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Question #45066

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following sequence of chemical evaluations at 298 K:

\textbf{Step 1:} The basic strength of five substituted anilines is compared with aniline in an aqueous medium: 2-methylaniline, 4-methylaniline, 2,6-dimethylaniline, 4-nitroaniline, and 4-methoxyaniline. Let XX be the number of amines from this set that are strictly \textit{less} basic than aniline.

\textbf{Step 2:} 4-Methylaniline (Compound A, given pKapK_a of its conjugate acid =5.0= 5.0) undergoes condensation with benzaldehyde to form a Schiff base.

\textbf{Step 3:} The rate of this Schiff base formation is highly pH-dependent and reaches a maximum at an optimal pH, denoted as YY. At this optimal pH, the concentration of the protonated amine [AH+][AH^+] is exactly 10 times the concentration of the unprotonated amine [A][A].

\textbf{Step 4:} Let ZZ be the total number of sp2sp^2 hybridized carbon atoms in the final Schiff base product.

Calculate the value of (X×Y)+Z(X \times Y) + Z.

Options

  • A.

    17

  • B.

    25

  • C.

    29

  • D.

    31

Check Your Answer

Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Mechanism_Trap

Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.

Concepts Behind This Question

Acidity and Basicity (pKa/pKb)|Schiff Base pH Dependence

Why This Question Is Tricky

Common Mistakes

The primary trap is the 'Ortho Effect' in anilines.

Students typically associate alkyl groups with electron donation (+I, +HC), expecting ortho/para-methylanilines to be more basic than aniline.

However, ortho-substitution causes Steric Inhibition of Protonation (SIP), destabilizing the solvated conjugate acid and making 2-methylaniline and 2,6-dimethylaniline less basic than aniline.

A secondary trap involves the pH dependence of Schiff base formation; students might blindly apply the Henderson-Hasselbalch equation backwards or fail to recognize that at the optimal pH (~4.0), the majority of the amine is actually protonated, but the small equilibrium concentration of the free amine is sufficient for the rate-determining nucleophilic attack.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterOrganic Chemistry – Some Basic Principles and Techniques - Class 11 Part 2
ConceptAcidity and Basicity (pKa/pKb)
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree