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Ch.7 - Covalent Bonding and Electron-Dot Structures
Chapter 7, Problem 85d

Draw as many resonance structures as you can for the following nitrogen-containing compounds. Not all will obey the octet rule. Use curved arrows to depict the conversion of one structure into another. (d) N2O3(ONNO2)

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Identify the Lewis structure of N<sub>2</sub>O<sub>3</sub>. Start by arranging the atoms where nitrogen and oxygen are bonded in a way that satisfies the typical valences (N typically forms three bonds, O typically forms two bonds).
Determine the formal charges on each atom in the initial structure to ensure the most stable arrangement of electrons. Remember that the sum of the formal charges should equal the overall charge of the molecule (which is neutral in this case).
Use curved arrows to show the movement of electrons to form different resonance structures. Move electrons from areas of higher electron density (like lone pairs or double bonds) to adjacent atoms or bonds that can accept electrons.
Create additional resonance structures by changing the locations of double bonds and lone pairs while keeping the connectivity of the atoms the same. Ensure that each structure still follows the rules of chemical bonding, although not all structures may obey the octet rule.
Review all the drawn resonance structures to ensure they are valid. Each structure should have atoms with complete valence shells where possible, except where the octet rule is not obeyed, and formal charges should be minimized.

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Key Concepts

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

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. They are used to represent molecules where a single Lewis structure cannot adequately depict the electron distribution. Each resonance structure contributes to the overall hybrid structure, which is a more accurate representation of the molecule's actual electron configuration.
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Octet Rule

The octet rule is a chemical guideline stating that atoms tend to bond in such a way that they each have eight electrons in their valence shell, achieving a stable electron configuration similar to that of noble gases. While many elements follow this rule, some, particularly transition metals and heavier elements, can have expanded octets or may not complete their octet, leading to exceptions in resonance structures.
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Curved Arrows in Resonance

Curved arrows are a notation used in organic chemistry to show the movement of electrons during the formation of resonance structures. The tail of the arrow indicates the starting point of the electron pair, while the head points to where the electrons are moving. This visual representation helps in understanding how different resonance forms are interrelated and how electron delocalization occurs within a molecule.
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Related Practice
Textbook Question
Calculate the energy change in kilojoules per mole when lithium atoms lose an electron to bromine atoms to form isolated Li+ and Br-ions. [The Ei for Li1g2 is 520 kJ/mol; the Eea for Br1g2 is -325 kJ/mol.] Will a lithium atom transfer an elec-tron to a bromine atom to form isolated Li+ 1g2 and Br-1g2 ions? Explain.
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Textbook Question
Ibuprofen 1C13H18O22, marketed under such brand names as Advil and Motrin, is a drug sold over the counter for treatment of pain and inflammation. Complete the structure of ibuprofen by adding hydrogen atoms and lone pairs where needed.

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Textbook Question

Draw as many resonance structures as you can for the following nitrogen-containing compounds. Not all will obey the octet rule. Use curved arrows to depict the conversion of one structure into another. (b) NO

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Textbook Question
Which of the following pairs of structures represent resonance forms, and which do not? (a)
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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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