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Ch.8 - Covalent Compounds: Bonding Theories and Molecular Structure
Chapter 8, Problem 111

In the cyanate ion, OCN-, carbon is the central atom.(d) Which hybrid orbitals are used by the C atom, and how many p bonds does the C atom form?

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Identify the valence electrons for each atom in the OCN- ion. Carbon (C) has 4 valence electrons, Oxygen (O) has 6, and Nitrogen (N) has 5. Additionally, consider the extra electron from the negative charge of the ion.
Determine the total number of valence electrons available for bonding in the OCN- ion. Sum the valence electrons from each atom and include the additional electron from the negative charge.
Predict the molecular structure of OCN- using the valence shell electron pair repulsion (VSEPR) theory. Arrange the atoms to minimize repulsion between electron pairs.
Determine the hybridization of the carbon atom. Based on the arrangement of electron pairs around carbon, predict whether it uses sp, sp2, or sp3 hybrid orbitals.
Identify the types of bonds formed by the carbon atom. Look at the molecular structure and determine how many sigma (σ) bonds and pi (π) bonds are formed by carbon with the adjacent 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 process of combining atomic orbitals to form new hybrid orbitals that can accommodate the bonding requirements of an atom. In the case of carbon in the cyanate ion (OCN-), the carbon atom undergoes sp hybridization, which involves the mixing of one s orbital and one p orbital to create two equivalent sp hybrid orbitals.
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Hybridization

Bonding and p Bonds

In covalent bonding, p bonds are formed when two atomic orbitals overlap sideways, allowing for the sharing of electrons. In the cyanate ion, the carbon atom forms one p bond with the nitrogen atom and another p bond with the oxygen atom, contributing to the overall structure and stability of the ion.
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Lewis Structures

Lewis structures are diagrams that represent the bonding between atoms in a molecule and the lone pairs of electrons that may exist. They help visualize the arrangement of electrons and the types of bonds (single, double, or triple) present. For the cyanate ion, drawing the Lewis structure reveals the hybridization and the number of p bonds formed by the carbon atom.
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Related Practice
Textbook Question

Carbon monoxide is produced by incomplete combustion of fossil fuels. (b) Do you expect CO to be paramagnetic or diamagnetic?

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Textbook Question

Carbon monoxide is produced by incomplete combustion of fossil fuels. (c) What is the bond order of CO? Does this match the bond order predicted by the electron-dot structure?

Textbook Question
Make a sketch showing the location and geometry of thep orbitals in the nitrite ion, NO2-. Describe the bonding inthis ion using a localized valence bond model for s bondingand a delocalized MO model for p bonding.
Textbook Question
The dichromate ion, Cr2O72-, has neither Cr¬Cr nor O¬O bonds. (b) How many outer-shell electrons does each Cr atom have in your electron-dot structure? What is the likely geometry around the Cr atoms?
Textbook Question

Cyclooctatetraene dianion, C8H82-, is an organic ion with the structure shown. Considering only the p bonds and not the s bonds, cyclooctatetraene dianion can be described by the following energy diagrams of its p molecular orbitals:

(a) What is the hybridization of the 8 carbon atoms?

Textbook Question

Cyclooctatetraene dianion, C8H82-, is an organic ion with the structure shown. Considering only the p bonds and not the s bonds, cyclooctatetraene dianion can be described by the following energy diagrams of its p molecular orbitals:

(b) Three of the p molecular orbitals are bonding, three are antibonding, and two are nonbonding, meaning that they have the same energy level as isolated p orbitals. Which is which?