Nucleophilic Attack

Definition

Nucleophilic attack is a fundamental chemical reaction in which a nucleophile, an electron-rich species, attacks an electrophilic (electron-deficient) center, forming a new covalent bond. This process is central to understanding many organic reactions, including polar reactions, addition reactions, and substitution reactions.

5 Must Know Facts For Your Next Test

1. Nucleophilic attack is a key step in many organic reactions, including additions, substitutions, and eliminations.
2. The strength of a nucleophile is determined by its ability to donate electrons, which is influenced by factors such as electronegativity and polarizability.
3. Nucleophilic attack can occur at saturated or unsaturated carbon centers, leading to the formation of new carbon-carbon or carbon-heteroatom bonds.
4. The stereochemistry of the product in a nucleophilic addition reaction is determined by the orientation of the nucleophile's approach to the electrophilic center.
5. Nucleophilic attack on conjugated systems, such as in the electrophilic addition to conjugated dienes, can result in the formation of stabilized allylic carbocations.

Review Questions

• Explain how the concept of nucleophilic attack is related to the topic of polar covalent bonds and electronegativity.
  • The concept of nucleophilic attack is closely linked to the idea of polar covalent bonds and electronegativity. Polar covalent bonds arise due to differences in electronegativity between atoms, leading to the development of partial charges. Nucleophiles, being electron-rich species, are attracted to these partially positively charged, electrophilic centers and can undergo nucleophilic attack to form new bonds. The strength of a nucleophile is determined by its ability to donate electrons, which is influenced by factors such as electronegativity and polarizability.
• Describe how the mechanism of nucleophilic attack is used to understand the addition of HBr to ethylene, a classic example of a polar reaction.
  • In the addition of HBr to ethylene, the reaction proceeds through a polar mechanism involving nucleophilic attack. The hydrogen atom of HBr, being the more electropositive species, acts as an electrophile and is attracted to the electron-rich double bond of ethylene. The bromine atom, being the more electronegative species, acts as a nucleophile and attacks the partially positively charged carbon atom, leading to the formation of the final product, 2-bromoethane. The use of curved arrows in the reaction mechanism helps visualize the flow of electrons during the nucleophilic attack, demonstrating how the breaking and forming of bonds is accompanied by the development of partial charges.
• Analyze how the concept of nucleophilic attack is applied to understand the stereochemistry of the addition of water to a chiral alkene, as well as the hydration of alkynes.
  • The stereochemistry of the addition of water to a chiral alkene is determined by the orientation of the nucleophilic attack. The oxygen atom of water acts as a nucleophile and approaches the electrophilic carbon of the alkene, leading to the formation of a new carbon-oxygen bond. The stereochemistry of the product is dictated by the relative positioning of the nucleophile and the substituents on the alkene. Similarly, in the hydration of alkynes, the nucleophilic attack of water on the triple bond results in the formation of a new carbon-oxygen bond, with the specific stereochemistry of the product depending on the orientation of the nucleophilic attack. Understanding the principles of nucleophilic attack is crucial for predicting and explaining the stereochemical outcomes of these polar addition reactions.

Related terms

Nucleophile: A nucleophile is a species that donates electrons and attacks electrophilic centers, forming new bonds.

Electrophile: An electrophile is a species that is attracted to electron-rich areas and accepts electrons during a reaction.

Polar Reaction: A polar reaction is a reaction in which the breaking and forming of bonds is accompanied by the development of partial charges.