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Out of the various possible isomers of C_(7)H_(7)Cl containing a benzene ring, suggest the structure with the weakest C-Cl bond. |
Answer» Solution :Four isomers are possible: their STRUCTURE are:  Just as in CHLOROBENZENE, the C-Cl bond is a pure single bond. Hence, out of the four isomers, the C-Cl bond is the weakest in benzyl chloride. Alternatively, the cleavage of C-Cl bond in benzyl chloride gives benzyl cation which is stabilized by RESONANCE.  On the order hand, cleavage of C-Cl bond in o-, m- or p-chlorotoluenes gives toyl cation which is highly unstable. as a result, the energy of activation for the cleavage of C-Cl bond in benzyl chloride is much SMALLER that that of C-Cl bond in o-, m-or p-chlorotoluenes. CONSEQUENTLY, the C-Cl bond o- , m-or p-chlorotoluenes. Consequently, the C-cl bond is the weakest in benzyl chloride. |
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