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NCERT Exemplar · Q21

Q.Nucleophile is a species that should have (Note: more than one of the given options may be correct.)

(i) a pair of electrons to donate
(ii) positive charge
(iii) negative charge
(iv) electron deficient species
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A nucleophile is "nucleus-loving" and must possess electrons to donate to electron-deficient centres. The defining requirement is a pair of electrons to donate, though negative charge often enhances nucleophilicity.

The term nucleophile comes from "nucleus-loving"—a species attracted to positive or electron-poor regions. To understand what makes something a nucleophile, we need to think about what happens during bond formation.

When a nucleophile attacks an electrophile, it forms a new covalent bond. A covalent bond requires two electrons, and in a nucleophilic attack, both electrons come from the nucleophile. This is the heart of nucleophilicity: the ability to donate an electron pair.

Let's examine each option:

  1. Option (i): A pair of electrons to donate

    This is the fundamental requirement. A nucleophile must have a lone pair or a π-bond that can be donated to form a new σ-bond with an electrophile. Examples include:

    • OHX−\ce{OH^-} (hydroxide ion with three lone pairs)
    • NHX3\ce{NH3} (ammonia with one lone pair)
    • HX2O\ce{H2O} (water with two lone pairs)
    • CNX−\ce{CN^-} (cyanide ion)

    Without an electron pair to donate, a species cannot act as a nucleophile. This is essential.

  2. Option (ii): Positive charge

    A positively charged species has lost electrons, making it electron-deficient. Such species are electrophiles, not nucleophiles. For instance, HX+\ce{H^+}, NOX2X+\ce{NO2^+}, and carbocations are all electrophiles that accept electron pairs rather than donate them.

    This is incorrect.

  3. Option (iii): Negative charge

    Negatively charged species have extra electrons, making them excellent electron donors. Anions like ClX−\ce{Cl^-}, BrX−\ce{Br^-}, OHX−\ce{OH^-}, and CNX−\ce{CN^-} are strong nucleophiles. The negative charge increases electron density and enhances the tendency to donate electrons.

    However, this is not required. Neutral molecules like NHX3\ce{NH3}, HX2O\ce{H2O}, and R−NHX2\ce{R-NH2} are also nucleophiles because they possess lone pairs. Negative charge makes a species a better nucleophile but is not mandatory.

    This is often true but not necessary.

  4. Option (iv): Electron deficient species …

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