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Question #44857

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following reaction sequences starting with toluene (\ce{C6H5CH3}):

Sequence I: \ce{C6H5CH3} →2. \ceH3O+1. \ceCrO2Cl2, \ceCS2\xrightarrow[2. \ \ce{H3O^+}]{1. \ \ce{CrO2Cl2}, \ \ce{CS2}} PP →\ceHNO3/\ceH2SO4, 298 K\xrightarrow{\ce{HNO3} / \ce{H2SO4}, \ 298 \ \text{K}} P′P' (Major)

Sequence II: \ce{C6H5CH3} →2. \ceH3O+1. \ceWO2Cl2, \ceCS2\xrightarrow[2. \ \ce{H3O^+}]{1. \ \ce{WO2Cl2}, \ \ce{CS2}} QQ →\ceHNO3/\ceH2SO4, 298 K\xrightarrow{\ce{HNO3} / \ce{H2SO4}, \ 298 \ \text{K}} Q′Q' (Major)

Assume QQ is the recovered organic substrate if no oxidation occurs. Identify the major products P′P' and Q′Q'.

Options

  • A.

    P′P' = 3-Nitrobenzaldehyde, Q′Q' = 1-Methyl-4-nitrobenzene

  • B.

    P′P' = 3-Nitrobenzaldehyde, Q′Q' = 3-Nitrobenzoic acid

  • C.

    P′P' = 4-Nitrobenzaldehyde, Q′Q' = 1-Methyl-4-nitrobenzene

  • D.

    P′P' = 1-Methyl-4-nitrobenzene, Q′Q' = 3-Nitrobenzaldehyde

Check Your Answer

Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Exception_Exposure

Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.

Concepts Behind This Question

Variable Oxidation State Stability|Stability of High O.S. Fluorides/Oxides|d-orbital contraction

Why This Question Is Tricky

Common Mistakes

This question tests the student's understanding of periodic trends in oxidation state stability for transition metals versus p-block elements.

A common trap is misapplying the 'Inert Pair Effect' to the d-block, leading students to assume that heavier 5d elements (like W) are less stable in high oxidation states and thus stronger oxidants than 3d elements (like Cr).

If a student falls for this, they will incorrectly assume \ce{WO2Cl2} is a super-oxidant that oxidizes toluene to benzoic acid, leading them to choose the distractor containing 3-Nitrobenzoic acid.

It also rigorously tests Electrophilic Aromatic Substitution (EAS) regioselectivity.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterD and F Block Elements - Class 12
ConceptVariable Oxidation State Stability
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree