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Ch.7 - Covalent Bonding and Electron-Dot Structures
Chapter 7, Problem 92

Some mothballs used when storing clothes are made of naphthalene (C10H8), which has the following incomplete structure. Incomplete Lewis dot structure of naphthalene for bonding analysis.
(a) Add double bonds where needed to draw a complete electron-dot structure.

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Identify the incomplete structure of naphthalene (C10H8) in the image provided.
Recognize that naphthalene is an aromatic hydrocarbon with a fused ring structure.
Recall that each carbon atom in an aromatic ring should have a total of four bonds (including hydrogen atoms).
Add double bonds between carbon atoms to ensure each carbon has four bonds, forming alternating single and double bonds in the rings.
Verify that the final structure has alternating double bonds in both rings, ensuring the aromaticity of the naphthalene molecule.

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Key Concepts

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

Lewis Dot Structures

Lewis dot 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 valence electrons and lines to represent covalent bonds. Understanding how to draw these structures is essential for visualizing molecular geometry and predicting reactivity.
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Covalent Bonding

Covalent bonding occurs when two atoms share one or more pairs of electrons, allowing them to achieve a full outer electron shell. In organic compounds like naphthalene, carbon atoms typically form four covalent bonds, leading to complex structures. Recognizing how to identify and represent these bonds is crucial for constructing accurate molecular representations.
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Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In naphthalene, the double bonds can be arranged in multiple configurations, which helps explain its stability and reactivity. Understanding resonance is important for predicting the behavior of aromatic compounds in chemical reactions.
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Related Practice
Textbook Question
The estimated lattice energy for CsF21s2 is +2347 kJ/mol. Use the data given in Problem 6.86 to calculate an overall energy change in kilojoules per mole for the formation of CsF21s2 from its elements. Does the overall reaction absorb energy or release it? In light of your answer to Problem 6.86, which compound is more likely to form in the reaction of cesium with fluorine, CsF or CsF2?

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Textbook Question
Benzene has the following structural formula.

(b) Which statement best describes the carbon–carbon bonds in benzene? (i) Three carbon–carbon bonds are longer and weaker than the other three carbon–carbon bonds. (ii) All six carbon–carbon bonds are identical, and their length and strength are between a double and single bond. (iii) The length of carbon–carbon double bond switches back and forth between the length of a double and a single bond.
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Textbook Question
Draw three resonance structures for sulfur tetroxide, SO4, whose connections are shown below. (This is a neutral mol-ecule; it is not a sulfate ion.) Assign formal charges to the atoms in each structure.
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Textbook Question
Four different structures (a), (b), (c), and (d) can be drawn for compounds named dibromobenzene, but only three different compounds actually exist. Explain. (a)

(b)

(c)

(d)

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Textbook Question
Use the following information plus the data given in Tables 6.2 and 6.3 to calculate the second electron affinity, Eea2, of oxygen. Is the O2-ion stable in the gas phase? Why is it stable in solid MgO? Heat of sublimation for Mg1s2 = +147.7 kJ/mol Bond dissociation energy for O21g2 = +498.4 kJ/mol Eea1 for O1g2 = -141.0 kJ/mol Net energy change for formation of MgO(s) from its elements = -601.7 kJ/mol
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Textbook Question

Assign formal charges to the atoms in the following structures. Which of the two do you think is the more important contributor to the resonance hybrid?(a)(b)

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