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Question #44471
The Question
Consider the following reaction sequence starting from 1-methylcyclohex-1-ene (\textbf{A}):
\textbf{A} \textbf{B}
\textbf{B} \textbf{C}
\textbf{C} \textbf{D}
Identify the major product \textbf{D}.
Options
- A.
6-Oxoheptanal
- B.
Heptane-1,6-diol
- C.
1-Methylcyclohexane-1,2-diol
- D.
Heptanedioic 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
Ozonolysis Fragmentation Patterns|Glycol Periodic Acid Cleavage|Tautomerism Conditions
Why This Question Is Tricky
Common Mistakes
The trap tests the student's ability to distinguish between standard reductions and reductive couplings.
Students who mistake \ce{Mg(Hg)} for a simple hydride donor (like \ce{NaBH4}) will predict the formation of heptane-1,6-diol.
Since \ce{HIO4} strictly requires a vicinal diol to form its cyclic periodate intermediate, the acyclic 1,6-diol would be inert.
Recognizing the Pinacol coupling is essential, as it generates the cyclic vicinal diol required to make the \ce{HIO4} step chemically active, ultimately creating a 'connectivity loop' that regenerates the original ozonolysis product.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Hydrocarbons - Class 11 Part 2 |
| Concept | Ozonolysis Fragmentation Patterns |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |