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Ch.23 - Organic and Biological Chemistry
Chapter 23, Problem 77

Draw an orbital overlap picture of methane (CH₄) with the carbon in sp3 hybridization and an orbital overlap picture of a molecule with carbon in sp2 hybridization. Explain why the carbon atom in methane is more stable in sp3 hybridization than in sp2 hybridization.

Verified step by step guidance
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Step 1: Understand the concept of hybridization. In chemistry, hybridization is the process of combining atomic orbitals into new hybrid orbitals suitable for the pairing of electrons to form chemical bonds. For carbon, sp3 hybridization involves the mixing of one s orbital and three p orbitals, resulting in four equivalent sp3 hybrid orbitals.
Step 2: Draw the orbital overlap picture for methane (CH₄) with carbon in sp3 hybridization. In this configuration, carbon forms four sp3 hybrid orbitals, each overlapping with the 1s orbital of a hydrogen atom, creating four sigma (σ) bonds. This results in a tetrahedral geometry with bond angles of approximately 109.5°.
Step 3: Draw the orbital overlap picture for a molecule with carbon in sp2 hybridization. In sp2 hybridization, carbon mixes one s orbital and two p orbitals to form three sp2 hybrid orbitals, leaving one unhybridized p orbital. The sp2 orbitals form sigma bonds, while the unhybridized p orbital can participate in pi (π) bonding, resulting in a trigonal planar geometry with bond angles of 120°.
Step 4: Compare the stability of sp3 and sp2 hybridization in carbon. The sp3 hybridization in methane allows for maximum overlap of orbitals, leading to strong sigma bonds and a stable tetrahedral structure. In contrast, sp2 hybridization involves pi bonds, which are generally weaker than sigma bonds, making the structure less stable compared to sp3 hybridization.
Step 5: Conclude why methane is more stable with sp3 hybridization. The tetrahedral geometry of sp3 hybridization in methane minimizes electron repulsion and maximizes bond strength, contributing to its stability. In contrast, the presence of pi bonds in sp2 hybridization introduces additional electron repulsion and weaker bonding, making it less stable than sp3 hybridization.