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Ch.10 - Chemical Bonding I: The Lewis Model
Chapter 10, Problem 95

Carbon ring structures are common in organic chemistry. Draw a Lewis structure for each carbon ring structure, including any necessary resonance structures. a. C4H8 b. C4H4 c. C6H12 d. C6H6

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1
Identify the molecular formula for benzene, which is C_6H_6, indicating it is a six-carbon ring with alternating double bonds.
Recognize that benzene is a planar, cyclic molecule with a hexagonal ring structure, where each carbon atom is bonded to one hydrogen atom.
Draw a hexagon to represent the carbon ring, and place a carbon atom at each vertex of the hexagon.
Add alternating double bonds between the carbon atoms in the ring to represent the delocalized pi electrons, which is a key feature of benzene's resonance.
Draw resonance structures by shifting the position of the double bonds around the ring, showing that the electrons are delocalized across the entire structure.

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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 use dots to represent electrons and lines to represent bonds between atoms. Understanding how to draw Lewis structures is essential for visualizing molecular geometry and predicting reactivity.
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Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In molecules like benzene (C6H6), resonance structures help depict the equal distribution of electron density across the carbon atoms, which contributes to the molecule's stability and unique properties. Recognizing resonance is crucial for understanding the behavior of organic compounds.
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Hydrocarbons

Hydrocarbons are organic compounds consisting entirely of hydrogen and carbon. They can be classified into aliphatic (straight or branched chains) and aromatic (ring structures) categories. Benzene, a common aromatic hydrocarbon, has a cyclic structure with alternating double bonds, which is important for understanding its chemical properties and reactions in organic chemistry.
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Related Practice
Textbook Question

In the Chemistry and the Environment box on free radicals in this chapter, we discussed the importance of the hydroxyl radical in reacting with and eliminating many atmospheric pollutants. However, the hydroxyl radical does not clean up everything. For example, chlorofluorocarbons—which destroy stratospheric ozone—are not attacked by the hydroxyl radical. Consider the hypothetical reaction by which the hydroxyl radical might react with a chlorofluorocarbon: OH(g) + CF2Cl2(g) → HOF(g) + CFCl2(g) Use bond energies to explain why this reaction is improbable. (The C–F bond energy is 552 kJ/mol.)

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Textbook Question

Write an appropriate Lewis structure for each compound. Make certain to distinguish between ionic and molecular compounds. b. ClF5

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Textbook Question

Each compound contains both ionic and covalent bonds. Write ionic Lewis structures for each, including the covalent structure for the ion in brackets. Write resonance structures if necessary. a. BaCO3

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Textbook Question

Amino acids are the building blocks of proteins. The simplest amino acid is glycine (H2NCH2COOH). Draw a Lewis structure for glycine. (Hint: The central atoms in the skeletal structure are nitrogen and the two carbon atoms. Each oxygen atom is bonded directly to the right-most carbon atom.)

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Textbook Question

Formic acid is responsible for the sting of ant bites. By mass, formic acid is 26.10% C, 4.38% H, and 69.52% O. The molar mass of formic acid is 46.02 g/mol. Determine the molecular formula of formic acid and draw its Lewis structure.

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Textbook Question

Diazomethane is a highly poisonous, explosive compound because it readily evolves N2. Diazomethane has the following composition by mass: 28.57% C; 4.80% H; and 66.64% N. The molar mass of diazomethane is 42.04 g/mol. Find the molecular formula of diazomethane, draw its Lewis structure, and assign formal charges to each atom. Why is diazomethane not very stable? Explain.

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