CHEMISTRY:MOLECULAR..(LL)-PRINT..W/CODE
7th Edition
ISBN: 9781119457282
Author: JESPERSEN
Publisher: WILEY
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Textbook Question
Chapter 9, Problem 46RQ
What is a delocalized MO? Explain, in terms of orbital overlap, why delocalized MOs are able to form in the benzene molecule.
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The concept of valence-shell electron-pair repulsion
(VSEPR) is presented in introductory organic chemistry
as a way to predict molecular geometries. The idea be-
hind VSEPR is that areas of electron density repel each
other so that the geometry of bonds and/or lone pairs
of electrons around any one atom places these areas as
far apart as possible. For four areas of electron density,
a tetrahedral geometry is predicted. For three areas of
electron density, a trigonal planar geometry is predicted.
Two areas of electron density lead to a linear geometry.
VSEPR is simply a predictive tool, but in some
cases, it gives an incorrect prediction. In these
instances, additional insights into bonding are
necessary, such as resonance. Interestingly, several
important situations are critical to biochemistry where
VSEPR breaks down. Two examples are shown here.
:O:
CH3
H,N
H3N
CH3 H
:0:
:0:
Histidine
The circled nitrogen atoms are predicted by VSEPR
to be tetrahedral in geometry because each…
1.
a) Draw the dominant Lewis structure for the allene molecule (1,2-propyl diene, CH2CCH2 ) and use VSEPR theory to determine the molecule's geometry. In specifying the geometry give all bond angles and specify which nuclei lie in the same plane.
b) Propose a hybridization and bonding scheme for the atoms in allene. That is, specify how each of the atoms is hybridized, which atomic orbitals overlap to form bonding molecular orbitals, and the nature (i.e., sigma", pi, etc.) of these molecular orbitals.
c) Draw a plausible valence molecular orbital level diagram for allene (include only bonding MOs) based on the results from (b).
d) Based on the work from (c) deduce the valence electronic configuration of the ground state of allene.
e) Is the molecule planar or nonplanar? Explain your answer
Answer subparts c, d, and e
1.
a) Draw the dominant Lewis structure for the allene molecule (1,2-propyl diene, CH2CCH2 ) and use VSEPR theory to determine the molecule's geometry. In specifying the geometry give all bond angles and specify which nuclei lie in the same plane.
b) Propose a hybridization and bonding scheme for the atoms in allene. That is, specify how each of the atoms is hybridized, which atomic orbitals overlap to form bonding molecular orbitals, and the nature (i.e., 0", 7f, etc.) of these molecular orbitals.
c) Draw a plausible valence molecular orbital level diagram for allene (include only bonding MOs) based on the results from (b).
d) Based on the work from (c) deduce the valence electronic configuration of the ground state of allene.
e) Is the molecule planar or nonplanar? Explain your answer
Chapter 9 Solutions
CHEMISTRY:MOLECULAR..(LL)-PRINT..W/CODE
Ch. 9 - Practice Exercise 9.1 Label the shapes of the...Ch. 9 - Practice Exercise 9.2 What is the shape of the...Ch. 9 - Practice Exercise 9.3
What shape is expected for...Ch. 9 - Practice Exercise 9.4 The first known compound of...Ch. 9 - Practice Exercise 9.5
What shape is expected for...Ch. 9 - Practice Exercise 9.6 What shape is expected for...Ch. 9 - Practice Exercise 9.7 Is the sulfur tetrafluoride...Ch. 9 - Practice Exercise 9.8 Explain how you decided...Ch. 9 - Practice Exercise 9.9 Use the principles of VB...Ch. 9 - Practice Exercise 9.10 The phosphine molecule,...
Ch. 9 - Practice Exercise 9.11
The molecule has a planar...Ch. 9 - Practice Exercise 9.12 In the gas phase, beryllium...Ch. 9 - Practice Exercise 9.13
What kind of hybrid...Ch. 9 - What kind of hybrid orbitals are expected to be...Ch. 9 - Use the VSEPR model to predict the shape of the...Ch. 9 - What kind of orbitals arc used by Xe in the XeF4...Ch. 9 - Explain how to decide what kind of hybrid orbitals...Ch. 9 - If we assume that nitrogen uses sp3 hybrid...Ch. 9 - Practice Exercise 9.19
What is the shape of the ...Ch. 9 - Practice Exercise 9.20
Consider the molecule...Ch. 9 - Practice Exercise 9.21
Consider the molecule...Ch. 9 - The molecular orbital energy level diagram for the...Ch. 9 - The MO energy level diagram for the nitrogen...Ch. 9 - Practice Exercise 9.24
The nitrate ion, , has...Ch. 9 - Prob. 25PECh. 9 - Arrange the following elements in order of...Ch. 9 - Practice Exercise 9.27
What is the hybridization...Ch. 9 - Sketch the following molecular shapes and give the...Ch. 9 - Sketch the following molecular shapes and give the...Ch. 9 - 9.3 What is the underlying principle on which the...Ch. 9 - What is an electron domain? How are nonbonding and...Ch. 9 - 9.5 How many bonding domains and how many...Ch. 9 - Sketch the following molecular shapes and give the...Ch. 9 - What arrangements of domains around an atom are...Ch. 9 - Why is it useful to know the polarities of...Ch. 9 - Prob. 9RQCh. 9 - 9.10 Under what conditions will a molecule be...Ch. 9 - What condition must be met if a molecule having...Ch. 9 - Use a drawing to show why the SO2 molecule is...Ch. 9 - What is meant by orbital overlap?Ch. 9 - How is orbital overlap related to bond energy?Ch. 9 - Use sketches of orbitals to describe how VB theory...Ch. 9 - 9.16 Why do atoms usually use hybrid orbitals for...Ch. 9 - 9.17 Sketch figures that illustrate the...Ch. 9 - 9.18 Sketch figures that illustrate the...Ch. 9 - 9.19 Why do Period 2 elements never use hybrid...Ch. 9 - What relationship is there, if any, between Lewis...Ch. 9 - How can the VSEPR model be used to predict the...Ch. 9 - If the central oxygen in the water molecule did...Ch. 9 - Using orbital diagrams, describe how sp3...Ch. 9 - Sketch the way the orbitals overlap to form the...Ch. 9 - We explained the bond angles of 107inNH3 by using...Ch. 9 - Using sketches of orbitals and orbital diagrams,...Ch. 9 - What two basic shapes have hybridizations that...Ch. 9 - 9.28 The ammonia molecule, , can combine with a...Ch. 9 - 9.29 How does the geometry around B and O change...Ch. 9 - How do and bonds differ?Ch. 9 - Why can free rotation occur easily around a -bond...Ch. 9 - 9.32 Using sketches, describe the bonds and bond...Ch. 9 - Sketch the way the bonds form in acetylene, C2H2.Ch. 9 - How does VB theory treat the benzene molecule?...Ch. 9 - Why is the higher-energy MO in H2 called an...Ch. 9 - Below is an illustration showing two 3d. orbitals...Ch. 9 - 9.37 Will the combination of 3d. orbitals in...Ch. 9 - Explain why He2 does nor exist but H2 does.Ch. 9 - 9.39 How does MO theory account for the...Ch. 9 - 9.40 On the basis of MO theory, explain why ...Ch. 9 - 9.41 What relationship is there between bond order...Ch. 9 - Sketch the shapes of the 2p,and*2p,MOs.Ch. 9 - 9.43 What is the theoretical basis of both valence...Ch. 9 - What shortcomings of Lewis structures and VSEPR...Ch. 9 - What is the main difference in the way VB and MO...Ch. 9 - What is a delocalized MO? Explain, in terms of...Ch. 9 - 9.47 What effect does delocalization have on the...Ch. 9 - Prob. 48RQCh. 9 - Prob. 49RQCh. 9 - 9.50 What is required to form a conduction band?
Ch. 9 - Prob. 51RQCh. 9 - Prob. 52RQCh. 9 - In calcium, why cant electrical conduction take...Ch. 9 - 9.54 What are allotropes? How do they differ from...Ch. 9 - Why are the Period 2 elements able to form much...Ch. 9 - Even though the nonmetals of Periods 3, 4, and 5...Ch. 9 - Which of the nonmetals occur in nature in the form...Ch. 9 - 9.58 Describe the structure of diamond. What kind...Ch. 9 - Describe the structure of graphene. What kind of...Ch. 9 - How is the structure of graphite related to the...Ch. 9 - Prob. 61RQCh. 9 - 9.62 How is the structure of a carbon nanotube...Ch. 9 - 9.63 What is the molecular structure of silicon?...Ch. 9 - Make a sketch that describes the molecular...Ch. 9 - 9.65 What are the different allotropes of...Ch. 9 - 9.66 What are the P—P—P bond angles in the ...Ch. 9 - Prob. 67RQCh. 9 - 9.68 What is the molecular structure of black...Ch. 9 - What are the two allotropes of oxygen?Ch. 9 - Draw the Lewis structure for O3. Is the molecule...Ch. 9 - 9.71 What beneficial function does ozone serve in...Ch. 9 - What is the molecular structure of sulfur in its...Ch. 9 - 9.73 Predict the shapes of (a) , (b) , (c) , (d) ,...Ch. 9 - Predict the shapes of (a) SF3+, (b) GeF4, (c) ,...Ch. 9 - Predict the shapes of...Ch. 9 - Predict the shapes of (a) TeF4, (b) SbCl6, (c)...Ch. 9 - Predict the shapes of...Ch. 9 - 9.78 Predict the shapes of .
Ch. 9 - Which of the following has a shape described by...Ch. 9 - Which of the following has a shape described by...Ch. 9 - Ethene, also called ethylene, is a gas used to...Ch. 9 - Ethyne, more commonly called acetylene, is a gas...Ch. 9 - 9.83 Predict the bond angle for each of the...Ch. 9 - 9.84 Predict the bond angle for each of the...Ch. 9 - 9.85 Which of the following molecules would be...Ch. 9 - Which of the following molecules would he expected...Ch. 9 - Which of the following molecules or ions would be...Ch. 9 - Which of the following molecules or ions would be...Ch. 9 - 9.89 Explain why is nonpolar, but is polar.
Ch. 9 - 9.90 Explain why is polar, but is not.
Ch. 9 - Use sketches of orbitals to show how VB theory...Ch. 9 - Hydrogen selenide is one of nature's most...Ch. 9 - Use orbital diagrams to explain how the beryllium...Ch. 9 - Use orbital diagrams to describe the bonding in...Ch. 9 - 9.95 Use orbital diagrams to describe the bonding...Ch. 9 - Describe the bonding in tellurium hexafluoride, a...Ch. 9 - Draw Lewis structures for the following and use...Ch. 9 - Draw Lewis structures for the following and use...Ch. 9 - Use the VSEPR model to help you describe the...Ch. 9 - Use the VSEPR model to help you describe the...Ch. 9 - 9.101 Use orbital diagrams to show that the...Ch. 9 - What kind of hybrid orbitals are used by tin in...Ch. 9 - A nitrogen atom can undergo sp2 hybridization when...Ch. 9 - A nitrogen atom can undergo sp hybridization and...Ch. 9 - Tetrachloroethylene, a common dry-cleaning...Ch. 9 - 9.106 Phosgene, , was used as a war gas during...Ch. 9 - 9.107 What kind of hybrid orbitals do the numbered...Ch. 9 - What kind of hybrid orbitals do the numbered atoms...Ch. 9 - 9.109 What kinds of bonds are found in the...Ch. 9 - 9.110 What kinds of bondsare found in the numbered...Ch. 9 - Construct the molecular orbital diagram for O2....Ch. 9 - Construct the molecular orbital diagram for N2....Ch. 9 - Use the MO energy diagram to predict (a) the bond...Ch. 9 - Use the MO energy diagram to predict (a) the bond...Ch. 9 - Assume that in the NO molecule the molecular...Ch. 9 - 9.116 Assume that in the NO molecule the molecular...Ch. 9 - Which of the following molecules or ions are...Ch. 9 - 9.118 Which of the following molecules or ions are...Ch. 9 - *9.119 Construct the MO energy level diagram for...Ch. 9 - If boron and nitrogen were to form a molecule with...Ch. 9 - 9.121 Formaldehyde has the Lewis structure
What...Ch. 9 - Prob. 122RQCh. 9 - Antimony forms a compound with hydrogen that is...Ch. 9 - Describe the changes in molecular geometry and...Ch. 9 - Prob. 125RQCh. 9 - Prob. 126RQCh. 9 - Phosphorus trifluoride, PF3, has FPF bond angles...Ch. 9 - A six-membered ring of carbons can hold a double...Ch. 9 - The more electronegative are the atoms bonded to...Ch. 9 - Alone pair of electrons in the valence shell of an...Ch. 9 - *9.131 The two electron pairs in a double bond...Ch. 9 - In a certain molecule, ap orbital overlaps with a...Ch. 9 - *9.133 If we assign the internuclear axis in a...Ch. 9 - The peroxynitrite ion, OONO-, is a potent toxin...Ch. 9 - *9.135 An ammonia molecule, , is very polar,...Ch. 9 - There exists a hydrocarbon called butadiene, which...Ch. 9 - Prob. 137RQCh. 9 - 9.138 Five basic molecular shapes were described...Ch. 9 - 9.139 Compare and contrast the concepts of...Ch. 9 - Why doesnt a carbon-carbon quadruple bond exist?Ch. 9 - What might the structure of the iodine...Ch. 9 - The FF bond in F2 is weaker than the ClCl bond in...Ch. 9 - Molecular orbital theory predicts the existence of...Ch. 9 - The structure of the diborane molecule, B2H6, is...
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- Use the VSEPR model to predict the bond angles around each central atom in the following Lewis structures (benzene rings are frequently pictured as hexagons, without the letter for the carbon atom at each vertex). Note that the drawings do not necessarily depict the bond angles correctly.arrow_forward• explain the formation of multiple bonds in terms of the overlap of a combination of hybridized and unhybridized atomic orbitals.arrow_forwardDescribe the shapes of C2H6 and C2H4. In doing so, explain why one molecule is planar and why the other molecule cannot be planar.arrow_forward
- 9) HCCCO₂H, is an organic hydrocarbon. a) Draw a geometrically accurate structure so that the formal charge of each atom is zero identifying the bond angles (Draw it BIG!). b) Identify the hybridization about each atom (not H) forming a bond c) How many o or π bonds are there in this molecule d) The combustion of the hydrocarbon produces carbon dioxide and water in the gaseous state. Use average bond enthalpies to determine enthalpy of reactionarrow_forwarddescribe the hybridization, bonding and geometry in a molecule of benzene. Explain the stability in terms of two resonance structures.arrow_forwardDescribe the concept of hybridization with examples of ethane, ethylene, and acetylene moleculesarrow_forward
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