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Ch.8 - Covalent Compounds: Bonding Theories and Molecular Structure
Chapter 8, Problem 8

Use the chemical structure for Tagamet, a drug used to treatpeptic ulcers and heartburn, to answer questions 8 and 9.Chemical structure of Tagamet highlighting bond 1 for hybridization questions.
Which orbitals overlap to form bond 1? (LO 8.5)(a) s bond: N 1sp22 with C 1sp22; p bond: N (p) with C (p)(b) N 1sp22 with C 1sp22(c) s bond: N 1sp22 with C 1sp22; p bond: N 1sp22 withC 1sp22(d) s bond: N (sp) with C 1sp22; p bond: N (p) with C (p)

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1
Identify the atoms involved in bond 1. In this case, bond 1 is between a carbon (C) and a nitrogen (N) atom.
Determine the hybridization of the carbon atom in bond 1. Since the carbon is involved in a double bond, it is sp2 hybridized.
Determine the hybridization of the nitrogen atom in bond 1. The nitrogen is also sp2 hybridized because it is involved in a double bond and has one lone pair.
Identify the types of orbitals that overlap to form the sigma (σ) bond. The sigma bond is formed by the overlap of sp2 hybrid orbitals from both the carbon and nitrogen atoms.
Identify the types of orbitals that overlap to form the pi (π) bond. The pi bond is formed by the side-by-side overlap of unhybridized p orbitals from both the carbon and nitrogen atoms.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hybridization

Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. In the context of bond formation, it helps explain the geometry and bond angles in molecules. For example, sp² hybridization involves one s orbital and two p orbitals, resulting in three equivalent orbitals arranged in a trigonal planar shape, which is crucial for understanding the bonding in organic compounds.
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Orbital Overlap

Orbital overlap refers to the interaction of atomic orbitals from two atoms to form a chemical bond. The extent of overlap determines the strength of the bond; greater overlap leads to stronger bonds. In covalent bonding, an s orbital can overlap with another s or p orbital, while p orbitals can overlap with each other, forming sigma (σ) and pi (π) bonds, respectively, which are essential for understanding molecular structure.
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Types of Bonds

In chemistry, bonds can be classified into sigma (σ) and pi (π) bonds. Sigma bonds are formed by the head-on overlap of orbitals, allowing for free rotation around the bond axis, while pi bonds result from the side-to-side overlap of p orbitals, restricting rotation. Understanding these types of bonds is crucial for analyzing molecular geometry and reactivity, particularly in complex organic molecules like Tagamet.
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