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Benzyl chloride undergoes nucleophilic s...

Benzyl chloride undergoes nucleophilic substitution much more easily than chlorobenzene. Explain.

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Benzyl chloride undergoes nucleophilic substitution readily via resonance stabilised benzyl carbocation.

On the otherhand C-Cl bond in benzene has partial double bond character due to resonance and hence is difficult to cleave.
Hence, benzyl chloride undergoes nucleophilic substitution much more easily than chlorobenzene.
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AAKASH SERIES-ALKYL AND ARYL HALIDES-OBJECTIVE EXERCISE - 4 (ASSERTION (A) & REASON (R) TYPE QUESTIONS)
  1. Benzyl chloride undergoes nucleophilic substitution much more easily t...

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  2. (A) Towards SN2 reaction, order of reactivity is CH3Br > CH3CH2Br > (C...

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  3. (A) Pure chloroform does not give precipitate with AgNO3 solution. (...

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  4. (A) Addition of bromine to 2-butene yields 2,3-dibromobutane. (R) Br...

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  5. (A) Thionyl chloride reacts with primary alcohols to form pure alkyl h...

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  6. (A) The boiling points of alkyl halides decrease in the order RI > RBr...

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  7. (A) KCN reacts with methyl chloride to give methyl cyanide and methyl ...

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  8. (A) In monohaloarenes, further electrophilic substitution occurs at or...

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  9. (A) Benzonitrile is prepared by the action of chlorobenzene with KCN ...

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  10. (A) Styrene on reaction with HBr gives 1-bromo-1-phenyl ethane. (R) ...

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  11. (A) NBS is a specific reagent for allylic bromination (R) Allylic br...

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  12. (A) Benzyl bromide when kept in acetone - water, produces benzyl alcoh...

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  13. (A) 2-Bromobutane on reaction with sodium ethoxide in ethanol gives 1-...

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  14. (A) Chloral reacts with phenyl chloride to form DDT (R) It is an ele...

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  15. (A) CH3overset(Cl)overset(|)(C)HCH2CH3overset(Alc.KOH)(rarr)CH3CH=CHCH...

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  16. (A) Addition of HBr on but-2-ene gives two structural isomeric product...

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  17. (A) The nature of the solvent can influence the rotation of plane pola...

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  18. (A) SN2 reactions are exothermic (R) SN2 reactions are thermochemica...

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  19. (A) Chloroform can be used as general anaesthetic. (R) In presence o...

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  20. (A) Ethyl chloride gives C2H5CN as major product with alc. KCN but C2H...

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