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Polyhalogen Compounds

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why is vinyl chloride unreactive in nucleophilic substitution reactions

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Solution

Vinyl chloride (CH₂=CHCl) is unreactive in nucleophilic substitution reaction due to resonance. In vinyl chloride, the lone pair of electrons on chlorine is in resonance with the C-C double bond, because of which there is partial double bond character in C-Cl bond. Because of this double bond character, the C-Cl bond becomes stronger and hence difficult to break.

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Q. Allyl chloride is a .............. compound while vinyl chloride is inert towards nucleophilic substitution.

Q. Assertion :In comparison to ethyl chloride it is difficult to carry out nucleophilic substitution on vinyl chloride. Reason: Vinyl group is electron donating.

Q. Give reasons:
a) Alkyl halides are insoluble in water although they contain polar C-X bond.
b) Grignard reagent should be prepared under anhydrous condition.
c) Vinyl chloride is less reactive than ethyl chloride towards nucleophilic substitution reactions.

Q. Assertion :Vinylic halides are reactive towards nucleophilic substitution reaction.
Reason: Reactivity is due to the polarity of carbon-halogen bond.

Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The reaction is

(a) electrophilic elimination reaction

(b) electrophilic substitution reaction

(c) free radical addition reaction

(d) nucleophilic substitution reaction

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