Start Learning Free

Before You Begin

Question #45062

Difficulty: 8/10 | 🟢 Free

The Question

Evaluate the following four statements regarding the reactivity of carbonyl compounds towards nucleophilic addition. Assign a value of 1 if the statement is True, and 0 if it is False.

S1S_1: The drastically lower rate of nucleophilic addition to di-tert-butyl ketone compared to formaldehyde is primarily because the electromeric polarization (E effect) of the \ce{C=O} π\pi-bond is completely absent in hindered ketones. S2S_2: Acetophenone fails to form a crystalline bisulfite adduct with saturated aqueous \ce{NaHSO3} at 298 K primarily because severe steric crowding makes the formation of the sp3sp^3 hybridized adduct highly unfavorable. S3S_3: The equilibrium constant (KeqK_{eq}) for cyanohydrin formation is drastically lower for di-tert-butyl ketone than for acetone due to the severe steric strain (B-strain) between the bulky tert-butyl groups in the sp3sp^3 hybridized product. S4S_4: Cyclohexanone forms a crystalline bisulfite adduct with aqueous \ce{NaHSO3} more readily than 3-pentanone, because the cyclic structure 'ties back' the alkyl chains, significantly reducing steric hindrance in the transition state.

Consider the truth values as a 4-bit binary number S1S2S3S4S_1 S_2 S_3 S_4. What is the decimal equivalent of this binary number?

Options

  • A.

    7

  • B.

    15

  • C.

    6

  • D.

    3

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

Electromeric Effect|Nucleophilic Addition Sterics

Why This Question Is Tricky

Common Mistakes

The question tests the 'Nucleophilic Addition Sterics' exception.

Students often over-rely on electronic effects, falsely assuming that a lack of reactivity implies an absence of the electromeric effect (S1S_1 trap).

The framework highlights that the electromeric effect is theoretically present, but the reaction is kinetically suppressed by steric hindrance.

Furthermore, S2S_2 and S4S_4 test critical exceptions to the 'methyl ketone rule' for bisulfite addition, emphasizing the dominance of steric volume (B-strain and conformational tying-back) over simple functional group categorization.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterOrganic Chemistry – Some Basic Principles and Techniques - Class 11 Part 2
ConceptElectromeric Effect
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree