For the reaction: The correct statement from the following is:
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
For the reaction:
The correct statement from the following is:
- a✓
The transition state formed in the above reaction is less polar than the localised anion.
- b
The reaction can occur in acetic acid also.
- c
The solvent used in the reaction solvates the ions formed in rate determining step.
- d
Br can act as competing nucleophile.
The transition state formed in the above reaction is less polar than the localised anion.
Step 1: Identify the reaction
This appears to be an iodide exchange reaction (Finkelstein-type):
Wait, this is the same compound on both sides. Let me reconsider.
Actually, this might be showing isotopic exchange or the mechanism of with iodide.
Mechanism:
Step 2: Analyze the transition state
transition state:
- Trigonal bipyramidal geometry
- Partial bonds to both incoming and leaving I
- Negative charge delocalized over two iodine atoms
Localized anion (reactant):
- Free ion
- Full negative charge on single iodine
- More polar (concentrated charge)
Transition state:
- Charge spread over larger area (two I atoms)
- Less polar than localized anion
Statement (a) is TRUE ✓
Step 3: Evaluate other statements
(b) "The reaction can occur in acetic acid also."
- Acetic acid is polar protic solvent
- Strongly solvates anions (H-bonding)
- is slower in protic solvents
- Acetone (polar aprotic) is much better
- Statement is misleading/false ✗
(c) "The solvent used in the reaction solvates the ions formed in rate determining step."
- Acetone is polar aprotic
- Does NOT strongly solvate anions (no H-bonding)
- This is why it's good for (nucleophile is "naked")
- Statement is FALSE ✗
(d) "Br can act as competing nucleophile."
- Not relevant to this specific reaction
- No Br mentioned in the reaction
- Statement is irrelevant/false ✗
Answer: (a)
Key Concepts:
Transition State:
- Charge delocalization
- Less polar than separated ions
- Stabilized by charge dispersal
Solvent Effects:
| Solvent Type | Examples | Effect on | |--------------|----------|------------------| | Polar aprotic | Acetone, DMSO, DMF | Fast (doesn't solvate Nu⁻) | | Polar protic | H₂O, ROH, RCOOH | Slow (solvates Nu⁻) |
Finkelstein Reaction:
- Halogen exchange using NaI in acetone
- Driven by precipitation of NaCl/NaBr
- mechanism
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