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Ch.1 - Structure and Bonding
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoWade 9th EditionCh.1 - Structure and BondingProblema 18
Capitolo 1, Problema 18

Predict the hybridization, geometry, and bond angles for the carbon and nitrogen atoms in acetonitrile (CH3–C≡N:).

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Identify the structure of acetonitrile, which is CH3C≡N. The molecule consists of a methyl group (CH3) attached to a carbon-nitrogen triple bond.
Determine the hybridization of the carbon atom in the methyl group (CH3). The carbon is bonded to three hydrogen atoms and one other carbon atom, making a total of four sigma bonds. This suggests sp3 hybridization.
Determine the geometry around the sp3 hybridized carbon atom in the methyl group. With sp3 hybridization, the geometry is tetrahedral, and the bond angles are approximately 109.5 degrees.
Examine the carbon atom in the carbon-nitrogen triple bond (C≡N). This carbon is involved in one sigma bond with the nitrogen and one sigma bond with the adjacent carbon, along with two pi bonds. This indicates sp hybridization.
Determine the geometry around the sp hybridized carbon and nitrogen atoms in the C≡N group. The geometry is linear, with bond angles of 180 degrees, due to the sp hybridization.

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Hybridization

Hybridization is the process of mixing atomic orbitals to form new hybrid orbitals, which can form sigma bonds or accommodate lone pairs. In acetonitrile, the carbon atom bonded to nitrogen is sp hybridized, resulting in a linear geometry, while the carbon in the methyl group is sp3 hybridized, leading to a tetrahedral geometry.
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Using bond sites to predict hybridization

Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms in a molecule. For acetonitrile, the carbon-nitrogen triple bond results in a linear geometry around the sp hybridized carbon and nitrogen atoms, while the sp3 hybridized carbon in the methyl group has a tetrahedral geometry.
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Molecular Geometry Explained.

Bond Angles

Bond angles are the angles between adjacent bonds in a molecule. In acetonitrile, the sp hybridized carbon and nitrogen atoms form a linear structure with a bond angle of 180 degrees. The sp3 hybridized carbon in the methyl group has bond angles of approximately 109.5 degrees, typical for a tetrahedral geometry.
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