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Ch.9 - Molecular Geometry and Bonding Theories
Chapter 9, Problem 122a

Methyl isocyanate, CH3NCO, was made infamous in 1984 when an accidental leakage of this compound from a storage tank in Bhopal, India, resulted in the deaths of about 3800 people and severe and lasting injury to many thousands more. (a) Draw a Lewis structure for methyl isocyanate.

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Identify the total number of valence electrons in the molecule. Carbon (C) has 4, hydrogen (H) has 1, nitrogen (N) has 5, and oxygen (O) has 6. Calculate the total valence electrons for CH3NCO.
Determine the central atom. In this case, carbon (C) is often the central atom in organic molecules. Arrange the atoms in a reasonable structure: CH3 connected to NCO.
Draw single bonds between the central carbon and the surrounding atoms: C-H, C-N, and N-C-O. This uses up some of the valence electrons.
Distribute the remaining valence electrons to satisfy the octet rule for each atom, starting with the most electronegative atoms (O and N).
Adjust the structure to minimize formal charges, possibly by creating double or triple bonds, especially between C, N, and O, to ensure all atoms have a complete octet.

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Key Concepts

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

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 connectivity of atoms, allowing chemists to predict molecular geometry and reactivity. In drawing a Lewis structure, one must account for the total number of valence electrons and ensure that each atom achieves a stable electron configuration, typically resembling that of noble gases.
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Valence Electrons

Valence electrons are the outermost electrons of an atom and are crucial in determining how an atom bonds with others. The number of valence electrons influences an atom's reactivity and the types of bonds it can form. For example, carbon has four valence electrons, allowing it to form four covalent bonds, while nitrogen has five, enabling it to form three bonds and hold a lone pair.
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Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. It is determined by the number of bonding pairs and lone pairs of electrons around the central atom, which affects the molecule's shape and properties. Understanding molecular geometry is essential for predicting the behavior of molecules in chemical reactions and their interactions with other substances.
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Related Practice
Textbook Question
The organic molecules shown here are derivatives of benzene in which six-membered rings are 'fused' at the edges of the hexagons.

(e) Benzene, naphthalene, and anthracene are colorless, but tetracene is orange. What does this imply about the relative HOMO–LUMO energy gaps in these molecules? See the 'Chemistry Put to Work' box on orbitals and energy.
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Textbook Question

The organic molecules shown here are derivatives of benzene in which six-membered rings are 'fused' at the edges of the hexagons.

(b) Suppose you are given a sample of one of the compounds. Could combustion analysis be used to determine unambiguously which of the three it is?

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Open Question
Antibonding molecular orbitals can be used to make bonds to other atoms in a molecule. For example, metal atoms can use appropriate d orbitals to overlap with the π*2p orbitals of the carbon monoxide molecule. This is called d-π backbonding. (a) Draw a coordinate axis system in which the y-axis is vertical in the plane of the paper and the x-axis horizontal. Write 'M' at the origin to denote a metal atom. (b) Now, on the x-axis to the right of M, draw the Lewis structure of a CO molecule, with the carbon nearest the M. The CO bond axis should be on the x-axis. (c) Draw the CO π*2p orbital, with phases (see the 'Closer Look' box on phases) in the plane of the paper. Two lobes should be pointing toward M. (d) Now draw the dxy orbital of M, with phases. Can you see how they will overlap with the π*2p orbital of CO? (e) What kind of bond is being made with the orbitals between M and C, σ or π? (f) Predict what will happen to the strength of the CO bond in a metal–CO complex compared to CO alone.