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Ch.7 - Covalent Bonding and Electron-Dot Structures
Chapter 7, Problem 74

Acrylonitrile 1C3H3N2 is a molecule that is polymerized to make carpets and fabrics. The connections between atoms are shown. Lewis dot structure of acrylonitrile showing atom connections; identify the shortest bond.
(d) Identify the shortest bond in the molecule.

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1
Identify the types of bonds present in the acrylonitrile molecule. Look for single, double, and triple bonds.
Recall that bond length is inversely related to bond strength: triple bonds are shorter than double bonds, which are shorter than single bonds.
Examine the structure to locate any triple bonds. In acrylonitrile, the carbon-nitrogen bond is a triple bond.
Compare the lengths of the different bonds in the molecule. The C≡N bond is expected to be the shortest due to its triple bond nature.
Conclude that the shortest bond in the acrylonitrile molecule is the C≡N bond.

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Key Concepts

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

Bond Types

In chemistry, bonds between atoms can be classified as single, double, or triple bonds. Single bonds involve one pair of shared electrons, double bonds involve two pairs, and triple bonds involve three pairs. The type of bond affects the bond length and strength, with triple bonds being the shortest and strongest, followed by double and then single bonds.
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Bond Length

Bond length is the distance between the nuclei of two bonded atoms. It is influenced by the type of bond; shorter bonds typically indicate stronger interactions between atoms. In a molecule, the shortest bond is often the one that is either a double or triple bond, as these involve more shared electron pairs compared to single bonds.
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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 provide a visual representation of how atoms are connected and can help identify bond types and lengths. Analyzing a Lewis structure allows one to determine which bonds are present and to identify the shortest bond in the molecule.
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