Ch.7 - Covalent Bonding and Electron-Dot Structures

McMurry8th EditionChemistryISBN: 9781292336145Not the one you use?Change textbook

McMurry 8th Edition

Ch.7 - Covalent Bonding and Electron-Dot Structures

Problem 86

Chapter 7, Problem 86

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

Verified step by step guidance

Identify the structures given in the problem and draw them if necessary.

Understand that resonance forms are different Lewis structures for the same molecule that differ only in the positions of electrons, not the positions of atoms.

Check if the structures have the same molecular formula and the same arrangement of atoms.

Examine the electron distribution: look for differences in the placement of electrons, such as lone pairs and pi bonds, between the structures.

Determine if the structures can be interconverted by moving electrons (using curved arrows) without breaking any sigma bonds. If they can, they are resonance forms.

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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 the electron distribution cannot be depicted by a single Lewis structure. Each resonance form contributes to the overall hybrid structure, which is a more accurate representation of the molecule's actual electron distribution.

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 are essential for visualizing how atoms are connected and how electrons are arranged. Understanding how to draw and interpret Lewis structures is crucial for identifying resonance forms, as they provide the foundational representation of the molecule.

Delocalization of Electrons

Delocalization of electrons refers to the phenomenon where electrons are spread over several atoms rather than being localized between two atoms. This occurs in molecules with conjugated systems or multiple bonds, allowing for greater stability. Recognizing delocalization is key to understanding resonance, as it explains why certain structures can be represented in multiple ways without changing the overall connectivity of the atoms.

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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

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.