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Action of alcoholic AgNO(3) on chloroben...

Action of alcoholic `AgNO_(3)` on chlorobenzene is similar to the action on -

A

Allyl chloride

B

Vinyl chloride

C

Isopropyl chloride

D

Benzyl chloride

Text Solution

AI Generated Solution

The correct Answer is:
To determine which compound exhibits behavior similar to the action of alcoholic AgNO₃ on chlorobenzene, we need to analyze the reactivity of the chlorine atom in each option provided. The key point is that chlorobenzene does not readily lose its chloride ion due to the resonance stabilization of the aromatic ring. ### Step-by-Step Solution: 1. **Understand the Reaction of Chlorobenzene with Alcoholic AgNO₃**: - Chlorobenzene is an aromatic compound where the chlorine atom is attached to a benzene ring. The resonance effect stabilizes the bond between the carbon and chlorine, making it difficult to remove the chloride ion (Cl⁻) and thus preventing the formation of a white precipitate of AgCl. 2. **Evaluate the First Option: Allyl Chloride (CH₂=CH-CH₂Cl)**: - Allyl chloride has a chlorine atom attached to a carbon that is part of a double bond (vinylic carbon). The presence of the double bond means that the chlorine is less stable compared to chlorobenzene, and it can be removed more easily. Therefore, allyl chloride does not exhibit similar behavior to chlorobenzene. **Hint**: Check if the chlorine is attached to a saturated or unsaturated carbon. 3. **Evaluate the Second Option: Vinyl Chloride (CH₂=CHCl)**: - Vinyl chloride has the chlorine attached to a vinylic carbon, which is also unsaturated. Similar to allyl chloride, the chlorine can be removed more easily due to the lack of resonance stabilization. Thus, vinyl chloride does not show similar behavior to chlorobenzene. **Hint**: Consider the stability of the carbon-chlorine bond in the presence of double bonds. 4. **Evaluate the Third Option: Isopropyl Chloride (CH₃-CHCl-CH₃)**: - Isopropyl chloride has the chlorine attached to a saturated carbon. The absence of resonance stabilization means that the chlorine can be removed more easily, leading to the formation of a white precipitate with AgNO₃. Therefore, isopropyl chloride does not exhibit similar behavior to chlorobenzene. **Hint**: Identify if the carbon attached to chlorine is part of a double bond or not. 5. **Evaluate the Fourth Option: Benzyl Chloride (C₆H₅-CH₂Cl)**: - Benzyl chloride has the chlorine attached to a saturated carbon (CH₂) that is directly bonded to a benzene ring. While the carbon is saturated, the resonance from the benzene ring provides some stabilization to the carbon-chlorine bond. However, benzyl chloride can still lose the chloride ion more readily than chlorobenzene due to the influence of the benzene ring, but it does not behave like chlorobenzene. **Hint**: Analyze the influence of the aromatic ring on the stability of the carbon-chlorine bond. 6. **Conclusion**: - After evaluating all options, the compound that shows behavior similar to chlorobenzene in terms of the action of alcoholic AgNO₃ is **Vinyl Chloride**. Both chlorobenzene and vinyl chloride do not readily lose their chloride ions due to resonance stabilization. ### Final Answer: The action of alcoholic AgNO₃ on chlorobenzene is similar to the action on **Vinyl Chloride**.
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