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Question #44365
The Question
An optically inactive compound with the IUPAC name is subjected to oxidative cleavage using an excess of periodic acid (\ce{HIO4}) in an aqueous medium at 298 K. Which of the following statements correctly describes the stereochemical nature of the resulting organic product(s)?
Options
- A.
A single achiral compound is formed, and the product mixture is optically inactive.
- B.
A single chiral compound is formed, and the product mixture is optically active.
- C.
A racemic mixture of two enantiomers is formed, and the product mixture is optically inactive.
- D.
Two diastereomers are formed in unequal amounts, and the product mixture is optically active.
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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
Optical Activity and Enantiomers|Glycol Periodic Acid Cleavage
Why This Question Is Tricky
Common Mistakes
This question tests the 'Meso-Trap' in oxidative cleavage.
Students often assume that an optically inactive (meso) starting material must yield achiral products.
However, when a meso-diol with chiral centers outside the cleavage site is oxidized by \ce{HIO4}, the internal plane of symmetry is broken.
Because the two halves of the meso compound are mirror images, their cleavage yields exactly one molecule of the (R)-enantiomer and one molecule of the (S)-enantiomer.
This results in a 1:1 racemic mixture.
The absence of alpha-hydrogens prevents enolization, ensuring the racemic mixture is the direct kinetic result of the cleavage.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Haloalkanes and Haloarenes - Class 12 |
| Concept | Optical Activity and Enantiomers |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |