Before You Begin
Question #44628
The Question
An alkyl halide () is subjected to dehydrohalogenation under two different sets of conditions:
Reaction 1: (Major) Reaction 2: (Major)
Reductive ozonolysis of yields a mixture of two carbonyl compounds; one gives both a positive Tollens' test and a positive iodoform test, while the other gives a negative Tollens' test. Reductive ozonolysis of yields two carbonyl compounds, one of which is a gas at and the other gives a positive iodoform test.
What is the absolute difference in the number of hyperconjugative -hydrogens between the major products and ?
Options
- A.
2
- B.
3
- C.
4
- D.
6
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
E1/E2 Solvent and Base Effects|E2 Regioselectivity (Saytzeff vs Hoffmann)
Why This Question Is Tricky
Common Mistakes
The question tests the E2 regioselectivity competition between thermodynamic (Saytzeff) and kinetic (Hoffmann) control.
Students often blindly apply Saytzeff's rule.
The 'hidden variable' is the steric bulk of the base (), which raises the activation energy for internal proton abstraction.
This forces the reaction to yield the anti-Saytzeff product.
The problem rigorously integrates qualitative organic analysis (Tollens'/Iodoform tests) to prevent guessing the substrate, ensuring a deep, multi-step mechanistic understanding.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Haloalkanes and Haloarenes - Class 12 |
| Concept | E1/E2 Solvent and Base Effects |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |