Why is water considered an excellent nucleophile?

Prepare for the UofT BCH210H1 Biochemistry I midterm with exam-like questions. Access detailed solutions and explanations for proteins, lipids, and metabolism topics. Strengthen your understanding and excel on test day!

Water is considered an excellent nucleophile primarily because it can donate the lone pairs on the oxygen atom. In the structure of a water molecule (H2O), the oxygen atom possesses two lone pairs of electrons. These lone pairs can readily participate in chemical reactions, particularly nucleophilic attacks, where they can form bonds with electrophilic centers (electron-deficient species).

The ability of water to act as a nucleophile is largely attributed to the high electronegativity of oxygen, which pulls the electron density towards itself and creates a partial negative charge on the oxygen atom. This partial negative charge enhances the nucleophilicity of water, making it more capable of attacking electrophilic sites.

Additionally, water's polarity allows it to solvate cations and anions, further increasing its reactivity in biological and chemical processes. However, the key aspect here is its ability to donate the lone pairs on oxygen, which makes it such an effective nucleophile in various biochemical reactions, including those that occur during metabolism.

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