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Ch.9 - Chemical Bonding I: The Lewis Model
All textbooksTro 4th EditionCh.9 - Chemical Bonding I: The Lewis ModelProblem 95
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Chapter 9, Problem 95

Draw the Lewis structure for nitric acid, ensuring the hydrogen atom is attached to one of the oxygen atoms. Include all three resonance structures by alternating the double bond among the three oxygen atoms. Use formal charge to determine which of the resonance structures is most important to the structure of nitric acid.

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1
Identify the total number of valence electrons in nitric acid (HNO₃). Hydrogen has 1, nitrogen has 5, and each oxygen has 6, giving a total of 24 valence electrons.
Draw the skeletal structure of HNO₃ with nitrogen as the central atom, bonded to one hydrogen and three oxygen atoms. Initially, connect each atom with single bonds.
Distribute the remaining valence electrons to satisfy the octet rule for each atom, starting with the outer atoms (oxygen) and then the central atom (nitrogen).
Create double bonds between nitrogen and one of the oxygen atoms to satisfy the octet rule for nitrogen. Repeat this process to form the three resonance structures by alternating the double bond among the three oxygen atoms.
Calculate the formal charge for each atom in all three resonance structures. The most stable resonance structure will have the formal charges closest to zero, with negative charges on the more electronegative atoms (oxygen).
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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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NaCl has a lattice energy of -787 kJ/mol. Consider a hypothetical salt XY. X3+ has the same radius of Na+ and Y3- has the same radius as Cl-. Estimate the lattice energy of XY.

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Open Question
Phosgene (Cl2CO) is a poisonous gas used as a chemical weapon during World War I. It is a potential agent for chemical terrorism today. Draw the Lewis structure of phosgene, including all three resonance forms by alternating the double bond among the three terminal atoms. Which resonance structure is the best?
Textbook Question

The cyanate ion (OCN-) and the fulminate ion (CNO-) share the same three atoms but have vastly different properties. The cyanate ion is stable, while the fulminate ion is unstable and forms explosive compounds. The resonance structures of the cyanate ion are explored in Example 9.8. Draw Lewis structures for the fulminate ion—including possible resonance forms— and use formal charge to explain why the fulminate ion is less stable (and therefore more reactive) than the cyanate ion.

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Textbook Question

Draw the Lewis structure for each organic compound from its condensed structural formula. b. CH3OCH3

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