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 110

Chapter 7, Problem 110

Propose structures for molecules that meet the following descriptions. (b) Contains an N atom that has one p bond and two s bonds

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Identify the type of hybridization of the nitrogen atom based on the number and types of bonds it forms. Since the nitrogen atom forms one pi (π) bond and two sigma (σ) bonds, it is sp2 hybridized.

Understand that in sp2 hybridization, one of the three sp2 orbitals is used to form a pi bond, and the other two are involved in forming sigma bonds.

Consider the common molecular structures that involve sp2 hybridized nitrogen. A typical example is an imine group, where nitrogen is double-bonded to a carbon atom (C=N) and also bonded to two other groups (which could be hydrogen or alkyl groups) via single bonds.

Sketch a structure where the nitrogen is double bonded to a carbon atom. This accounts for the pi bond. Then, add two more groups (like hydrogen or alkyl groups) attached to the nitrogen with single bonds, representing the sigma bonds.

Verify the valency and formal charges to ensure the stability and feasibility of the proposed structure. The nitrogen should have three bonds and one lone pair, maintaining a neutral charge in typical organic structures.

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Key Concepts

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

Hybridization

Hybridization is the concept that describes the mixing of atomic orbitals to form new hybrid orbitals, which can explain the geometry and bonding properties of molecules. In this case, the nitrogen atom is likely sp² hybridized, which allows for one p bond and two s bonds, resulting in a trigonal planar arrangement.

Bonding Types

Understanding the types of chemical bonds is crucial for molecular structure. A p bond refers to a pi bond, which is formed by the sideways overlap of p orbitals, while s bonds refer to sigma bonds formed by the head-on overlap of orbitals. In the proposed structure, the nitrogen atom will have one pi bond and two sigma bonds.

Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms in a molecule. The presence of one p bond and two s bonds around the nitrogen atom suggests a specific geometry, likely trigonal planar, which influences the overall shape and reactivity of the molecule. This geometry is determined by the hybridization and the types of bonds formed.

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Related Practice

Textbook Question

Calculate an approximate heat of combustion for ethane (C2H6) in kilojoules by using the bond dissocation energies in Table 9.3. (The strength of the O'O bond is 498 kJ/ mol, and that of a C ' O bond in CO2 is 804 kJ/mol.)

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)

Textbook Question

Draw the resonance structure indicated by the curved arrows. Assign formal charges, and evaluate which of the two structures is a larger contributor to the resonance hybrid.

Textbook Question

The dichromate ion, Cr2O72-, has neither Cr¬Cr nor O¬O bonds. (a) Taking both 4s and 3d electrons into account, draw an electron-dot structure that minimizes the formal charges on the atoms.

Textbook Question

In the cyanate ion, OCN-, carbon is the central atom.(b) Which resonance structure makes the greatest contributionto the resonance hybrid? Which makes the leastcontribution? Explain.

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