ce{P \xrightarrow{POCl3, pyridine, 0^\circ C} Q (Major)}$ $\ce{Q \xrightarrow[(ii) Zn, H2O]{(i) O3, CH2Cl2, 195 K} R + S}$ Identify the major products R and S.

Options

A.
2,2-Dimethylpropanal and methanal
B.
Propanone (2 equivalents)
C.
3-Methylbutan-2-one and methanal
D.
2,2-Dimethylpropanoic acid and methanoic acid

Check Your Answer

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

Oxymercuration-Demercuration Specificity|Acid-Catalyzed Hydration Mechanism

Why This Question Is Tricky

Common Mistakes

This blueprint tests the student's ability to differentiate between the regioselectivity and the actual mechanism of hydration reactions.

While both acid-catalyzed hydration and oxymercuration-demercuration follow Markovnikov's rule, the hidden variable is the transition state geometry.

The bridged mercurinium ion in oxymercuration blocks the 1,2-alkyl shift.

The distractors mathematically map to the products formed if the student falls for the carbocation rearrangement trap and subsequently applies either Zaitsev's or Hofmann's rule during elimination.

Quick Facts About This Question

Question Information

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