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Question #43951
The Question
Compound \textbf{X}, methyl 4-acetylbenzoate, is reacted with one equivalent of aniline () 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 , catalytic (pH 4.5), 298 K \textbf{P} \item \textbf{Condition II:} Excess , dilute aqueous (pH = 1.0), 373 K \textbf{Q} \item \textbf{Condition III:} Excess , aqueous acetate buffer (pH = 4.5), 298 K \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
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
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
| Subject | Chemistry |
| Chapter | Aldehydes, Ketones, and Carboxylic Acids - Class 12 |
| Concept | Schiff Base pH Dependence |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |