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Lone Pair

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Organic Chemistry

Definition

A lone pair, also known as an unshared pair, refers to a pair of valence electrons in an atom that are not involved in covalent bonding with other atoms. These electron pairs are not shared with neighboring atoms and remain solely within the atom's electron cloud.

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5 Must Know Facts For Your Next Test

  1. Lone pairs can contribute to the overall shape and polarity of a molecule, as they occupy space and influence the arrangement of bonding pairs around the central atom.
  2. The presence of lone pairs on a central atom can lead to a distortion in the molecular geometry, resulting in a non-linear or bent shape, as seen in molecules like water (H$_2$O) and ammonia (NH$_3$).
  3. Lone pairs can participate in hydrogen bonding, a type of intermolecular attraction that plays a crucial role in the properties of many organic and biological molecules.
  4. The presence of lone pairs on the central atom in a nucleophilic species is essential for its ability to donate electrons and participate in polar reaction mechanisms.
  5. Lone pairs on the sulfur atom in the amino acid cysteine can participate in the formation of disulfide bridges, which are important for the stability and function of many proteins.

Review Questions

  • Explain how the presence of lone pairs on a central atom can influence the molecular geometry of a compound.
    • The presence of lone pairs on a central atom can lead to a distortion in the molecular geometry, as lone pairs occupy more space than bonding pairs. This results in a non-linear or bent shape for the molecule, as observed in compounds like water (H$_2$O) and ammonia (NH$_3$). The lone pairs repel each other and the bonding pairs, causing the molecule to adopt a geometry that minimizes this repulsion and maximizes the distance between the electron pairs.
  • Describe the role of lone pairs in the participation of a nucleophilic species in polar reaction mechanisms.
    • The presence of lone pairs on the central atom of a nucleophilic species is essential for its ability to donate electrons and participate in polar reaction mechanisms. The lone pairs provide the necessary electron density that can be shared with an electrophilic species, forming a new covalent bond. This electron-donating ability of the lone pairs is a key feature that allows nucleophiles to initiate and drive various types of polar reactions, such as nucleophilic substitutions and additions, which are crucial in organic chemistry.
  • Analyze the importance of lone pairs on the sulfur atom in the amino acid cysteine and their contribution to the stability and function of proteins.
    • The lone pairs on the sulfur atom in the amino acid cysteine can participate in the formation of disulfide bridges, which are important for the stability and function of many proteins. These disulfide bridges, formed by the oxidation of two cysteine residues, help to stabilize the three-dimensional structure of proteins by creating additional cross-links between polypeptide chains. The presence of these stabilizing disulfide bridges, facilitated by the lone pairs on the sulfur atoms, is crucial for maintaining the proper folding and functionality of various proteins involved in biological processes.

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