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Question #44883

Difficulty: 8/10 | 🟢 Free

The Question

Consider the hydrocarbon $\mathbf{X}$ , 1-methylcyclohex-1-ene. It undergoes two distinct oxidative pathways under different conditions:

Pathway I: $\mathbf{X} \xrightarrow{KMnO_4, \ H^+, \ \Delta} \mathbf{P}$

Pathway II: $\mathbf{X} \xrightarrow{KMnO_4, \ OH^-, \ 273 \ K} \mathbf{Q} \xrightarrow{HIO_4} \mathbf{R}$

Identify the major organic products $\mathbf{P}$ and $\mathbf{R}$ .

Options

A.
$\mathbf{P}$ = 6-oxoheptanoic acid; $\mathbf{R}$ = 6-oxoheptanal
B.
$\mathbf{P}$ = 6-oxoheptanal; $\mathbf{R}$ = 6-oxoheptanoic acid
C.
$\mathbf{P}$ = 6-oxoheptanoic acid; $\mathbf{R}$ = 6-oxoheptanoic acid
D.
$\mathbf{P}$ = 1-methylcyclohexane-1,2-diol; $\mathbf{R}$ = 6-oxoheptanal

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

KMnO₄ Redox pH Dependency|Glycol Periodic Acid Cleavage|Oxidation State Traps

Why This Question Is Tricky

Common Mistakes

The question tests the critical distinction between thermodynamic (vigorous) oxidative cleavage and controlled sequential cleavage.

Students often conflate the outcomes of hot acidic $KMnO_4$ with $O_3/Zn$ or $OsO_4/NaIO_4$ .

The 'hidden variable' is the susceptibility of the intermediate aldehyde to further oxidation.

Acidic $KMnO_4$ possesses sufficient oxidation potential to convert the intermediate aldehyde to a carboxylic acid, whereas $HIO_4$ cleavage of a glycol stops at the aldehyde stage.

Choosing the wrong option indicates a failure to account for the pH and temperature dependence of $KMnO_4$ 's oxidizing power.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	D and F Block Elements - Class 12
Concept	KMnO₄ Redox pH Dependency
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free