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Question #44479

Difficulty: 8/10 | 🟢 Free

The Question

An organic compound $\mathbf{X}$ , (4-nitrophenyl)(phenyl)methane, is subjected to Friedel-Crafts alkylation using 1-chloro-2,2-dimethylpropane in the presence of a stoichiometric excess of anhydrous $\ce{AlCl3}$ at $298\text{ K}$ . Assuming thermodynamic and kinetic factors strongly favor a single major product $\mathbf{Y}$ , identify the correct IUPAC name of $\mathbf{Y}$ .

Options

A.
(4-(2-methylbutan-2-yl)phenyl)(4-nitrophenyl)methane
B.
(4-(2,2-dimethylpropyl)phenyl)(4-nitrophenyl)methane
C.
(3-(2-methylbutan-2-yl)phenyl)(4-nitrophenyl)methane
D.
phenyl(2-(2-methylbutan-2-yl)-4-nitrophenyl)methane

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

Friedel-Crafts Alkylation Limitations|Resonance Energy and Stability|Electrophile vs Nucleophile

Why This Question Is Tricky

Common Mistakes

This problem tests the hierarchy of Electrophilic Aromatic Substitution (EAS) and carbocation stability.

The 'Hidden Variable' is the dual-ring system where students must recognize that a strongly deactivated ring (nitro-substituted) acts as a spectator, violating the naive assumption that any aromatic ring will react.

Furthermore, it traps students who fail to account for the mandatory 1,2-methyl shift of the neopentyl system, preventing the formation of the kinetically expected but thermodynamically impossible primary alkylbenzene.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Hydrocarbons - Class 11 Part 2
Concept	Friedel-Crafts Alkylation Limitations
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free