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Question #43951

Difficulty: 8/10 | 🟢 Free

The Question

Compound \textbf{X}, methyl 4-acetylbenzoate, is reacted with one equivalent of aniline (\cePhNH2\ce{PhNH2}) under three distinct sets of conditions to yield the major organic equilibrium products \textbf{P}, \textbf{Q}, and \textbf{R} respectively (excluding aniline derivatives if unreacted or protonated):

\begin{itemize} \item \textbf{Condition I:} Anhydrous \ceMgSO4\ce{MgSO4}, catalytic \ceCH3COOH\ce{CH3COOH} (pH ≈\approx 4.5), 298 K →\rightarrow \textbf{P} \item \textbf{Condition II:} Excess \ceH2O\ce{H2O}, dilute aqueous \ceHCl\ce{HCl} (pH = 1.0), 373 K →\rightarrow \textbf{Q} \item \textbf{Condition III:} Excess \ceH2O\ce{H2O}, aqueous acetate buffer (pH = 4.5), 298 K →\rightarrow \textbf{R} \end{itemize}

Identify \textbf{P}, \textbf{Q}, and \textbf{R}.

Options

  • A.

    \textbf{P}: Methyl 4-(1-(phenylimino)ethyl)benzoate; \textbf{Q}: 4-acetylbenzoic acid; \textbf{R}: Methyl 4-acetylbenzoate

  • B.

    \textbf{P}: Methyl 4-(1-(phenylimino)ethyl)benzoate; \textbf{Q}: 4-acetylbenzoic acid; \textbf{R}: Methyl 4-(1-(phenylimino)ethyl)benzoate

  • C.

    \textbf{P}: Methyl 4-(1-(phenylimino)ethyl)benzoate; \textbf{Q}: 4-(1-(phenylimino)ethyl)benzoic acid; \textbf{R}: Methyl 4-acetylbenzoate

  • D.

    \textbf{P}: 4-(1-(phenylimino)ethyl)benzoic acid; \textbf{Q}: 4-acetylbenzoic acid; \textbf{R}: 4-(1-(phenylimino)ethyl)benzoic acid

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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

Schiff Base pH Dependence|Esterification Reversibility

Why This Question Is Tricky

Common Mistakes

This question tests the 'Schiff Base Paradox' and the critical distinction between kinetic and thermodynamic control.

Students often memorize that 'pH 4.5 is optimal for Schiff base formation' and erroneously apply it to predict product formation in aqueous media (Condition III), ignoring that pH 4.5 only optimizes the rate (kinetic control).

Without water removal, the thermodynamic equilibrium heavily favors the reactants.

Additionally, it tests the reversibility of esterification under harsh aqueous acidic conditions (Condition II) versus its stability under mild or anhydrous conditions.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterAldehydes, Ketones, and Carboxylic Acids - Class 12
ConceptSchiff Base pH Dependence
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree