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Question #44141
The Question
2,6-Dimethylbenzoic acid () and benzoic acid () are subjected to esterification studies. Under standard Fischer esterification conditions (excess \ce{EtOH}, catalytic \ce{H2SO4}, 298 K), fails to react due to severe steric hindrance. To achieve the esterification of , it is first dissolved in 100% \ce{H2SO4} to generate a reactive intermediate , which is subsequently treated with cold ethanol. When and are dissolved in 100% \ce{H2SO4}, their cryoscopic van't Hoff factors are observed to be and , respectively. Identify the correct values of and , the hybridization of the electrophilic carbon in , and the primary thermodynamic driving force for the formation of over a standard protonated species.
Options
- A.
, , , Relief of B-Strain
- B.
, , , Hyperconjugation
- C.
, , , Steric Inhibition of Resonance
- D.
, , , Redox-neutral cyclization
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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
Electron Transfer Accounting|Nucleophilic Acyl Substitution|Esterification Reversibility|Steric Hindrance (B-Strain)
Why This Question Is Tricky
Common Mistakes
The question tests the 'Chemical Exception' of the ortho effect in esterification.
Students often blindly apply Fischer esterification kinetics and assume simple protonation () for all carboxylic acids in sulfuric acid.
The hidden variable is the steric hindrance (B-Strain) that prevents the formation of the tetrahedral intermediate, forcing the molecule to undergo dehydration to a linear hybridized acylium ion.
This changes the electron transfer accounting, resulting in an anomalous van't Hoff factor of 4 instead of 2.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Redox Reactions - Class 11 Part 2 |
| Concept | Electron Transfer Accounting |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |