Question

A compound on treatment with NaOH followed by addition
of AgNO₃ produces white precipitate at room
temperature. The precipitate is soluble in NH₄OH . The
compound is identified as
(a) vinyl chloride (b) benzyl chloride
(c) chlorobenzene (d) ethyl bromide

Answer 1

The compounds is benzyl chloride.

option (B) is correct.

Explanation:

• AgNO3 solution can be used to find out which halogen is present in a suspected halogenoalkane.
• NaOH substitutes the Cl- from haloalkane.  
• In Chlorobenzene and Vinyl chloride, the Cl is in conjugation with benzene ring and does not give alcohol.  
• In Benzyl chloride, the Cl is not directly linked to benzene and thus react as haloalkane and gives white precipitate of AgCl with AgNO3  ​which is soluble in NH4 OH.
• Ethyl bromide gives yellow precipitate of AgBr which is insoluble in NH4OH at room temperature.

Thus the compounds is benzyl chloride.

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Conversion from acetylene to chlorobenzene  ?

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