Chemistry Haloalkanes and Haloarenes 1 Mark
Appeared in: 2026 (3 sets)
Assertion (A) : Aromatic primary amines can be prepared by Gabriel Phthalimide synthesis. Reason (R) : Aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide.
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Question Analysis: Assertion (A) and Reason (R) based on NCERT Chemistry Class 12, Chapter: Amines.

Step 1 (Conceptual Foundation): [0.25 Mark]
Gabriel phthalimide synthesis involves the nucleophilic substitution of an alkyl halide by the phthalimide anion. The reaction mechanism is $S_N2$. The general reaction is:

$$ \text{Phthalimide} + \text{KOH} \rightarrow \text{Potassium Phthalimide} \xrightarrow{R-X} N\text{-Alkylphthalimide} \xrightarrow{H_3O^+} \text{Primary Amine} $$

Step 2 (Step-by-Step Logical Deduction): [0.50 Mark]

  • Assertion (A): Aromatic primary amines (like aniline) cannot be prepared by this method because aryl halides ($Ar-X$) do not undergo nucleophilic substitution with the phthalimide anion under normal conditions. Thus, Assertion (A) is False.
  • Reason (R): Aryl halides possess partial double bond character due to resonance, and the carbon atom is $sp^2$ hybridized, making the $C-X$ bond stronger and shorter. Additionally, the electron-rich benzene ring repels the nucleophile. Thus, Reason (R) is True.

Step 3 (Final Concluded Answer): [0.25 Mark]
Since Assertion (A) is False and Reason (R) is True, the correct option is: (d) Assertion (A) is false but Reason (R) is true.

💡 EL10 Concept Insight: Think of the aryl halide like a door that is bolted shut because of the benzene ring's special structure; the phthalimide "key" isn't strong enough to force it open, so the reaction simply won't happen.