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Ch.8 - Covalent Compounds: Bonding Theories and Molecular Structure
Chapter 8, Problem 64

Oxaloacetic acid is an intermediate involved in the citric acid cycle of food metabolism. What is the hybridization of the various carbon atoms in oxaloacetic acid, and what are the approximate values of the various bond angles?Chemical structure of oxaloacetic acid showing carbon atoms and bond angles.

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1
Identify the structure of oxaloacetic acid from the image provided.
Determine the hybridization of each carbon atom by examining the number of sigma bonds and lone pairs around each carbon.
For each carbon atom, use the following rules: sp3 hybridization if it has 4 sigma bonds, sp2 hybridization if it has 3 sigma bonds and 1 pi bond, and sp hybridization if it has 2 sigma bonds and 2 pi bonds.
Estimate the bond angles based on the hybridization: approximately 109.5° for sp3, 120° for sp2, and 180° for sp.
Summarize the hybridization and bond angles for each carbon atom in the oxaloacetic acid molecule.

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Key Concepts

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

Hybridization

Hybridization is a concept in chemistry that describes the mixing of atomic orbitals to form new hybrid orbitals, which can explain the geometry of molecular bonding. In oxaloacetic acid, the carbon atoms can exhibit different hybridizations, such as sp2 for those involved in double bonds and sp3 for those with single bonds. Understanding hybridization helps predict the shape and bond angles of the molecule.
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Bond Angles

Bond angles are the angles formed between adjacent bonds in a molecule, which are influenced by the hybridization of the atoms involved. For example, sp3 hybridized carbons typically have bond angles of about 109.5 degrees, while sp2 hybridized carbons have bond angles of approximately 120 degrees. Knowing the bond angles is crucial for understanding the three-dimensional structure of molecules like oxaloacetic acid.
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Citric Acid Cycle

The citric acid cycle, also known as the Krebs cycle, is a key metabolic pathway that involves a series of chemical reactions used by all aerobic organisms to generate energy. Oxaloacetic acid plays a vital role as an intermediate in this cycle, combining with acetyl-CoA to form citric acid. Understanding this cycle provides context for the importance of oxaloacetic acid in cellular respiration and energy production.
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