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Question #44476
The Question
An organic compound () exhibits terminal acidity. Two separate experiments are performed on 1 mole of :
\textbf{Experiment 1:} is subjected to vigorous oxidation with hot acidic , yielding a carboxylic acid and a gas. The reaction consumes moles of .
\textbf{Experiment 2:} is treated with to undergo complete hydration, forming a stable tautomer . Compound is then subjected to vigorous oxidation with hot acidic , yielding exclusively the major product as dictated by Popoff's rule. This oxidation step consumes moles of .
Assuming complete conversion in all steps, what are the values of and , and the identity of ?
Options
- A.
, , = Acetic acid
- B.
, , = Propanoic acid
- C.
, , = Acetic acid
- D.
, , = Propanoic acid
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Numerical_Precision
Improve calculation stamina and avoid rounding errors in high-stakes competitive examinations.
Concepts Behind This Question
Alkynes Terminal Acidity|Tautomerism Conditions|Equivalent Concept in Redox
Why This Question Is Tricky
Common Mistakes
This problem tests the intersection of kinetic/thermodynamic organic pathways with rigorous redox stoichiometry.
A common student trap is assuming that since hydration merely adds water (which has no net oxidation state change), the subsequent oxidation of the ketone will consume the same equivalents of oxidant as the direct oxidation of the alkyne (leading to Option B).
However, the regioselectivity of ketone cleavage (Popoff's rule) dictates a different carbon-carbon bond breaking (C2-C3) compared to the alkyne cleavage (C1-C2).
This fundamentally alters the final oxidation states of the products, dropping the n-factor from 8 to 6.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Hydrocarbons - Class 11 Part 2 |
| Concept | Alkynes Terminal Acidity |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |