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Haloalkanes and Haloarenes question

2021 · 17 Mar · Shift 2 · Q5
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  5. /2021 · 17 Mar · Shift 2 · Q5

Haloalkanes and Haloarenes question

2021 · 17 Mar · Shift 2 · Q5

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
The correct pair(s) of the ambident nucleophiles is(are) (A) AgCNAgCNAgCN/KCNKCNKCN (B) RCOOAgRCOOAgRCOOAg/RCOOKRCOOKRCOOK (C) AgNO2AgNO_2AgNO2​/KNO2KNO_2KNO2​ (D) AgIAgIAgI/KIKIKI
  1. A
    (B) and (C) only
  2. B
    (B) only
  3. C
    (A) and (C) only
  4. D
    (A) only
View written solutionFree

Correct answer: C

  1. Concept: ambident nucleophile

An ambident nucleophile is a nucleophile that can attack through two different atoms. Examples:

  • CN−CN^-CN− : can attack through C or N
  • NO2−NO_2^-NO2−​ : can attack through N or O

In such cases, the product may differ depending on the reagent used, especially with silver salts vs potassium salts.


  1. Check each pair

(A) AgCN/KCNAgCN/KCNAgCN/KCN

The nucleophile involved is CN−CN^-CN−, which is ambident.

  • With KCNKCNKCN, ionic character is higher, so attack occurs mainly through carbon, giving nitriles: R−C≡NR-C\equiv NR−C≡N.
  • With AgCNAgCNAgCN, bonding is more covalent/polymeric, and attack occurs through nitrogen, giving isocyanides: R−N≡CR-N\equiv CR−N≡C.

So, (A) is correct.


(B) RCOOAg/RCOOKRCOOAg/RCOOKRCOOAg/RCOOK

The nucleophile is carboxylate ion RCOO−RCOO^-RCOO−. Although it has two oxygen atoms, they are equivalent by resonance and it does not behave as the standard ambident nucleophile giving two distinct constitutional products via different donor atoms in this context.

So, (B) is not correct.


(C) AgNO2/KNO2AgNO_2/KNO_2AgNO2​/KNO2​

The nucleophile is NO2−NO_2^-NO2−​, which is ambident.

  • With KNO2KNO_2KNO2​, attack occurs through O, giving alkyl nitrites: R−ONOR-ONOR−ONO.
  • With AgNO2AgNO_2AgNO2​, attack occurs through N, giving nitroalkanes: R−NO2R-NO_2R−NO2​.

So, (C) is correct.


(D) AgI/KIAgI/KIAgI/KI

The nucleophile is I−I^-I−, which can attack only through iodine. It is not ambident.

So, (D) is not correct.


  1. Correct pair(s)

The correct pairs are:

(A) and (C)(A) \text{ and } (C)(A) and (C)

Hence, the correct option is:

C\boxed{\text{C}}C​
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