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Haloalkanes and Haloarenes question

2021 · 18 Mar · Shift 2 · Q4
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Haloalkanes and Haloarenes question

2021 · 18 Mar · Shift 2 · Q4

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Given below are two statements : Statement I : C2H5OHC_2H_5OHC2​H5​OH and AgCNAgCNAgCN both can generate nucleophile. Statement II : KCNKCNKCN and AgCNAgCNAgCN both will generate nitrile nucleophile with all reaction conditions. Choose the most appropriate option :
  1. A
    Statement I is false but statement II is true.
  2. B
    Both statement I and statement II are true.
  3. C
    Both statement I and statement II are false.
  4. D
    Statement I is true but statement II is false.
View written solutionFree

Correct answer: D

  1. Analyze Statement I

    Statement I: $$C_2H_5OHandandandAgCNbothcangeneratenucleophile. both can generate nucleophile.bothcangeneratenucleophile.

    • For C2H5OHC_2H_5OHC2​H5​OH: Ethanol has lone pairs on oxygen, so it can act as a neutral nucleophile.
    • For AgCNAgCNAgCN: Silver cyanide is largely covalent. In reactions, the cyanide group is not freely available as CN−CN^-CN− in the same way as ionic cyanides, but the species can still participate through the cyanide group. In haloalkane reactions, AgCNAgCNAgCN leads mainly to isocyanide formation due to attack via nitrogen.

    Hence, both can generate/provide nucleophilic attack.

    Therefore, Statement I is true.

  2. Analyze Statement II

    Statement II: $KCN$ and $AgCN$ both will generate nitrile nucleophile with all reaction conditions.

    • KCNKCNKCN is ionic and gives free CN−CN^-CN−, which is an ambident nucleophile. In alkyl halide substitution, carbon-end attack predominates, giving nitriles (R−C≡NR-C\equiv NR−C≡N).
    • AgCNAgCNAgCN is covalent, so free CN−CN^-CN− is not available. In reactions with alkyl halides, attack occurs mainly through nitrogen, giving isocyanides (R−N≡CR-N\equiv CR−N≡C), not nitriles.

    So it is incorrect to say both generate nitrile nucleophile with all reaction conditions.

    Therefore, Statement II is false.

  3. Choose the correct option

    • Statement I: True
    • Statement II: False

    So the correct option is: D\boxed{\text{D}}D​

  4. Compare with stored correct answer

    Stored correct answer: D

    My derived answer matches the stored answer.

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