DISTINGUISH BETWEEN CHLOROBENZENE & BENZYLCHLORIDE .

First get ionic salt example by KOH given by benzyl chloride only then test from salt analysis

unique feature of chlorobenzene 1)partial double bond character(2)cl attach to sp2 bybridise (3) arenes are electron rich thus more repulsion (4) c-cl bond is less polar than benzyl chloride (5)resonance

C6H5Cl is chlorobenzene. The chlorine atom has replaced one oh the hydrogens on the benzene ring. In benzyl chloride you have CH2 group attached to the ring with a chlorine atom on the other end of the CH2 group to complete the form bonds for the carbon in the CH2 group - C6H5CH2Cl.

1) Take both the compounds in a test tube. Add 1 - 2 ml of aqueous KOH to each of the test tubes. Acidify with dilute HNO3 and add AgNO3. Benzyl chloride gives white precipitate while chlorobenzene does not.
2) in benzyl chloride, cl is attached to sp3 hybridised carbon atom while in chlorobenzene it is attached to sp2. 
3)  chlorobenzene is not soluble in water while benzyl chloride is slightly. 
4) boiling point of chlorobenzene is higher 
5) melting point of benzyl chloride is higher

cholorobenzene goes under conjugation 

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