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Chapter 7: Molecular Structures 371
Chapter 7: Molecular Structures

Teaching for Conceptual Understanding
Introduce this chapter by explaining the importance of understanding molecular shapes. Good examples include the
structure of DNA, designer drugs, and physical properties of molecules. If you (or a colleague) use molecular
modeling in your research, tell your students about the work and show them examples.
Understanding covalent bonding and an ability to draw correct Lewis structures are both prerequisites for
understanding and predicting correct molecular geometries. As necessary, the students should be told to review
Chapter 6.
Electron-region geometry and molecular geometry can be confusing for students. Use balloon models (Figure 7.3)
to illustrate the differences and similarities between the two. For example ammonia has a tetrahedral electron-region
geometry and a triangular pyramidal molecular geometry. Construct a four-balloon model from three balloons of
the same color and one of a different color. Explain the four balloons represent the regions in which electron pairs
are located. The same colored balloons are bonding regions and the different colored balloon the lone pair region.
Although a lone pair of electrons contributes to the arrangement of the atoms in the molecule, it is not part of the
chemical formula or structure and can be removed from view. Pop the different colored balloon and have the
students focus on the three remaining balloons (it is important you continue holding the three balloons in a triangular
pyramidal arrangement). A similar example explains the structure of water.
Hydrogen bonding is a concept for which there are many student misconceptions, the most obvious being it is a
bonding between two hydrogen atoms or two hydrogen molecules. Another is that hydrogen bonding occurs only
between two like molecules. Questions for Review and Thought 94-95 assess student understanding of hydrogen
bonding. If you are teaching students whose majors involve the study of living systems, it is very important that
they have a solid understanding of the concept. Take the time to teach and test it well.
Suggestions for Effective Learning

Models are an absolute necessity for teaching molecular geometry. Ball-and-stick models will work best to clearly
illustrate the different structures and they will correspond to the drawings in the textbook. Balloon models, as
described above, work well when explaining regions of bonding and lone-pair electrons.
If you draw three-dimensional structures in a two-dimensional plane, use the solid (—), dashed line (- - - -), and
wedge ( ) notation explained in Section 7-1. This notation is used throughout the textbook and in other
(organic, biochemistry, biology) textbooks.
Tell students that Tables 7.1-7-3 are good summaries of molecular geometry types.
Students sometimes confuse the terms “intermolecular” and “intramolecular.” It is sometimes useful to relate the
prefixes inter-and intra- to the familiar terms “intercollegiate” sports and “intramural” sports.
Demonstrating with bar magnets is a simple way to illustrate dipole-dipole attractions.
A very good example of enantiomers is (+)- and (–)-carvone, (–)-carvone smells like spearmint and (+)-carvone
smells like caraway. Show students the different structures and bring samples of each to class for them to smell. A
good question to ask is: Do you think your nose sensors are chiral?
If you discuss spectroscopy and the bending, stretching vibrating, rotating, and translating nature of bonds and
molecules, physically illustrate each (by bending your arms in and out of sync, turning around, etc). Your students
will grasp the concept quickly and probably remember it for years to come.
Cooperative Learning Activities

Questions, problems, and topics that can be used for Cooperative Learning Exercises and other group work are:
• Questions for Review and Thought in this chapter: 62, 72, 79, 80, 85, 86, 87, 88, 96, 109, and 110
• Conceptual Challenge Problems: CP7.A
372 Chapter 7: Molecular Structures
End-of-Chapter Solutions for Chapter 7

Summary Problem
Part I
Result: (a) See structure below; tetrahedral, angular, 109.5°, sp3 (b) Triangular planar, triangular planar,
120°, sp2 (c) See structure below; triangular planar, triangular planar, 120°, sp2 (d) See structure below;
linear, linear, 180°, sp (e) See structure below; tetrahedral, triangular pyramidal, 109.5°, sp3
Analyze: Write Lewis structures for a list of formulas and identify their electron geometry, the shape, and the
hybridization of the central atom.
Plan: Follow the plan in the solution to Question 6.15 for writing Lewis structures, then determine the number of
bonded atoms and lone pairs on the central atom, determine the designated type (AXnEm), and use Tables 7.1-7.3.
Use the electron geometry to determine the number of electron pairs around the central atom. Select a hybridization
that accommodates the appropriate number of bonds as described in Section 7-2.
Execute:
(a) BrF2+ (20 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the molecular
geometry is angular. The bond angle is slightly less than 109.5°. The Br atom must
be sp3-hybridized to accommodate the two bonds and two lone pairs.
(b) OCCl2 (24 e–) The type is AX3E0, so the electron-region geometry and the molecular geometry are
triangular planar. The bond angles are 120°. The C atom must be sp2-hybridized to
accommodate the three bonded atoms.
(c) CH3+ (6 e–) The type is AX3E0, so the electron-region geometry and the molecular geometry are
triangular planar. The bond angles are 120°. The C atom must be sp2-hybridized to
accommodate the three bonds.
(d) SeCS (16 e–) The type is AX2E0, so the electron-region geometry and the molecular geometry are
linear. The bond angle is 180°. The C atom must be sp-hybridized to accommodate
the two bonded atoms.
(e) CH3– (8 e–) The type is AX3E1, so the electron-region geometry is tetrahedral and the molecular
geometry is triangular pyramidal. The bond angle is slightly less than 109.5°. The C
atom must be sp3-hybridized to accommodate the three bonds and one lone pair.
Part II
Result: (a) C14H18O5N2 (b) sp3 (c) sp3 (d) sp3 (e) sp2 (f) See structure below
Analyze, Plan, and Execute:

(a) To get the formula, count the number of each type of atom. There are six carbon atoms and five hydrogen
atoms in the benzene ring.
The formula is C14H18O5N2.
(b) There are twelve atoms that have triangular planar molecular geometry. Nine atoms have three bonded atoms
and no lone pairs for type AX3E0. Three O atoms have one bonded atom and two lone pairs for type AXE2.
All eleven are circled below. Any three of these will answer the question.
(c) There are five C atoms that have tetrahedral molecular geometry, with four bonded atoms and no lone pairs for
type AX4E0. All five are circled below. Any three of these will answer the question.
(d) Two O atoms have bent (angular) molecular geometry, with two bonded atoms and two lone pairs for type
AX2E2. They are circled, here:
(e) and are both AX3E1, so the electron-region geometry is tetrahedral.
The three bonds and one lone pair need sp3-hybridization on the N atoms.
(f) Both CH2 groups: are AX4E0, so the electron-region geometry is tetrahedral.
The four bonds need sp3-hybridization on the C atoms.
(g) Both carbon atoms in the C=O groups: and are AX3E0, so the electron-region
geometry is tetrahedral. The two bonds and two lone pairs need sp3-hybridization on the O atoms.
(h) The oxygen atom to which a methyl (–CH3 ) group is attached: is AX2E2, so the electron-region
geometry is triangular planar. The three bonds need sp2-hybridization on the C atoms.
(i) All single bonds are sigma (σ) bonds. All double bonds are composed of one sigma (σ) bond and one pi (π)
bond. The diagram below identifies sigma (σ) and pi (π) bonds involving C atoms and N atoms:
H O H O H
H σ π σ σ π σ σ
σ
σ σ σ σ σ σ σ
N C C N C C O C σ H
σ σ
H σ σ σ
σ σ σ σ
H C H H H C H H
σ σ
π
O H H C H
σ C σ O σ σ σ
σ
C π C
σ π σ
C π C σ
σ σ
H σ C H
σ
H
Part III
Result: See structure below
Analyze, Plan, and Execute: The structure of water and the highly polar bonds provide excellent conditions for
forming hydrogen bonds.
Because glucose also contains –OH groups and a C=O group, there is ample opportunity for the glucose atoms
(shown in bold) to interact with water molecules using hydrogen bonding (show as dashed lines: (- - - -). The
H atoms in water are attracted to O atoms in glucose and the O atom in water is attracted to the H atoms in glucose,
when they are bonded to O atoms. Notice: hydrogen bonding will not occur between O atoms in water and the
H atoms bonded to C atoms.
H H
O
O H
H
H
H O H H H H H
O
O O
H C C C C C C O
H
H
H H
O H O O H O
H H H
H H H H H
O H O
O
H O H O O H H
H
H H
Questions for Review and Thought

Review Questions
1. Result/Explanation: The physical basis of the VSEPR (Valence-Shell Electron-Pair Repulsion) model is the
repulsion of like charges. Because electron pairs will repel each other, they will arrange themselves to be as far
from each other as possible. This model is used to predict the shape of molecules and ions by describing the
relative orientation of atoms connected to each other with covalent bonds.
2. Result/Explanation: Electron-region geometry identifies the positions of all the electron regions (usually pairs)
around the central atom. The molecular geometry identifies the positions of all the atoms bonded to the central
atom. For example, look at H2O:
The central O atom in H2O has four electron pairs, two bonding pairs and two lone pairs, so its electron-region
geometry is tetrahedral. The two atoms bonded to the O in the AX2E2 type are arranged with an angular
molecular geometry.
3. Result/Explanation: Use Table 7.1
Number of electron pairs Electron-region geometry
2 linear
3 triangular planar
4 tetrahedral
5 triangular bipyramidal
6 octahedral
4. Result/Explanation: Use Tables 7.1-7.3
(a) Two atoms bonded together must be linear.
(b) AX2E2 type has angular (bent) molecular geometry.
(c) AX3E1 type has triangular pyramidal molecular geometry.

(d) AX4E0 type has tetrahedral molecular geometry.
AX2E2, AX3E1, and AX4E0 types all have a tetrahedral estimated H–A–H bond angle of 109.5°.
5. Result/Explanation: To have a triangular planar molecule with three electron regions around the central atom,
the central atom must have three bonded atoms and no lone pairs. To have an angular molecule with three
electron pairs around the central atom, the central atom must have two bonded atoms and one lone pair. In the
first case, the bond angles are predicted to be 120°. In the second case, they are 109.5°.
6. Result/Explanation: Following the example at the end of Section 7-2e, we’ll look at each atom in the molecule
with more than one atom bonded to it and determine the electron-region geometry at that center, then determine
the shape of the molecule from the collective geometries at these centers.
Problem-Solving Example 7.6 gives the formula for ethylene as C2H4. The Lewis structure for C2H4 looks like
this:
H H
C C
H H
Looking at the first C atom, it has three bonded atoms (two H atoms and one C atom) and no lone pairs. That
gives it three electron-regions and makes it an AX3E0 type, so the atoms bonded to the first C atom are arranged
with a triangular planar geometry. Looking at the second C atom, it also has three bonded atoms and no lone
pairs, so it is also AX3E0 type and the atoms bonded to that C atom are arranged with a triangular planar
geometry. VESPR alone does not assure us that these two planes are coplanar, but the π bond representing the
second bond in the double bond would not be formed unless they are. With all the atoms in a common plane,
the molecule is planar.
7. Result/Explanation: A molecule with polar bonds can be nonpolar if the bond poles are equal and point in
opposite directions. CO2 is a good example of a nonpolar molecule with polar bonds.
.. ..
O
.. C O
..
8. Result/Explanation: In Section 7-7b, we learn that Erwin Chargaff measured the quantities of nitrogen bases in
DNA. He learned every organism has a characteristic base composition in all cells and those bases occur in
pairs: adenine with thymine and guanine with cytosine.
9. Result/Explanation: In Section 7-7a, we learn that the deoxyribose units in the backbone chain are joined
through phosphate diester linkages. The margin note describes the creation of the phosphate diester. The
phosphate units join nucleotides into a polynucleotide chain that has a backbone of alternating deoxyribose and
phosphate units in a long strand with the various nitrogenous bases extending out from the sugar-phosphate
backbone. A DNA segment with nucleotides bonded together is shown in Figure 7.24.
10. Result/Explanation: Infrared spectroscopy is used to characterize the structure of molecules. The infrared
spectrum shows the specific frequencies absorbed when the molecule undergoes specific types of motions.
Each molecule, with its unique arrangement of atoms and bonds, interacts differently with infrared light; hence,
the resulting spectrum is also unique, much like the individual fingerprints of people.
11. Result/Explanation: For infrared radiation to be absorbed, the motion of the molecule to have a frequency in
the range of 1012 - 1014 s–1.
Topical Questions
Molecular Shape (Section 7-2)
12. Result/Explanation: Section 7-1 shows all and stick models, space filling models, and two-dimensional pictures
using wedges and dashed lines:
(a)
(b)
(c)
13. Result: See structures below; (a) linear (b) triangular planar (c) octahedral (d) triangular
pyramidal
Analysis: Write Lewis structures for a list of chemical formulas and identify their shape.
Plan: Follow the systematic plan for Lewis structures given in the solution to Question 6.15, then determine the
number of bonded atoms and lone pairs on the central atom, determine the designated type (AXnEm) and use
Table 7.1. Notice: It is not necessary to take the time to expand the octet of a central atom solely for the
purposes of lowering its formal charge, because the shape of the molecule will not change. Hence, most Lewis
structures here are written to follow the octet rule, unless the atom must have more than eight electrons for
another reason.
Execute:
(a) BeH2 (4 e–) The type is AX2E0, so it is linear.
(b) CH2Cl2 (20 e–) The type is AX4E0, so it is tetrahedral.
(c) BH3 (6 e–) The type is AX3E0, so it is triangular planar.
(d) SeCl6 (48 e–) The type is AX6E0, so it is octahedral.
(e) PF3 (26 e–) The type is AX3E1, so it is triangular pyramidal.

14. Result: See structures below; (a) tetrahedral, triangular pyramidal (b) tetrahedral, angular (109.5°)
(c) linear, linear (d) tetrahedral, angular (109.5°)
Analysis: Write Lewis structures for a list of chemical formulas and identify their shape.
Tables 7.1, 7.2, or 7.3.
Execute:
(a) NH2Cl (14 e–) The type is AX3E1, so the electron-region geometry is tetrahedral and the
molecular geometry is triangular pyramidal.
(b) OF2 (20 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the
molecular geometry is angular (109.5°).
(c) SCN– (16 e–) The type is AX2E0, so the electron-region geometry and the molecular geometry
are both linear.
(d) HOF (14 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the
15. Result: See structures below; (a) triangular planar, triangular planar (b) triangular planar, triangular
planar (c) tetrahedral, triangular pyramidal (d) tetrahedral, triangular pyramidal
Analysis: Write Lewis structures for a list of chemical formulas and identify their electron-region geometry and
the molecular geometry.
Tables 7.1, 7.2, or 7.3.
Execute:
(a) BO33– (24 e–) The type is AX3E0, so both the electron-region geometry and the molecular
geometry are triangular planar.
(b) CO32– (24 e–) AX3E0, so both the electron-region geometry and the molecular geometry are
triangular planar.
(c) SO32– (26 e–) AX3E1, so the electron-region geometry is tetrahedral and the
molecular geometry is triangular pyramidal.
–
(d) ClO3 (26 e–) AX3E1, so the electron-region geometry is tetrahedral and the molecular
geometry is triangular pyramidal.
All of these ions and molecules have one central atom with three O atoms bonded to it. The number and type of
bonded atoms is constant. The geometries vary depending on how many lone pairs are on the central atom.
The structures with the same number of valance electrons all have the same geometry.
16. Result: See structures below; (a) linear, linear (b) triangular planar, angular (120°) (c) triangular
planar, angular (120°) (d) triangular planar, angular (120°) (e) tetrahedral; angular (109.5°); See
comment below
Plan: Adapt the method given in the solution to Question 15.
Execute:
(a) CO2 (16 e–) The type is AX2E0, so the electron-region geometry and the molecular geometry
are both linear.
–
(b) NO2 (18 e–) The type is AX2E1, so the electron-region geometry is triangular planar and the
molecular geometry is angular (120°).
(c) SO2 (18 e–) The type is AX2E1, so the electron-region geometry is triangular planar and the
(d) O3 (18 e–) The type is AX2E1, so the electron-region geometry is triangular planar and the
(e) ClO2– (20 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the
Comment: All of these ions and molecules have one central atom with two O atoms bonded to it. The number
and type of bonded atoms is constant. The geometries vary depending on how many lone pairs are on the
central atom. The structures with the same number of valance electrons all have the same geometry.
17. Result: See structures below; XeOF2: triangular bipyramidal, T-shaped; ClOF3: triangular bipyramidal,
seesaw; their molecular geometries are different.
Execute:
XeOF2 (28 e–) The type is AX3E2, so the electron-region geometry is triangular bipyramidal
and the molecular geometry is T-shaped.
ClOF3 (34 e–) The type is AX4E1, so the electron-region geometry is triangular bipyramidal
and the molecular geometry is seesaw.
The two molecules have the same electron-region geometry, but their molecular geometries are different.
18. Result: HCP: linear, linear; I3+: tetrahedral, angular; their charge, type, electron-region geometry, and
molecular geometries are all different.
Execute:
HCP (10 e–) The type is AX2E0, so the electron-region geometry and the molecular geometry
is linear.
I3+ (20 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the
molecular geometry is angular (bent).
The two species have the same number of atoms, but their charge, type, electron-region geometry, and
molecular geometries are all different.
19. Result: See structures below; (a) octahedral, octahedral (b) triangular bipyramid; seesaw (c) triangular
bipyramidal; triangular bipyramidal (d) octahedral; square planar
Execute:
(a) SiF62– (48 e–) The type is AX6E0, so both the electron-region geometry and the molecular
geometry are octahedral.
(b) SF4 (34 e–) The type is AX4E1, so the electron-region geometry is triangular bipyramid and
the molecular geometry is seesaw.
(c) PF5 (40 e–) The type is AX5E0, so the electron-region geometry is triangular bipyramidal and
the molecular geometry is triangular bipyramidal.
(d) XeF4 (36 e–) The type is AX4E2, so the electron-region geometry is octahedral and the
molecular geometry is square planar.
20. Result: See structures below; (a) triangular bipyramid; linear (b) triangular bipyramid; T-shaped
(c) octahedral; square planar (d) octahedral; square pyramidal
Execute:
–
(a) ClF2 (22 e–) The type is AX2E3, so the electron-region geometry is triangular bipyramid and
the molecular geometry is linear.
(b) ClF3 (28 e–) The type is AX3E2, so the electron-region geometry is triangular
bipyramid and the molecular geometry is T-shaped.
(c) ClF4– (36 e–) The type is AX4E2, so the electron-region geometry is octahedral and the
molecular geometry is square planar.
(d) ClF5 (42 e–) The type is AX5E1, so the electron-region geometry is octahedral and the
molecular geometry is square pyramidal.
–
21. Result: I3+ has AX2E2 with angular geometry; I3 has AX2E3 with linear geometry.
Analysis: Explain why one ion is bent and one is not.

Execute:
I3+ (20 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the
molecular geometry is angular (bent).
–
I3 (22 e–) The type is AX2E3, so the electron-region geometry is trigonal bipyramidal
and the molecular geometry is linear.
The anion has two more electrons than the cation. The extra pair of electrons join the first two lone pairs on the
central atom, changing the electron-region geometry and forcing the bond pairs to a linear orientation.
22. Result: (a) O–S–O angle is 120° (b) F–B–F angle is 120° (d) H–C–H angle is 120°; C–C–N angle is
180° (c) N–O–H angle is 109.5°; O–N–O is 120°
Analysis: Given chemical formulas and some structural information, predict some approximate bond angles.
Plan: We will adapt the method given in the solution to Question 15 to get the electron-region geometry of the
second atom in the bond description (e.g., A in X–A–Y). We use this to predict the approximate bond angle.
Execute:
(a) SO2 (18 e–) The type is AX2E1, so the electron-region geometry is triangular planar and
the approximate O–S–O angle is 120°.
(b) BF3 (24 e–) The type is AX3E0, so the electron-region geometry is triangular planar and
the approximate F–B–F angle is 120°.
(c) CH2CHCN (20 e–) Look at the first C atom: The type is AX3E0, so the electron-region
geometry is triangular planar and the approximate H–C–H angle is 120°.
Look at the third C atom: The type is AX2E0, so the electron-region
geometry is linear and the approximate C–C–N angle is 180°.
(d) HNO3 (24 e–) Look at the first O atom: The type is AX2E2, so the electron-region
geometry is tetrahedral and the approximate N–O–H angle is 109.5°.
Look at the N atom: The type is AX3E0, so the electron-region geometry
is triangular planar and the approximate O–N–O angle is 120°.
23. Result: (a) Cl–S–Cl angle is 109.5° (b) N–N–O angle is 180°
(c) O–C–N angle is 120°; H–N–H angle is 109.5° (d) H–C–O angle is 109.5°; C–O–H angle is 109.5°
Plan: We adapt the method given in the solution to Question 22.
Execute:
(a) SCl2 (20 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the
approximate Cl–S–Cl angle is 109.5°.
(b) N2O (16 e–) The type is AX2E0, so the electron-region geometry is linear and the
approximate N–N–O angle is 180°.
(c) NH2CONH2 (24 e–) Look at the C atom: The type is AX3E0, so the electron-region geometry is
triangular planar and the approximate O–C–N angle is 120°.
Look at the second N atom: The type is AX3E1, so the electron-region geometry
is tetrahedral and the approximate H–N–H angle is 109.5°.
(d) CH3OH (14 e–) Look at the C atom: The type is AX4E0, so the electron-region geometry is
tetrahedral and the approximate H–C–O angle is 109.5°.
Look at the O atom: The type is AX2E2, so the electron-region geometry is
tetrahedral and the approximate C–O–H angle is 109.5°.
24. Result: (a) four at 90°, one at 120°, and one at 180° (b) 90° and 120° (c) eight at 90° and two at 180°
Execute:
(a) SeF4 (34 e–) The type is AX4E1, so the electron-region geometry is triangular bipyramid.
The Fequitorial–Se–Fequitorial angle is 120°, the Fequitorial–Se–Faxial angles are
90° and Faxial–Se–Faxial angle is 180°.
(b) SOF4 (40 e–) The type is AX5E0, so the electron-region geometry is triangular
bipyramidal, equatorial-F–S–O angles are 120° and the axial-F–S–O angles
are 90°.
(c) BrF5 (42 e–) The type is AX5E1, so the electron-region geometry is octahedral and all the
F–Br–F angles are 90°. The angles across the bottom of the structure will
be 180°.
25. Result: (a) Twelve at 90° (b) 180° (c) 180°

Analysis: Given chemical formulas, predict some approximate bond angles.
Execute:
(a) SF6 (48 e–) The type is AX6E0, so the electron-region geometry is octahedral and all 12
of the F–S–F angles are 90°.
(b) XeF2 (22 e–) The type is AX2E3, so the electron-region geometry is triangular
bipyramidal, and the F–Xe–F angle is 180°.
(c) ClF2– (22 e–) The type is AX2E3, so the electron-region geometry is triangular
bipyramidal, and the F–Cl–F angle is 180°.
26. Result: NO2+
Analysis: Given two chemical formulas, predict which has a greater O–N–O bond angle.
Execute:
NO2 molecule and NO2+ ion differ by only one electron. NO2 has 17 electrons and NO2+ has 16 electrons.
Their Lewis structures are quite similar:
Using VESPR, NO2 is triangular planar (AX2E1) and NO2+ is linear (AX2). The predict O–N–O angle in NO2
is approximately 120°. The predict O–N–O angle in NO2+ ion is 180°. So, NO2+ has a greater O–N–O angle.
– –
27. Result: ClF2 ; VSEPR predicted angle for ClF2 is 180° (AX2E3) and for ClF2+ is 109.5° (AX2E2).
Analysis: Given two chemical formulas, explain which has a greater O–N–O bond angle.
Execute:
ClF2+ cation and ClF2– anion differ by two electrons. ClF2+ has 20 electrons and ClF2– has 22 electrons.
ClF2+ cation has type AX2E2. The electron-region geometry is tetrahedral, and the F–Cl–F angle is 109.5°:
ClF2– anion has type AX2E3. The electron-region geometry is triangular bipyramidal, and the F–Cl–F angle is
180°.
According to the VESPR model, we predict that the F–Cl–F angle in a ClF2– anion is a greater angle than the
angle in a ClF2+ cation.
Chirality in Organic Compounds (Section 7-2)

28. Result: See circles on structures below
Analysis: Given structural formulas, identify the chiral centers.
Plan: Chiral centers are C atoms with four bonds, where each fragment bonded is different. Cirle the chiral
centers.
Execute:
(a) The second and third C atoms have four different fragments: HOOC–, HO–, –H, and –CH(OH)COOH.
O HO HO O
HO C C C C H
H H
(b) This molecule has no chiral centers. The two inner C atoms do not have four bonds. The first C atom has
three H atoms bonded.
O O
CH3 C C OH
(c) The third C atom has four different fragments: CH3CH2–, –H, –COOH, and –NH2. The first and second C
atoms have three and two H atoms bonded, respectively, so they are not chiral centers.
H O
CH3 CH2 C C OH
NH2
Plan: We will follow the plan from Question 28.
Execute:
(a) The second C atom has four different fragments: CH3–, HO–, –CH2OH, and –H. The first C atom has
three H atoms bonded and the third C atom has two H atoms bonded, so they are not chiral centers.
HO OH
CH3 C C H
H H
(b) This molecule has no chiral centers. The first two C atoms do not have four bonds. The third C atom has
two H atoms bonded.
H C C CH2 OH
H H
(c) The third C atom has four different fragments: CH3CCl2–, F–, –Cl, and –H. The first C atom has two H
atoms bonded. The second C atom has two Cl atoms bonded, so they are not chiral centers.
Cl F
CH3 C C Cl
Cl H
30. Result: See circle on structure below
Plan: We will adapt the plan from the solution to Question 28.
Execute:
(a) This molecule has no chiral centers. The end C atoms have three H atoms bonded, and the second C atom
has three CH3 fragments.
H Cl H
H C C C H
H CH3 H
(b) This molecule has no chiral centers. The end C atoms have two or three H atoms bonded, and the second C
atom has two CH3 fragments.
H H H
Cl C C C H
H CH3 H
(c) The second C atom has four different fragments: CH3–, Br–, –CH2CH2CH3, and –H. The other C atoms
have more than one H atom bonded, so they are not chiral centers.
H Br H H H
H C C C C C H
H H H H H
(d) This molecule has no chiral centers. Most of the C atoms have two or three H atoms, and the second C
atom has two –CH2CH3 fragments.
H H Br H H
H C C C C C H
H H H H H
Plan: We will adapt the plan from the solution to Question 28.
Execute:
(a) The second C atom has four different fragments: CH3–, Br–, –CH2CH3, and –Cl. The other C atoms have
more than one H atoms bonded, so they are not chiral centers.
H Br H H
H C C C C H
H H H H
(b) This molecule has no chiral centers. The end C atoms have three H atoms bonded, and the third C atom has
three –CH3 fragments.
H CH3 H
H C C C H
H H H
(c) The fourth C atom has four different fragments: CH3CH=CH–, H–, –CH3, and –Br. The end C atoms have
three H atoms bonded, and the second and third C atoms have only three bonds, so they are not chiral
centers.
H H H H H
H C C C C C H
H Br H
Hybridization (Section 7-3, 7-4)

32. Result: tetrahedral, sp3-hybridization
Analyze and Plan: Write a Lewis structure for CHCl3 and use VSEPR to determine the molecular geometry as
described in the solution to Question 15. Use the chart in Section 7-3c to determine the hybridization of the
central atom using the electron-region geometry.
Execute: The molecule is AX4E0 type, so its electron-region geometry and its molecular geometry are
tetrahedral.
To make four equal bonds with an electron-region geometry of tetrahedral, the C atom must be sp3-hybridized.
33. Result: Both C atoms are tetrahedral centers with four bonds and the O atom is bent at 109.5° with two
bonds and two lone pairs; all four atoms have sp3-hybridization
Analyze: Describe the geometry and hybridization of several atoms in a structural formula.
Plan and Execute: Write a Lewis structure for HOCH2CH2OH and use VSEPR as described in the solution to
Question 15 to determine the geometry of each of the C and O atoms. Use the chart in Section 7-3c to
determine the hybridization of each atom using the electron-region geometry.
The O atoms are AX2E2 type, so the H–O–C angles will be approximately the tetrahedral angle of 109.5°.
The C atoms are AX4E0 type, so the O–C–C, O–C–H, H–C–C and H–C–H angles will also be approximately
the tetrahedral angle of 109.5°.
The O atoms must be sp3-hybridized to make two bonds and two lone pairs with an electron-region geometry
of tetrahedral. The C atoms must be sp3-hybridized to make four bonds with an electron-region geometry of
tetrahedral.
34. Result: The central S atom in SCl2 has sp3 hybridization; the central C atom in OCS is sp-hybridized.
SCl2 has two single bonds. OCS has two double bonds.
Analyze: Describe the geometry and hybridization of several atoms in a structural formula.
Plan and Execute: Follow the procedure described in the solution to Question 32.
SCl2 (20 e–) The type is AX2E2, so the electron-region geometry is tetrahedral and the
molecular geometry is bent (109.5°).
The S atom must be sp3-hybridized.

OCS (16 e–) The C atom must be the central atom. The type is AX2E0, so the electron-
region geometry is linear and the O–C–S angle is 180°.
The C atom must be sp-hybridized.

The bonding in these molecules is polar covalent. The two bonds in SCl2 are single bonds. The two bonds in
OCS are double bonds.
35. Result: (a) methyl carbon: sp3 carboxyl carbon: sp2 (b) methyl carbon: 109.5°, carboxyl carbon: 120°
Analyze: Given a structural formula, describe the geometry and hybridization of several atoms and determine
the approximate bond angle.
Plan and Execute: Draw the Lewis structure and use VSEPR to determine the electron-region geometry of each
of the C atoms as described in the solution to Question 15. The bond angles and hybridization are associated
with the electron-region geometry using Figures 7.1 and 7.2 and the chart in Section 7-3c.
(a) Look at the left C atom: The type is AX4E0, so the electron-region geometry is tetrahedral and this C
atom’s hybridization is sp3. Look at the right C atom: The type is AX3E0, so the electron-region geometry
is triangular planar and this C atom’s hybridization is sp2.
(b) The sp3-hybridized C atom has tetrahedral H–C–H and H–C–C bond angles of approximately 109.5°. The
sp2-hybridized C atom has triangular planar C–C–O and O–C–O bond angles of approximately 120°.
36. Result: (a) ammonium N: sp3, nitrate N: sp2 (b)ammonium N: 109.5°, nitrate N: 120°
Analyze: Given a structural formula, describe the geometry and hybridization of several atoms and determine
the approximate bond angle.
Plan and Execute: Adapt the plan described in the solution to Question 35.
(a) Look at the first N atom: The type is AX4E0, so the electron-region geometry is tetrahedral and this N
atom’s hybridization is sp3. Look at the second N atom: The type is AX3E0, so the electron-region
geometry is triangular planar and this N atom’s hybridization is sp2.
(b) The sp3-hybridized N atom has tetrahedral H–N–H bond angles of approximately 109.5°. The sp2-
hybridized N atom has triangular planar O–N–O bond angles of approximately 120°.
37. Result: N: sp3, 109.5°; first two C atoms (from left to right): sp3, 109.5°; third C: sp2, 120°;
top O: sp2; right O: sp3, 109.5°. The shortest carbon-to-oxygen bond is C=O.
Analyze: Given a structural formula, describe the geometry and hybridization of several atoms, determine the
approximate bond angles, and identify the shortest CO bond.
Plan and Execute: Adapt the plan described in the solution to Question 35. Consult Section 6-6c for assistance
in determining the shortest carbon-to-oxygen bond.
For convenient reference, some atoms are numbered below from left to right: C1, C2, C3, O1, and O2.
Look at C1: The type is AX4E0, so the electron-region geometry is tetrahedral, its hybridization is sp3, and has
bond angles are approximately 109.5°.
Look at C2: The type is AX4E0, so the electron-region geometry is tetrahedral, its hybridization is sp3, and the
bond angles are approximately 109.5°.
Look at the N atom: The type is AX3E1, so the electron-region geometry is tetrahedral, its hybridization is sp3,
and the bond angles are approximately 109.5°.
Look at C3: The type is AX3E0, so the electron-region geometry is triangular planar, its hybridization is sp2, and
the bond angles are approximately 120°.
Look at the N atom: The type is AX3E1, so the electron-region geometry is tetrahedral, its hybridization is sp3,
and the bond angles are approximately 109.5°.
Look at O1: The type is AX1E2, so the electron-region geometry is triangular planar, its hybridization is sp2.
This oxygen has only one bond to carbon, so there are no associated bond angles.
Look at O2: The type is AX2E2, so the electron-region geometry is tetrahedral, its hybridization is sp3, and the
bond angle is approximately 109.5°.
The shortest carbon-to-oxygen bond is the double bond, C3=O1. This molecule does have a resonance structure
with the double bond on O2, but that structure has non-zero formal charges, so it contributes little to the
resonance hybrid.
38. Result: (a) first two C atoms (with single bonds): sp3, 109.5°; third and fourth C’s (with a triple bond):
sp, 180° (b) shortest: C≡C (c) strongest: C≡C
Analyze: Given a structural formula, describe the geometry and hybridization of several atoms, determine the
approximate bond angles, and identify the shortest CC bond.
Plan and Execute: Adapt the plan described in the solution to Question 37.
For convenient reference, some atoms are numbered below from left to right: C1, C2, C3, and C4.
(a) Look at C1: The type is AX4E0, so the electron-region geometry is tetrahedral, its hybridization is sp3, and
has bond angles are approximately 109.5°.
Look at C2: The type is AX4E0, so the electron-region geometry is tetrahedral, its hybridization is sp3, and
the bond angles are approximately 109.5°.
Look at C3: The type is AX2E0, so the electron-region geometry is linear, its hybridization is sp, and the
bond angles are approximately 180°.
Look at C4: The type is AX2E0, so the electron-region geometry is linear, its hybridization is sp, and the
bond angles are approximately 180°.
(b) The shortest carbon-to-carbon bond is the triple bond, C3 C4. ≡

(c) The strongest carbon-to-carbon bond is the triple bond, C3 C4. ≡
39. Result: See structures with σ and π bonds designated below
Analyze: Given structural formulas, identify the sigma and pi bonds.
Plan: First, we write the Lewis Structures. The first bond between two atoms must be a σ bond. When more
than one pair of electrons are shared between two atoms, it forms a π bond. So, a single bond is a σ bond; the
second bond in a double bond and the second and third bonds in a triple bond are π bonds.
Execute:
(a) (b)
(c) (d)
40. Result: see structures with σ and π bonds designated below

Analyze: Given structural formulas, identify the sigma and pi bonds.
Plan: Adapt the method described in the solution to Question 39.
(a) (b)
(c)
41. Result: see structure below for location of sigma and pi bonds; (a) 6 sigma bonds (b) 3 pi bonds (c) sp-
hybridization (d) sp-hybridization (e) both have sp2-hybridization
Analyze: Given a Lewis structure, identify the sigma and pi bonds, and the hybridization of several atoms.
Plan: Adapt the method described in the solution to Question 37 and Question 39.
Execute:
H
.. N π
σ C
σ
C
π σ
C σ
π σ
σ H
H
(a) As seen above, the structure has six sigma bonds.
(b) As seen above, the structure has three pi bonds.
(c) Look at the C atom bonded to the N atom: It is of type AX2E0, so the electron-region geometry is linear
and these C atoms have sp-hybridization.
(d) Look at the N atom: It is of type AX1E1, so the electron-region geometry is linear and it has sp-
hybridization.
(e) Both H-bearing C atoms are type AX3E0, so the electron-region geometry is triangular planar and both of
them have a hybridization of sp2.
42. Result: (a) 12 sigma bonds (b) 4 pi bonds (c) sp-hybridization (d) sp2-hybridization (e) sp2-
hybridization
Analyze: Given a Lewis structure, identify the sigma and pi bonds, and the hybridization of several atoms.
Plan: Adapt the methods described in the solutions to Questions 39 and 35.
Execute:
.. C π
σ C H
π σ π σ
C C σ
σ σ
π H H
O C σ σ
σ .. σ
..O σ C H
σ
H
(a) The structure has 12 sigma bonds.
(b) The structure has four pi bonds.
(c) Look at the C atom bonded to the N atom: It is of type AX2E0, so the electron-region geometry is linear
and this C atom has sp-hybridization.
(d) Look at the C atom bonded both O atoms: It is of type AX3E0, so the electron-region geometry is
triangular planar and this C atom has sp2-hybridization.
Look at the C atom bonded to only one O atom: The type is AX4E0, so the electron-region geometry is
tetrahedral this C atom has sp3-hybridization.
(e) Look at the double-bonded O atom: The type is AX1E2, so the electron-region geometry triangular planar
and this O atom has sp2-hybridization.
Molecular Polarity (Section 7-5)

43. Result: Molecules (b) and (c) are polar; HBF2 has the F atoms on partial negative end and the H atom on
the partial positive end; CH3Cl has the Cl atom on partial negative end and the H atoms on the partial
positive end.
Analyze: Identify which molecules are polar and identify the direction of polarity for those that are polar.
Plan: Adapt the plan given in Problem-Solving Example 7.7: Write the correct Lewis structure for each
molecule and use it to assess whether the bonds are arranged symmetrically or unsymmetrically. Use the
periodic table or a table of electronegativities (Figure 6.8) to predict the polarity of the bonds. If the bonds are
polar and arranged unsymmetrically around the central atom, the molecule is polar. The dipole points from the
more electronegative atoms to the less electronegative atoms.
Execute:
First write the Lewis structures and determine the molecular shapes for the molecules:
While the bonds in CO2 and SO3 are polar, the molecules are composed of identical atoms symmetrically
arranged around the central atom, thus (a) and (d) are nonpolar:
HBF2 and CH3Cl have atoms unsymmetrically arranged around the central atom, so we must predict the
polarity of the poles. The bond polarities related to the difference in electronegativity. Use Figure 6.8 to get
electronegativity (EN) values: ENB = 1.9, ENH = 2.1, ENF = 4.0, ENC = 2.4, ENCl = 2.7
ΔENB–H = ENH – ENB = 2.1 – 1.9 = 0.2
ΔENB–F = ENF – ENB = 4.0 – 1.9 = 2.1
ΔENC–H = ENC – ENH = 2.4 – 2.1 = 0.3
ΔENC–Cl = ENCl – ENC = 2.7 – 2.4 = 0.3
All the bonds are polar, so (b) and (c) are polar.
The bond pole arrows’ lengths are related to their ΔEN and the arrows points toward the atom with the larger
EN. So, the B–F arrows are much longer than the HB arrow, and a net dipole points toward the F atoms’ side of
the molecule, making the F atoms’ side of the molecule the partial negative end and the H atom’s side of the
molecule the partial positive end.
The C–Cl arrow points toward Cl, and the C–H points toward the C, so all the arrows point toward the Cl. That
means a net dipole points toward the Cl atom’s side of the molecule, making the Cl atom’s side of the
molecule the partial negative end and the H atoms’ side of the molecule the partial positive end.
44. Result: Molecules (b), (c) and (d) have a net dipole moment; H2S has the S atoms on partial negative end
and the H atom on the partial positive end; CH2Cl2 has the Cl atom on partial negative end and the H
atoms on the partial positive end; HCN has the N atom on partial negative end and the H atoms on the
partial positive end. (see dipole moment diagrams below)
Analyze: Identify which molecules have a net dipole moment and identify the direction of the pole.
Plan: Adapt the plan described in the solution to Question 43.
Execute: First, we write the Lewis structures and determine the molecular shapes for the molecules:
While the bonds in XeF2 are polar, the molecule is composed of identical atoms symmetrically arranged around
the central atom, thus (a) is nonpolar:
H2S, CH2Cl2, and HCN have atoms unsymmetrically arranged around the central atom. None of the atoms have
the same electronegativity (from Figure 6.8: ENH = 2.1, ENS = 2.3, ENC = 2.4, ENCl = 2.7, ENN = 3.0).
Therefore, all the bonds are polar, and we predict that (b), (c), and (d) have a net dipole moment.
The net dipole in the molecules point toward the atoms with higher electronegativity and away from the atoms
with low electronegativity:
45. Result: (a) The Br–F bond has a larger electronegativity difference. (b) The H–O bond has a larger
electronegativity difference.
Analyze: Given chemical formula and dipole moment, explain the differences in the dipole moments.
Execute: The bond polarities are related to the difference in electronegativity.
Use Figure 6.8 to get electronegativity (EN) values: ENBr = 2.6, ENF = 4.0, ENCl = 2.7
ΔENBr–F = ENF – ENBr = 4.0 – 2.6 = 1.4
ΔENBr–Cl = ENCl – ENBr = 2.7 – 2.6 = 0.1
The bond polarity in BrF is much greater than in BrCl, which explains the significant dipole moment difference.
Use Figure 6.8 to get electronegativity (EN) values: ENH = 2.1, ENO = 3.4, ENS = 2.3
ΔENO–H = ENO – ENH = 3.4 – 2.1 = 1.3
ΔENS–H = ENS – ENH = 2.3 – 2.1 = 0.2
The bond polarity of the O–H bonds is much greater than that of the S–H bonds, which explains the dipole
moment difference.
46. Result: Both molecules have dipole moments. (a) NH2OH has the O atom on the partial negative end
and the H atoms on the partial positive end. (b) S2F2 has the F atoms on the partial negative end and
the S atoms on the partial positive end.
Analyze: Identify which molecules are polar and identify the direction of the dipole moment.
Execute:
(a) The Lewis structure/geometry has polar O–H, N–H, and N–O bonds.
ΔENO–H = ENO – ENH = 3.4 – 2.1 = 1.3
ΔENN–H = ENN – ENH = 3.0 – 2.1 = 0.9
ΔENN–O = ENO – ENN = 3.4 – 3.0 = 0.4
(b) The Lewis structure/geometry has polar S–Cl bonds.

ΔENCl–S = ENCl – ENS = 2.7 – 2.3 = 0.4
47. Result: Both molecules have net dipole moments. (a) FNO has the F atoms on the partial negative end
and the O atom on the partial positive end. (b) S2F2 has the F atoms on the partial negative end and the
S atoms on the partial positive end.
Analyze: Identify which molecules have a net dipole moment and identify the direction of the pole.
Execute: (a) The Lewis structure/geometry has polar F–N and N–O bonds:
ΔENF–N = ENF – ENN = 4.0 – 3.0 = 1.0
ΔENN–O = ENO – ENN = 3.4 – 3.0 = 0.4
(b) The Lewis structure/geometry has polar F–S bonds:

ΔENF–S = ENF – ENS = 4.0 – 2.3 = 1.7
Noncovalent Interactions (Section 7-6)

48. Result/Explanation: Use information provided in Section 7-6 to construct this table:
Noncovalent Interaction Strength Example
ion-ion Greatest strength Na+ interaction with Cl –
ion-dipole High strength Na+ ions in H2O
dipole-dipole medium strength H2O interaction with H2O
dipole-induced dipole Low strength H2O interaction with Br2
induced dipole-induced dipole Lowest strength Br2 interaction with Br2
49. Result: Water and ethanol interact using the same kinds of intermolecular forces (i.e., both experience H-
bonding); whereas, water and cyclohexane interact with significantly different intermolecular forces.
Analyze: Given molecular formulas and a description of variable miscibility, explain using molecular structure
and noncovalent interactions the miscibility.
Plan and Execute: The electronegativity of O and C are fairly different (3.4 and 2.4, respectively), so the C–O
bonds in (CH3)2O are quite polar. Thus, H2O and (CH3)2O will be able to interact using hydrogen bonding
(shown below) and these two substances would remain mixed together when combined (i.e., they are miscible).
The bonds in (CH3)2S are not very polar, because the electronegativities of S and C are similar (2.3 and 2.4,
respectively). None of the atoms in (CH3)2S can form hydrogen bonds with water. Water molecules are highly
polar. To interact with (CH3)2S, water would have to sacrifice hydrogen bonding with other water molecules.
Without comparably strong interactions, these two substances will not stay mixed together when combined.
Thus it makes sense that (CH3)2S is only slightly water soluble.
50. Result: water and ethanol interact using the same kinds of intermolecular forces (i.e., both experience H-
bonding); whereas, water and cyclohexane interact with significantly different intermolecular forces.
Analyze: Given molecular formulas and a description of variable miscibility, explain using molecular structure
and noncovalent interactions the miscibility.
Plan and Execute: The electronegativity of O and C are fairly different (3.4 and 2.4, respectively), so the C–O
bond in CH3CH2OH are quite polar. Thus, H2O and CH3CH2OH will be able to interact using hydrogen
bonding (shown below) and these two substances would remain mixed together when combined (i.e., they are
miscible).
Cyclohexane is a six-carbon-ring hydrocarbon, C6H12. The bonds in C6H12 are not very polar. None of the
atoms in C6H12 can form hydrogen bonds with water. Water molecules are highly polar. To interact with
C6H12, water would have to sacrifice hydrogen bonding with other water molecules. Without comparably
strong interactions, these two substances will not stay mixed together when combined. Thus it makes sense that
C6H12 is not miscible in water.
51. Result: Wax is non-polar. Water droplets will form so that the polar water molecules can avoid
interaction with the wax. Dirty, unwaxed cars have surface soils and salts that interact well with water.
Analyze, Plan, and Execute: Wax is made up of nonpolar molecules that interact almost exclusively with
London forces. The water molecules are highly polar and would have to give up hydrogen bonds between
other water molecules to interact with wax using the much weaker London forces. These two substances would
not interact very well. The water “beads up” in an attempt to have the smallest possible necessary surface
interaction with the wax. On a dirty, unwaxed car, the soils and salts that are often found on cars contain ions
and polar compounds. They interact much more readily with water, so the water would not “bead up” on the
dirty surface.
52. Result: Tar is non-polar. A non-polar solvent, kerosene, will work better to dissolve the tar than the
polar solvent, water.
Analyze, Plan, and Execute: Tar is made up of nonpolar molecules that interact almost exclusively with
London forces. The water molecules are highly polar and would have to give up hydrogen bonds between other
water molecules to interact with tar using only much weaker London forces. Water would not dissolve tar, so it
would not be a good solvent to use. The kerosene molecules are non-polar and would interact using London
forces. These two substances would be miscible, and kerosene would be a good solvent to remove tar.
53. Result: (c) and (d)
Analyze: Given condensed structural formulas, determine which can form intramolecular hydrogen bonds.
Plan: A hydrogen bond forms between (1) a very electronegative atom and (2) a H atom that is bonded to a
very electronegative atom (EN ≥ 3.0). Intramolecular hydrogen bonding occurs only within a molecule that has
both of these features nearby each other positioned so they can interact without significantly straining the
geometric structure.
Execute:
(a) CH2Br2 does not contain any atoms with EN ≥ 3.0, so this molecule cannot form any hydrogen bonds.
(b) CH3OCH2CH3 has only one O atom and all its H atoms are bonded to C atoms, so this molecule cannot
form intramolecular hydrogen bonds.
(c) H2NCH2COOH has three different H atoms are bonded to high electronegativity atoms (ENO = 3.5 and
ENN = 3.0).
One of the H atoms bonded to the N atom can form an intramolecular hydrogen bond with the nearby O
atom. One of those H atoms bonded to O can form an intramolecular hydrogen bond with the nearby N
atom in the structure. Two of the possible structures are shown here:
(d) H2SO3 has H atoms that are bonded to high electronegativity O atoms (EN = 3.5). Those H atoms might be
able to form hydrogen bonds with the nearby O atom. This interaction does appear to put some strain on
the 109.5° angles, but S atom is from the third period, so it’s large size might help permit the O atom to
keep its tetrahedral angle.
(e) CH3CH2OH has only one O atom, so this molecule cannot form intramolecular hydrogen bonds.
54. Result: See structures below

Analyze: Given condensed structural formulas, determine which can form intramolecular hydrogen bonds.
Plan: Interpret the molecular formula given to determine the Lewis Structure, then adapt the plan used in the
solution to Question 53.
Execute:
intramolecular intramolecular
intermolecular
55. Result: (b) < (c) < (d) < (a); Hydrogen bonding interactions are stronger than dipole-dipole interactions
and London forces are the weakest. London forces increase as the number of electrons increases.
Analyze: Given condensed structural formulas, explain the order of their increasing boiling point.
Plan: Boiling points are higher when the interactive forces are stronger. Determine the structural elements that
relate to polarity and the types of noncovalent intermolecular forces each molecule can employ.
Execute:
(a) (b) (c) (d)
CH3CH2OH is only molecule that can interact with hydrogen bonding, the strongest intermolecular force, due
to the O–H bond. Of the remaining three molecules, CH3OCH3 is the most polar, since the C–O bonds are very
polar. It interacts with dipole-dipole forces. The remaining two molecules are nonpolar and they interact via
London forces. London forces are stronger when the molecule has more electrons, so the CBr3CBr2CBr3 has
stronger London forces than CH3CH2CH3. The molecule with the lowest boiling point is CH3CH2CH3,
followed by CH3OCH3, and the highest boiling point is CH3CH2OH, so the order of increasing boiling point is:
(b) < (c) < (d) < (a)
56. Result: He > Ne > Ar > Kr > Xe > Rn; the number of electrons increases down a group and the London
forces increase with increasing number of electrons.
Analyze: Given a set of elements, explain the order of their increasing boiling point.
Execute:
The noble gases are Group 8 elements: He, Ne, Ar, Kr, Xe, and Rn. These substances are monatomic, so they
interact exclusively using London forces. London forces are stronger when the atom has more electrons. On the
periodic table, the atoms lower in the group have more electrons than the atoms higher in the group, so Rn is the
largest and He is the smallest. Boiling points increase as the interactive forces increase, so the order of
increasing boiling point for nobel gases is the same as order of size.
57. Result: Vitamin C is capable of forming hydrogen bonds with water, thus vitamin is miscible in H2O.
Analyze: Given a structural formula and solubility details, explain at the molecular level the solubility.
Execute: Four H atoms are bonded to high electronegativity O atoms (EN = 3.5). Those H atoms (circled in the
structure below) can form hydrogen bonds with H2O molecules.
This molecule is quite polar and would not interact well with fats, because fats interact primarily using London
forces.
58. Result: Vitamin E interacts primarily with London forces due to the long hydrocarbon chain. Fats
interact primarily using London forces, so Vitamin E will dissolve in fat. Water interacts primarily with
H-bonding forces, so water would not dissolve Vitamin E.
Analyze: Vitamin E is a large molecule that contains a long hydrocarbon chain. Comparatively, its structure
provides very few ways to undergo dipole-dipole or hydrogen bonding interactions. Because of its size and
composition, it interacts primarily with London forces. Fats interact primarily using the same London forces, so
Vitamin E would dissolve in fats.
In contrast, water molecules would have to give up hydrogen bonds among other water molecules and use only
London forces to interact with a large part of the Vitamin E molecule. Hence water would not dissolve Vitamin
E.
59. Result: Molecule (c), C3H8, would be the most soluble in cyclohexane, since both interact via London
forces; NaCl would be the least soluble, because the ions would not be attracted to the non-polar solvent.
Analyze, Plan, and Execute: Cyclohexane, a six-carbon-ring hydrocarbon, has no capability of forming
hydrogen bonds. Because of its size, it interacts primarily with London forces. The symmetry of the molecule
and the only slightly polar bonds give it very little capacity for dipole-dipole interactions.
Molecule (c), C3H8, is also an alkane, and for the same reasons, interacts with the same types of forces as
cyclohexane. It would be more soluble in cyclohexane than NaCl or CH3CH2OH.
NaCl is composed of ions, which would interact well only with other ions or highly polar substances. While
CH3CH2OH does have the capability of forming hydrogen bonds, it also has a hydrocarbon end, which interacts
with the same types of forces as cyclohexane. Therefore, the least soluble is NaCl.
60. Result: (a) London forces (b) London forces (c) Covalent bonds (d) Dipole-dipole forces
(e) Intermolecular hydrogen bonding forces
Analyze, Plan, and Execute:
(a) Hydrocarbons have no capability of forming hydrogen bonds and the bonds are close to non-polar. The
molecules interact primarily with London forces. The London forces between the molecules must be
overcome to sublime C10H8.
(b) As described in (a), propane molecules, a hydrocarbon, would need to overcome London forces to melt.
(c) Decomposing molecules of nitrogen and oxygen require breaking covalent bonds, so the forces that must
be overcome are the covalent intramolecular forces.
(d) To evaporate polar PCl3 requires that the molecules overcome dipole-dipole forces.
(e) The double strands of DNA are shown in Figure 7.27. The interaction between the two strands are
hydrogen bonds. These hydrogen bonding forces must be overcome to “unzip” the DNA double helix.
Biomolecules (Section 7-7)
61. Answer/Explanation: The structure of a section of DNA with T-C-G

CH3
H
H O H
N N
CH2
O N N CH2
N O
H N
H H
H H H
O N
OH H
T A OH
O
O H O P O
H N H O N
O P O H O
O CH2
H N
N H N O
CH2 H H
O N
N
H
H H N OH
O H
H O
H G
OH C
O P O
H
O
N O H N H
H
O P O
O
O N H
N H N
N CH2
CH2 N O
O
N H O H H
H H
H H
H
OH G C OH
O
O
O P O
O P O
O
O
CH2
CH2
62. Answer/Explanation: G-C interacts with three hydrogen bonds; whereas, A-T interacts with only two hydrogen
bonds. Stronger attractive forces require higher melting temperature.
Molecular Structure Determination by Spectroscopy

63. Result: Compared to UV: (a) IR has lower energy, (b) IR has longer wavelength, (c) IR has lower
frequency.
Explanation:
(a) IR radiation is lower in energy than UV radiation. (IR is below visible spectrum and UV is above it).
(b) IR radiation have longer wavelength than UV radiation. (Lower energy waves have longer wavelength
than higher energy waves.).
(c) IR radiation has lower frequency than UV radiation. (Lower energy waves have smaller frequency than
higher energy waves).
64. Result: (a) pi electrons (b) vibrational motions in molecules
Explanation: The Tools of Chemistry: Infrared Spectroscopy in Section 7-2d describes infrared spectroscopy.
The Tools of Chemistry: Ultraviolet-Visible Spectroscopy in Section 7-5 describes ultraviolet-visible
spectroscopy.
(a) Ultraviolet and visible spectroscopy are described together and some of the given examples that
specifically talk about what electrons are involved refer to visible light. The electrons that would be
affected by ultraviolet light (or high-energy visible light) are d electrons in some transition metals and pi
electrons in the double bonds of organic compounds.
(b) Infrared spectroscopy tells us about the frequencies of specific vibrational motions in molecules.
65. Result: (a) C–C stretch (b) O–H stretch
Explanation: The Tools of Chemistry: Infrared Spectroscopy in Section 7-2d describes infrared spectroscopy.
Wavelength, λ, is the variable on the horizontal axis of the spectrum shown. Wavelength is inversely
proportional to energy. So, longer wavelength light has lower energy and shorter wavelength light has higher
energy.
(a) The lowest energy motion described in the spectrum is C–C stretch.
(b) The highest energy motion described in the spectrum is O–H stretch.
66. Result: 427 nm and 483 nm; 427 nm is the more energetic transition
Explanation: Two “shoulders” on either side of the main peak can be estimated to be found at 427 nm and 483
nm. Because shorter wavelength indicates higher energy light, the 427 nm peak is the more energetic transition.
General Questions
67. Result: (a) Angle 1: 180° Angle 2: 109.5° Angle 3: 109.5° (b) C=O (c) C=O (d) C=C
Analyze: Given a Lewis Structure, determine a few indicated bond angles and identify the most polar bond, and
the shortest CO and CC bonds.
Plan and Execute: Follow the plans from the solution to Questions 32 - 35 and 43.
(a) Angle 1: Look at the C atom bonded to the N atom: It is of type AX2E0, so the electron-region geometry
is linear and this C atom has sp-hybridization. The sp-hybridized C atoms have linear bond angles of
approximately 180°. So, the CCN angle is 180°.
Angles 2 and 3: Look at the C atom bonded to only one O atom: The type is AX4E0, so the electron-
region geometry is tetrahedral this C atom has sp3-hybridization. The sp3-hybridized C atom has
tetrahedral bond angles of approximately 109.5°. So, the HCH angle (Angle 2) and the OCH angle
(Angle 3) are both 109.5°.
(b) The most polar bond is the C=O bond.
(c) Multiple bonds are shorter than single bonds, so the C=O bond is the shortest CO bond:
(d) Multiple bonds are shorter than single bonds, so the C=C bond is the shortest CC bond:
68. Result: (a) Angle 1: 180° Angle 2: 120° Angle 3: 120° (b) C≡N
Analyze: Given a Lewis Structure, determine a few indicated bond angles and identify the most polar bond.
Plan and Execute: Follow the plans from the solution to Questions 32 - 35 and 43.
(a) Angle 1: Look at the C atom bonded to the N atom: It is of type AX2E0, so the electron-region geometry
is linear with sp-hybridization and NCC bond angles of approximately 180°.
Angles 2 and 3: Look at the C atoms double bonded to each other: The type for each C atom is AX3E0, so
the electron-region geometry is triangular planar with sp2-hybridization and both the HCH angle (Angle 2)
and the CCH angle (Angle 3) are approximately 120°.
(b) The most polar bond is the C≡N bond.

69. Result: (a) See structure below (b) Angle 1: 180° (c) Angle 2: 180°
Analyze: Given a chemical formula, write the Lewis structure and determine the CCO and CCC bond angles.
Plan and Execute: Follow the plans from the solutions to Question 6.15 and Questions 32 - 35..
(a)
(b) Angle 1: Look at a C atom bonded to the O atom: It is of type AX2E0, so the electron-region geometry is
linear with sp-hybridization and CCO bond angle of approximately 180°.
(c) Angle 2: Look at the C atom bonded only to the C atoms: It is of type AX2E0, so the electron-region
geometry is linear with sp-hybridization and CCO bond angle of approximately 180°.
70. Result: See structures below; (a) Tetrahedral; tetrahedral (b) Electron region geometry on O atom is
tetrahedral and the geometry at O atom is angular (bent); electron region geometry and molecular
geometry on S atom are both octahedral (c) The electron arrangement around each S is tetrahedral; the
geometry around each S is triangular pryamidal (d) Octahedral; square planar
Analysis: Write Lewis structures for a list of chemical formulas and use VSEPR to determine their electron-
region geometry and the molecular geometry.
Execute:
(a) PSCl3 (32 e–) The type is AX4E0, so the electron-region geometry is tetrahedral and the
molecular geometry is tetrahedral.
(b) SOF6 (54 e–) On the O atom, the type is AX2E2, so the electron-region geometry is
tetrahedral and the geometry around the O atom is angular(bent).
On the S atom, the type is AX6E0, so the electron-region geometry is
octahedral and the molecular geometry around the S atom is
octahedral.
(c) S2O42– (38 e–) On each S atom, the type is AX3E1, so the electron-region geometry is
tetrahedral and the geometry on each S atom is triangular pyramidal.
(d) TeF42– (36 e–) The type is AX4E2, so the electron-region geometry is octahedral and
the molecular geometry is square planar.
71. Result: (a) See structure below (b) Angle 1: 180° (c) Angle 2: 180°
Analyze: Given a chemical formula, write the Lewis structure and determine the CCO and CCC bond angles.
Plan and Execute: Follow the plans from the solutions to Question 6.15 and Questions 32 - 35.
(a)
(b) Angle 1: Look at a C atom bonded to the O atom: It is of type AX2E0, so the electron-region geometry is
linear with sp-hybridization and CCO bond angle of approximately 180°.
(c) Angle 2: Look at the C atom bonded only to the C atoms: It is of type AX2E0, so the electron-region
geometry is linear with sp-hybridization and CCO bond angle of approximately 180°.
72. Result: It will absorb visible light because it has an extended pi-system.
Explanation: The Tools of Chemistry: Ultraviolet-Visible Spectroscopy in Section 7-5 describes ultraviolet-
visible spectroscopy. Compounds with an extended pi system formed by conjugation between a series of
alternating double bonds absorb visible light. This molecule also has an extended pi system, so we would
predict it absorbs visible light.
73. Result: (a) see structure below (b) each C has sp2-hybridization. (c) Inconsistent, since angles are 90° not
120°
Analyze: Given a chemical formula, write the Lewis structure and determine the hybridization of indicated
atoms, then discuss the inconsistency between the molecular shape and the predicted bond angles.
(a) C4O42– (42 e–) has four equivalent resonance structures. One of these resonance structures looks like this:
.. .O. ..
O ..
2-
.. ..
C C
C C
.O .
.. .O. .
(b) Look at each C atom: The type for each C atom is AX3E0, so the electron-region geometry is triangular
planar and each C atom has sp2-hybridization.
(c) There is an inconsistency. If the C atoms have sp2-hybridization, the C–C–C bond angle would be 120°;
however, the square structure in (a) requires that the C–C–C bond angles must be 90°.
74. Result: (a) see structure below (b) each C has sp2-hybridization (c) Yes. The resonance hybrid indicates
that all the p-orbitals in the pi-bonds must be parallel (pz ), so the sigma bonds are all in the x-y plane.
Analyze: Given a chemical formula, write the Lewis structure and determine the hybridization of indicated
atoms, then explain whether the molecule is planer or not.
(a) C5O52– (52 e–) has five equivalent resonance structures. One of these resonance structures looks like this:
.. . 2-
O.
.. O.. C
.. .
O.
C C
C C
.. O .. .O.
.. ..
(b) Look at each C atom: The type for each C atom is AX3E0, so the electron-region geometry is triangular
planar and each C atom has sp2-hybridization.
(c) The croconate ion is planar because the maximum number of resonance structures can only exist if all the
p-orbitals used for the pi-bonds are parallel (say, pz); therefore the sp2-hybrid orbitals all must use the px
and py orbitals, and the molecule’s sigma bonds are all in the x-y plane.
75. Result: (a) For HCl: 2.69 × 10–20 C; For HF: 6.95 × 10–20 C (b) partial negative charge on F is larger
than that on Cl, so F has a higher EN.
Analyze: Given dipole moments and bond lengths for two dipolar molecules, calculate the quantity of charge in
coulombs that is separated by the bond length in each and use the result to show that one atom is more
electronegative than another.
Plan and Execute: Dipole moment is determined by multiplying the partial charge by the bond length.
µ = (δ+) × (bond length)
For HCl:
µ 3.43× 10−30 C ⋅ m 1 pm
δ+ = = × = 2.69 × 10−20 C
bond length 127.4 pm 10−12 m
For HF:
µ 6.37 × 10−30 C ⋅ m 1 pm
€ δ+ = = × = 6.95× 10−20 C
The partial charges in the HF bond are larger than those of the HCl bond, indicating that the fluorine is more
electronegative than chlorine.
€
76. Result: 1.32 × 10–19 C; this partial charge is 81.6% of a full negative charge of an electron, so KF is not
really completely ionic.
Analyze: Given dipole moments and bond lengths for two dipolar molecules, calculate the partial charge on
each atom, then compare results with the charge of an electron and determine if a compound is completely
ionic.
Plan and Execute: The definition of dipole moment was given in Question 75:
µ = (δ+) × (bond length)
µ 28.7 × 10−30 C ⋅ m 1 pm
For KF: δ+ = = × = 1.32 × 10−19 C
δ– = – 1.32 × 10–19 C
If the bond were completely ionic, then the partial negative charge on fluorine would be the same as the charge
€
on the electron (–1.62x10–19 C). So, KF is not completely ionic.
−1.32 × 10−19 C
Percent of full negative charge = × 100 % = 81.6 % = 81.6% of a full negative charge.
−1.62 × 10−19 C
77. Result: Polar, if EN’s of the two atoms are different; non-polar, if the EN’s of the two atoms are the
same.
Explanation: A diatomic€ molecule is nonpolar if the atoms that it is composed of have the same
electronegativity. The only way to be sure of identical electronegativity is for the two atoms to be the same. A
diatomic molecule is polar when the two atoms it is composed of have different electronegativities.
78. Result: If the two atoms are the same element, then the molecule will be nonpolar. If the two atoms have
different EN’s, the molecule will be polar.
Explanation:
A diatomic molecule can have a dipole moment of zero if the atoms have the same electronegativity, such as
when they are atoms of the same element. O2 is a good example of a nonpolar diatomic molecule.
If the two atoms have different electronegativities, then the molecule will have a nonzero dipole moment and
the molecule will be polar. CO is a good example of a polar diatomic molecule.
79. Result: (a) Box A, B, D, and H (b) Boxes D, G, and H (c) Boxes A and G (d) Boxes E and I (e) Boxes B,
C, D, E,F, H, and I (f) Box A (g) Box F (h) Box H (i) Box A (j) Box F and G
Analyze and Plan: Given several choices of chemical formulas, find the answer for each prompt related to
electron-region geometry, shape, hybridization, and physical properties. To answer several of these prompts,
we must write the Lewis Structures and determine the electron-region geometries and molecular geometries for
each structure. Follow the plans from the solutions to Question 6.15 and Questions 32 - 35.
Execute:
A (10 e–) B (26 e–) C (8 e– and 26e–)
or
D (8 e–) E (16 e–) F (14 e–)
G (8 e– and 14 e–) H (8 e–) I (20 e–)
or
(a) The structures that have electron-region geometry the same as the molecular geometry are the structures
with no lone pairs on the central atom. These are seen in Box A with a linear geometry (AX2E0) and Boxes
B, D and H with a tetrahedral geometry (AX4E0). In Box G, both of the two structures qualify (with a
linear geometry), so it is appropriate to include Box G in the answer, as well.
(b) Non-polar molecular structures have the same atoms bonded to the central atom and no lone pairs on the
central atom, so that all the bond poles balance and result in a zero net dipole moment. These are
represented in Boxes D and H with the bonding type of AX4E0. One of the two structures in Box G also
qualifies (F2). Since that box indicates that one or the other structure could answer the prompt, it is logical
to include Box G in the answer, as well.
(c) The structures that have linear geometry have bonding type of AX2E0 or are diatomic molecules. These are
seen in Box A with bonding type of AX2E0 and Box G with two diatomic molecules.
(d) The structures that have angular (bent) geometry have bonding type of AX2E2 or AX2E1. These are seen in
Box E and I, both with bonding type of AX2E2.
(e) The central atom is sp3-hybridized in structures with the bonding type of AX4E0, AX3E1, or AX2E2. Boxes
B, D and H have the central atom with the AX4E0 bonding type. Boxes C and F have the central atom
with the AX3E1 bonding type. Boxes E and I have the central atom with the AX2E2 bonding type.
(f) The central atom has sp-hybridization in structures with the bonding type of AX2E0. Box A has the central
C atom with an AX2E0 bonding type.
(g) Take each pair of molecules given in the grid and compare them. The liquid with the lowest boiling point
will be composed of molecules with the strongest intermolecular forces. Box F has a molecule that would
interact using both dipole-dipole intermolecular forces and hydrogen bonding intermolecular forces. The
only other molecule in the grid that can undergo hydrogen bonding forces is HF (one of the choices in Box
G). Since HF is smaller and has fewer atoms, NH2Cl would compose the liquid with the lower boiling
point when compared to any other molecule in the chart. The answer is Box F.
(h) Take each pair of molecules given in the grid and compare them. The liquid with the highest vapor
pressure will be composed of molecules with the weakest intermolecular forces. Boxes D and H have
molecules that would interact using only London intermolecular forces. The only other nonpolar molecule
in the box that is non-polar is F2 (one of the choices in Box G). Since CH4 has fewer electrons than SiH4
or F2 it probably has weaker London forces, and so would compose the liquid with the higher vapor
pressure when compared to any other molecule in the chart. The answer is Box H.
(i) Take each pair of molecules given in the grid and compare them. To determine relative dipole moments,
start with the change in electronegativity ΔEN to estimate relative bond polarity. Boxes A and F contain
the widest range of electronegativities. ENF = 4.0, ENN = 3.0, ENCl = 2.7, ENC = 2.4, ENH = 2.1. While
the N-H bonds are more polar (in Box F), the pair will partially cancel each other out, pulling electrons in
different directions.
There is one other highly polar molecule in Box G: H-F has the largest ΔEN, and would therefore be
predicted to have the higher dipole moment.
So, technically, the most polar molecule in the grid is found in Box G. However, there is a non-polar
molecule also in Box G that has a zero dipole moment, F2, and the molecules in both Box A and F have
greater dipole moments than a molecule in Box G. Therefore, aside from HF, the most polar molecule in
the grid is HCN in Box A.
(j) Several of the structures are polar, which is the prerequisite for dipole-dipole intermolecular forces;
however only two molecules, HF (one of the two molecules in Box G) and NH2Cl (in Box F) have an H
atom bonded to a high-electronegativity atom; therefore, both Boxes F and G qualify to answer this
prompt.
80. Result: (a) Box A, C, D, E, F, G, and H (b) Boxes C, E, and F (c) Boxes D, E and G (d) Box H (e) Boxes
A, B, F and I (f) Box H (g) Box I
Analyze and Plan: Adapt the plan used in Question 79.
Execute:
A (8 e–) B (26 e–) C (40 e–)

D (16 e–) E (16 e–) F (26 e– and 40 e–)
or
G (14 e– and 28 e–) H (24 e–) I (14 e–)
or
(a) The structures that have electron-region geometry the same as the molecular geometry are the structures
with no lone pairs on the central atom. These are seen in Box A with a tetrahedral geometry (AX4E0), Box
C with a triangular bipyramidal geometry (AX5E0), Boxes D and E with linear geometry (AX2E0), and
Box H with a triangular planar geometry (AX3E0). In Boxes F and G, one of the two structures qualifies
(PF5 as explained in Box C and diatomic ClF with a linear geometry). Since those boxes indicate that one
or the other structure could answer the prompt, it is appropriate to include Boxes F and G in the result, too.
(b) Non-polar molecular structures have the same atoms bonded to the central atom and no lone pairs on the
central atom, so that all the bond poles balance and result in a zero net dipole moment. These are
represented in Box C with the bonding pattern of AX4E0 and Box E with the bonding pattern of AX2E0.
One of the two structures in Box F also qualifies (PF3 as explained in Box C). Since that box indicates that
one or the other structure could answer the prompt, it is logical to include Box F in the answer, as well.
(c) The molecules with linear geometry have AX2E0 structures. Boxes D and E both qualify. One of the two
structures in Box G also qualifies (ClF). Since that box indicates that one or the other structure could
answer the prompt, it is logical to include Box G in the result, as well.
(d) Trigonal planar geometry has the bonding type of AX3E0. Box H has the bonding type of AX3E0.
(e) The central atom has sp3-hybridization in structures with the bonding type of AX4E0, AX3E1, or AX2E2.
Boxes A and B have the central P atom with AX4E0 and AX3E1 bonding types, respectively. One of the
two structures in Box F also qualifies (PF3 has the central P atom with AX3E1). Since that box indicates
that one or the other structure could answer the prompt, it might be logical to include Box F in the answer,
as well. Box I has a molecule with two central atoms. The N atom and O atom have AX3E1 and AX2E2
bonding types, respectively, so technically Box I also qualifies for this prompt.
(f) The central atom has sp2-hybridization in structures with the bonding type of AX3E0 or AX2E1. Box H has
the central N atom with an AX3E0 bonding type.
(g) Several of the structures are polar, which is the prerequisite for dipole-dipole intermolecular forces;
however only one molecule has an H atom bonded to a high-electronegativity atom, which is the
prerequisite to having hydrogen bonding intermolecular forces. Therefore, only Box I qualifies to answer
this prompt.
Applying Concepts
81. Result: CH3SH has weaker IM forces.
Analyze: Given two chemical formulas and two boiling points, explain the differences.
Plan: Write the Lewis Structures and determine the electron-region geometries and molecular geometries for
each structure. Follow the method described in the solutions to Question 6.15 and Questions 32 - 35.Determine
intermolecular forces for each molecule and relate to the properties as described in Section 7-6.
Execute: The two molecules have the same geometry, since O and S are in the same periodic group:
The lower electronegativity of S (2.3) makes the S–H bond essentially nonpolar, unlike the O–H bond. In the
liquid state, a molecule of CH3OH interacts with other CH3OH molecules using hydrogen bonds, dipole-dipole,
and London forces. Liquid CH3SH molecules only interact with London forces, which are much weaker. The
boiling point of CH3SH is lower because it has weaker intermolecular forces.
82. Result: N2 has weaker IM forces.
Analyze: Given two chemical formulas with the same number of electrons, explain the differences in their
melting and boiling points.
Plan: Adapt the plan used in the solution to Question 81.
Execute: The two molecules have the same geometry:
The N2 molecule is nonpolar. Because C atoms and O atoms have different electronegativities, the CO
molecule is polar. In the condensed states, a molecule of CO interacts with other CO molecules using dipole-
dipole forces and London forces; whereas, N2 molecules only interact with London forces, which are weaker.
The melting and boiling point of N2 are lower because it has weaker intermolecular forces.
83. Result: (a) See structure below, 120° (b) 180° (c) sp2, sp3 (d) See structures below; sp2, sp2, sp3; sp3; sp2,
sp2
Analyze and Plan: Given a name and chemical formula for a molecules, write a Lewis structure, estimate a
bond angle, identify the hybridization for one atom, draw resonance structures for a related compound, and
identify the hybridization of some atoms in it. Adapt the plan used in the solution to Questions 32-35.
(a) Determine the Lewis structure knowing that C–N–N–N is part of the structure (based on angles requested
in this and later parts). The structure has 40 e–. Two resonance structures exist. This is one of them:
The central N in the N-N-C angle has AX2E1 type bonding, so the bond angle is 120°.
(b) The central N in the N-N-N angle has AX2E0 type bonding, so the bond angle is 180°.
(c) The N atoms next to the C atom has AX2E1 type bonding, so that means sp2-hybridization is needed. The
C atom has AX4E0 type bonding, so it needs sp3-hybridization.
(d) The new H atoms will react with the electrons of a π-bond. The product has two predominant resonance
structures with the lowest formal charges, shown here:
There are other possible answers.

From left to right: In the first structure, the first N atom has AX2E1 type bonding, so that means the
N atom has sp2-hybridization, the next N atom has AX3E0 type bonding, so that means the N atom
has sp2-hybridization, and the end N atom has AX2E2 type bonding, so that means the N atom has
sp3-hybridization. In the second structure, the first N atom has AX2E2 type bonding, so that means
the N atom has sp3-hybridization, the next N atom has AX3E0 type bonding, so that means the N
atom has sp2-hybridization, and the end N atom has AX2E1 type bonding, so that means the N atom
has sp2-hybridization.
84. Result: (a) see structures below (b) sp, sp
Analyze: Adapt the plan used in the solution to Questions 32-35 and Problem-Solving Example 7.6.
–
(a) Determine the Lewis Structures of N3 with 16 electrons:
(b) The bonding type is AX2E0 so an sp-hybridization is needed for each central N atom, leaving two
unhybridized p-orbitals for the formation of π-bonds to each of the terminal N atoms.
85. Result: See the last three columns of the table below
Analyze: Determine Lewis structure and the AXE type, to determine geometry and hybridization.
Molecule Number of Lewis structure Type Electron- Molecular Bond
or Ion electrons region geometry angles
AXnEm
geometry
ICl2+ 7 + 2(7) – 1 AX2E2 tetrahe- Angular 109.5°

dral (bent)
= 20
triangular
bipyra-
I 3– 3(7) + 1 AX2E3
midal
linear 180°
= 22
ICl3 7 + 3(7) AX3E2 triangular T-shaped 90°

bipyra-
= 28
midal
ICl4– 7 + 4(7) + 1 AX4E2 octahedral square 90°

planar
= 36

or Ion electrons region geometry angles
AXnEm
geometry
IO4– 7 + 4(6) + 1 AX4E0 tetrahe- tetrahe- 109.5°

dral dral
= 32
IF4+ 7 + 4(7) – 1 AX4E1 triangular seesaw 120° and

bipyra- 90°
= 34
midal
IF5 7 + 5(7) AX4E1 octahedral square 90°

pyramid
= 42
IF6+ 7 + 6(7) – 1 AX6E0 octahedral octahedral 90°

= 48
86. Result: See the last three columns of the table, below
Analyze: Determine Lewis structure and the AXE type, to determine geometry and hybridization.
or Ion electrons region geometry angle
AXnEm
geometry
SO2 6 + 2(6) AX2E1 triangular angular 120°
planar (bent)
= 18
SCl2 6 + 2(7) AX2E2 tetrahe- angular 109.5

dral (bent)
= 20
SO3 6 + 3(6) AX3E0 triangular triangular 120°

planar planar
= 24

or Ion electrons region geometry angle
AXnEm
geometry
SO32– 6 + 3(6) + 2 AX3E1 tetrahe- triangular 109.5°

dral pyramidal
= 26
SF4 6 + 4(7) AX4E1 triangular seesaw 120° and

bipyra- 90°
= 34
midal
SO42– 6 + 4(6) + 2 AX4E0 tetrahe- tetrahe- 109.5°

dral dral
= 32
SF5+ 6 + 5(7) – 1 AX5E0 triangular triangular 120° and

bipyra- bipyra- 90°
= 40
midal midal
SF6 6 + 6(7) AX6E0 octahedral octahedral 90°

= 48
87. Result: (a) dipole-dipole and H-bonding forces (b) polar covalent bonds (c) dipole-dipole and
H-bonding forces (d) dipole-dipole forces
Analyze: Determine the types of forces that are overcome during various changes.
Plan: Adapt the plans used in the solutions to Questions 49-53.
Execute:
(a) Molecules of liquid methanol (CH3OH) interact via dipole-dipole interactions and hydrogen bonding.
These intermolecular forces must be overcome to evaporate liquid methanol.
(b) Decomposing molecules into other molecules requires breaking covalent bonds, so the forces that must be
overcome are the intramolecular covalent forces. The structural formula for the reactant molecule looks
like this: The product molecules look like this: and .
Some of the polar covalent O–O and O–H bonds in the reactant must be broken to make some of the new
bonds in the products.
(c) Molecules of solid urea (H2NCONH2) interact via dipole-dipole interactions and hydrogen bonding (shown
below). Some of these intermolecular forces must be overcome to melt solid urea.
(d) Molecules of liquid HCl interact via dipole-dipole interactions. These intermolecular forces must be
overcome to boil liquid HCl.
88. Result: The molecules are polar, so they interact using dipole-dipole forces.
Analyze: Given names and chemical formulas of miscible compounds, explain, on a molecular bases, why they
are miscible.
Plan: Adapt the plans used in the solution to Question 49.
Execute: Determine geometry and polarity of Cl3CH and CH3CH2–O–CH2CH3:
The molecules are both polar. So they can all interact with each other with dipole-dipole forces.
89. Result: C6H5N is polar, so it can interact with water using dipole-dipole forces.
Analyze: Given names and chemical formulas of two compounds, explain why one is miscible in water and the
other is not.
Plan: Adapt the plans used in the solution to Question 49.
Execute: Determine geometry and polarity of C6H6 and C6H5N:
C6H5N is polar, so it can interact with water using dipole-dipole forces. C6H6 is nonpolar, so it can only
interact with water using London forces. This explains why C6H5N is completely miscible in water and C6H6
is only slightly soluble.
90. Result: Several correct answers exist for this question. These are examples:
(a) nitrogen (b) boron (c) phosphorus (d) iodine
Analyze: Given specific formulas with an unknown element, X, name a Group 1A-8A element that could be X.
Plan and Execute: Use the specific bonding patterns of periodic groups and the Lewis structures from other
Questions in Chapters 6 and 7 to identify examples.
The answers given here are not the only correct answers. They are only examples.
(a) XH3 would have a central atom with one lone pair of electrons if X is in Group 5A, such as: N, nitrogen.
(b) XCl3 would have no lone pairs on the central atom, if X is in Group 3A, such as: B, boron.
(c) XF5 would have no lone pairs on the central atom, if X is in Group 5A and period 3 or higher,
such as: P, phosphorus.
(d) XCl3 would have two lone pairs on the central atom, if X is in Group 7A and period 3 or higher,
such as: I, iodine.
91. Result: Several correct answers exist. These are examples:

(a) beryllium (b) oxygen (c) sulfur (d) carbon
Analyze: Given specific formulas with an unknown element, X, name a Group 1A-8A element that could be X.
Plan and Execute: Follow the plan from the solution to Question 90.
The answers given here are not the only correct answers. They are only examples.
(a) XCl2 would have a central atom with no lone pair of electrons if X is in Group 2A, such as: Be, beryllium.
(b) XH2 would have two lone pairs on the central atom if X is in Group 6A, such as: O, oxygen.
(c) XF4 would have one lone pair on the central atom if X is in Group 3A and period 3 or higher,
such as: S, sulfur.
(d) XCl4 would have no lone pairs on the central atom if X is in Group 4A, such as: C, carbon.
92. Result: Five; see diagram below with dotted lines ( • • • ) showing intermolecular interactions.
Analyze: Given a Lewis structure for a molecule, show how water interacts with it using hydrogen bonds.
Plan: Identify all the possible interactions between one of the lone pairs on an O atom and the H atom in an
O–H bond and draw a dotted line between them O–H • • • O .
Execute: Five water molecules could hydrogen bond to an acetic acid molecule: one to each of the four lone
pairs on O atoms in acetic acid and one to the H atom bonded to an O atom in acetic acid.
93. Result: Three; see diagram below with dotted lines ( • • • ) showing intermolecular interactions.
Analyze: Given a Lewis structure for a molecule, show how water interacts with it using hydrogen bonds.
Plan: Identify all the possible interactions between one of the lone pairs on an N or O atom and the H atom in
an O–H bond or a N–H bond and draw a dotted line between them O–H • • • O, N–H • • • O, or O–H • • • N
Execute: Three water molecules could hydrogen bond to an ethylamine molecule. One to the lone pair on the
N atom in ethylamine and one to each of the H atoms bonded to the N atom in ethylamine.
94. Result: Diagram (d)

Analyze: Given a list of examples, determine which correctly describes hydrogen bonding.
Plan: Hydrogen bonding is a noncovalent interaction between one of the lone pairs on an N, O, or F atom and
the H atom in an O–H bond, a N–H bond, or a F–H bond. Compare each example to these requirements. If any
of them are not met, the example is incorrect.
Execute:
(a) This is incorrect, because the H atoms are not bonded to highly electronegative atoms and H atoms would
not be attracted to each other, either.
(b) This is incorrect. The H atoms are both bonded to O atom (EN = 3.4), but the two partial-positive H atoms
will not be attracted to each other!
(c) This is incorrect. The H atom is bonded to an F atom. This is a covalent bond, not an example of the
noncovalent interactive force called hydrogen bonding.
(d) This is correct. The H atom is bonded to an O atom (EN = 3.4) and is hydrogen bonding to another O
atom.
The only answer that is correct is (d).
95. Result: Diagram (a)
Analyze: Given a list of examples, determine which correctly describes hydrogen bonding.
Plan: Adapt the plan from the solution to Question 94.
Execute:
(a) This is correct. The H atom is bonded to an O atom (EN = 3.4) and is hydrogen bonding to an N atom
(EN = 3.0).
(b) This is incorrect. The H atom is bonded an H atom. This is a covalent bond, not an example of the
noncovalent interactive force called hydrogen bonding.
(c) This is incorrect. The H atoms are bonded to O atom (EN = 3.4), but the two partial-positive H atoms will
not be attracted to each other!
(d) This is incorrect. The H atoms are bonded to highly electronegative atoms (ENF = 4.0 and ENN = 3.0), but
the partial-negative N atom will not be attracted to the partial-negative F atom!
The only answer that is correct is (a).
96. Result: ; electron-trio geometry and molecular geometry both are triangular planar; ;
electron-trio geometry is triangular planar; molecular geometry is angular (120°).

Analyze, Plan, and Execute: In this fictional universe, a nonet is nine electrons. We will assume that the
number of electrons in the atom called “O” in the other universe is still six, the number of electrons in the atom
called “H” is still one, and the number of electrons in the atom called “F” is still seven. The equivalent to our
VSEPR model is the VSTPR model (Valence Shell Electron Trio Repulsion Theory), where electron trios repel
each other. The 6 electrons in the O atom would need three more electrons to make a total of nine. That means
it would combine with three H atoms to make this molecule:
In this H3O molecule, the central atom has three bonded atoms and no lone trios. That would make it AX3E0
type. As a result, the electron-trio geometry and the molecular geometry would both be triangular planar.
The 7 electrons in the F atom would need two more electrons to make a total of nine. That means it would
combine with two H atoms to make this molecule:
In this H3F molecule, the central atom has two bonded atoms and one lone trio. That would make it AX2E1
type. As a result, the electron-trio geometry would be triangular planar and the molecular geometry would be
angular at somewhat less than 120° due to the electron trio repelling the bonding trios to a narrower angle.
More Challenging Questions

97. Result: See structure below
Analyze: Given the name and chemical formula for an organic compound and its dipole moment, determine the
structural formula of the compound.
Plan:
Using the compound’s name and the discussion of constitutional isomers of aromatic compounds in Section 6-
11a, to assist in designing the dichlorobenzene structure. Use the solution to Question 7 to assist in locating the
positions of the Cl atoms in the nonpolar structure.
Execute: The para-isomer of dichlorobenzene will be nonpolar, since the polar bonds C–Cl are directly
opposite each other in this structure:
98. Result: (a) See diagrams below (b) (i) < (ii) < (iii)
Analyze: Given the chemical formula for an organic compound and some information about its structure,
determine the structural formula of the compound and rank order their melting points.
Plan:
Using the compound’s name and the discussion of constitutional isomers of aromatic compounds in Section 6-
11a, to assist in designing the Lewis structure and locating the ortho-, meta-, and para- positions of the –OH
groups in isomers.
Adapt the plans from the solutions of Questions 49 and 53 to help decide the order for the melting points.
Execute:
(a) The Lewis structures for the three isomers of C6H6O2 (each with one benzene ring and two –OH groups
attached) look like this:
(b) All of these molecules have the same kind and strength of hydrogen bonding; however, because of the
proximity of the two –OH groups in structure (i), these molecules are able to experience intramolecular
hydrogen bonding:
Less disruption of hydrogen bonding will be experienced when the (i) molecules undergo a transition to the
liquid state; hence, (i) will melt at a lower temperature than the other two.
The asymmetry of structure (ii) might suggest that the intermolecular forces could be somewhat weaker in
the solid, compared to those experienced among the higher-symmetry molecules in structure (iii).
Therefore, the predicted order for the melting points of these three solids would be (i) < (ii) < (iii).
99. Result: (a) see structure below (b) polar, asymmetric with polar bonds (c) cannot interact via hydrogen
bonding, since H is bonded to C and the bond is not polar enough to allow for H-bonding.
Analyze: Given the condensed structural formula for a compound, write a Lewis structure, explain the
molecule’s polarity, and explain whether it can interact using hydrogen bonds or not.
Plan and Execute:
(a) The “-ane” ending in the compound’s name suggests a two-carbon chain.
The formula, CHBrCl–CF3, suggests that the first C atom has an H atom, Br atom, and Cl atom bonded
to it. And, the second C atom has three F atoms bonded to it, as shown in the following Lewis structure
with 44 e–.
(b) While the Br–C, Cl–C, and C–H bonds are not very polar, the C–F bonds are much more polar. As an
asymmetric molecule with polar bonds, halothane is a polar structure.
(c) No, halothane molecules cannot interact with each other via hydrogen bonding, since the only H atom in
the molecule is bonded to a C atom and the C–H bond is not polar enough for the H to have a high
enough partial positive charge to do hydrogen bonding.
100. Result: (a) see structure below (b) First C: triangular planar, H–C–C and H–C–H bond angles are
120°; Second C: linear, C–C–O bond angle is 180° (c) First C: sp2-hybridized; Second C: sp-
hybridized; O: sp2-hybridized (d) polar, because the polar C=O bond contributes to a nonzero dipole
moment.
Analyze: Given the chemical formula and some information about the molecular structure, write the Lewis
structure, identify geometries, bond angles, hybridization of several atoms and explain polarity.
Plan: Adapt the solutions to Questions 32 and 43.
Execute:
(a) Ketene, C2H2O (16 e–) has no –OH bond, so it must have the following Lewis structure.
(b) 1st C atom: Its type is AX3E0, so the electron-region geometry is triangular planar with H–C–C and H–
C–H bond angles of 120°.
2nd C atom: Its type is AX2E0, so the electron-region geometry is linear with a C–C–O bond angle of
180°.
(c) Look at the 1st C atom: Its type is AX3E0, so the C atom must be sp2-hybridized.
Look at the 2nd C atom: Its type is AX2E0, so the C atom must be sp-hybridized.
Look at the O atom: Its type is type AX1E2, so the O atom must be sp2-hybridized.
(d) The C=O bond in this asymmetric molecule is a significantly polar bond which makes the molecule
polar.
101. Result: (a) see structure below (b) C in the CH2 groups are sp3-hybridized; C bonded to O is sp2-
hybridized (c) Yes, hydrogen bonding is possible in GHB (see diagram below) (d) All C atoms are
involved in sigma bonds; the right-most C atom is involved in one pi bond (e) All O atoms are
involved in sigma bonds; the double-bonded O atom is involved in one pi bond. (see diagram below)
Analyze: Given the condensed molecular formula for a compound, write the Lewis structure, identify
geometries, hybridization of several atoms, and sigma and pi bonds.
Execute:
(a) HO(CH2)3COOH (42 e–) has the following Lewis structure.
(b) Look at the C atoms in the CH2 groups: They are each of type AX4E0, so each of the three C atoms must
be sp3-hybridized.
Look at the right-most C atom: It is of type AX3E0, so the C atom must be sp2-hybridized.
(c) Yes, hydrogen bonding is possible in GHB. Two different H atoms and three different O atoms can
contribute to six different hydrogen bonding interactions. One of each of these six is show below.
Answers may vary in appearance, but should show the six different ways these atoms can interact:
The H on the –OH group can hydrogen bond to one of three O atoms (shown here, labeled 1, 2, 3).
The H atom on the COOH group can hydrogen bond to one of three O atom (shown here, labeled 4, 5, 6).
To determine the answers to (d) and (e), recall that every single bond is a sigma-bond. Every double
bond is one sigma bond and one pi bond. So the sigma and pi bonds in this molecule are shown here:
(d) All of the C atoms in the molecule are involved in sigma bonds. The right-most C atom is involved in
one pi bond.
(e) All of the O atoms in the molecule are involved in sigma bonds. The double bonded O atom is involved
in one pi bond.
102. Result: (a) see diagrams below (b) sp; sp; sp2 (c) sp2, sp2, sp3 (d) hydrogen azide: 3 σ bonds,
cyclotriazene: 4 σ bonds (e) hydrogen azide: 2 π bonds; cyclotriazene: 1 π bond (f) hydrogen azide:
180°; cyclotriazene: 60°
Analyze: Given the names and chemical formulas of two compounds, write their Lewis structures, identify the
hybridization of several atoms, the sigma and pi bonds and some bond angles.
Execute:
(a) The name “azide” suggests three N’s bonded together. The prefixes “cyclo” and “tri” suggests a three-
nitrogen ring. Therefore, the two isomers of N3H (16 e–) have the following Lewis structures:
hydrogen azide cyclotriazene

(b) Look at the 1st N atom (the left-most one) in hydrogen azide: It is of type AX1E1, so this N must be sp-
hybridized.
Look at the 2nd N atom in hydrogen azide: It is of type AX2E0, so this N is sp-hybridized.
Look at the 3rd N atom in hydrogen azide: It is of type AX2E2, so we’d think that the N is sp3-
hybridized. However, to accommodate the other resonance structure (shown in (c) with two double
bonds between the N atoms), one p-orbital must remain unhybridized, so the N is sp2-hybridized
(c) Look at the first two N atom (the two on right-side of the triangle) in cyclotriazene: Each N is of type
AX2E1, so each N atom must be sp2-hybridized.
Look at the 3rd N atom in cyclotriazene: It is of type AX3E1, so this N is sp3-hybridized.
For answering questions (d) and (e), recall that every single bond is a sigma-bond; every double bond is one
sigma bond and one pi bond. So the sigma and pi bonds in this molecule are shown here:
(d) In hydrogen azide, there are three sigma bonds. In cyclotriazene, there are four sigma bonds.
(e) In hydrogen azide, there are two pi bonds. In cyclotriazene, there is one pi bond.
(f) In hydrogen azide, the second N dictates the N–N–N bond angle. In (b), we ascertained that this N atom
is sp-hybridized, so the bond angle must be 180°.
In cyclotriazene, the VSEPR method of this chapter indicate that the N=N–N bond angles should be 120°
and the N–N–N angle should be 109.5°; however, because the three N atoms form a triangle, geometric
constraints dictate that these bond angles must be approximately 60°.
103. Result: (a) see diagram below (b) sp (c) sp2 (d) N≡N (e) 120° (f) 180° (g) 4 σ bonds and 3 π bonds
Analyze: Given the name and chemical formula of a compound, write the Lewis structure, identify the
hybridization of several atoms, the sigma and pi bonds and some bond angles.
Plan: Adapt the plans from the solutions of Questions 32 and 43.
Execute:
(a) Nitrosyl azide, N4O (26 e–) has the following Lewis structure.
(b) Look at the “terminal” N atom (the left-most one): It is of type AX1E1, so this N atom must be sp-
hybridized.
(c) Look at the “central” N atom (the third one from the left; the third of five atoms): It is of type AX2E1, so
it must be sp2-hybridized.
(d) The shortest bond between two atoms of given type is a triple bond. So, in nitrosyl azide, the shortest
nitrogen-nitrogen bond is the N≡N bond.
(e) To determine the N–N–N angle starting with the N atom bonded to the O atom, we have to look at the
third N atom from the left. As identified in (c), this atom is of type AX2E1, so it must have triangular
planar electron geometry, and the bond angle is approximately 120°.
(f) To determine the N–N–N angle using the N atoms not bonded to the O atom, we have to look at the
second N atom from the left. This atom is of type AX2E0, so it must have linear electron geometry, and
the bond angle is 180°.
(g) Every single bond is a sigma bond, every double bond is one sigma bond and one pi bond. Every triple
bond is one sigma bond, and two pi bonds. In this molecule, therefore, we have:
So, there are four sigma bonds and three pi bonds.

104. Result: (a) Angle 1: 120°, Angle 2: 120°, Angle 3: 109.5° (b) sp3 (c) single-bonded O: sp3, double-
bonded O: sp2
Analyze: Given the Lewis structure, identify some bond angles and the hybridization of several atoms.
Plan: Adapt the plans from the solutions of Questions 32-35.
Execute:
(a) For the N–C–O Angle 1: Look at the C atom: Its type is AX3E0, so it must have triangular planar
electron geometry, and the bond angle is approximately 120°.
For the C–C–C Angle 2: Look at the second of the three C atoms: Its type is type AX3E0, so it must have
triangular planar electron geometry, and the bond angle is approximately 120°.
For the O–C–O Angle 3: Look at the C atom: Its type is type AX4E0, so it must have tetrahedral electron
geometry, and the bond angle is approximately 109.5°.
(b) The N atom is of type AX3E1, so it must be sp3-hybridized.
(c) Look at each of the two O atoms with two single bonds: They both have type AX2E2, so they must each
be sp3-hybridized.
Look at the double bonded O atom: Its type is AX1E2, so it must be sp2-hybridized.
105. Result: (a) see structures below (b) see structures below
Analyze: Given the chemical formula of three compounds, write their Lewis structures and indentify
structural isomers.
Plan: Adapt the plans from the solutions of Questions 32-35. Use the cis- and trans- terms to differentiate
the two geometric isomers (as described in Section 6-5a).
Execute:
(a) Write three Lewis structures for N2H2 compound, using 12 electrons.
(b) The second and third structures are geometric isomers. The cis- structure has the H atoms on the same
side of the double bond. The trans- structure has the H atoms on opposite sides of the double bond:
H
..
H H
..N N
..N ..N H
cis- trans-
106. Result: (a) see structures below (b) 120°, 60°
Analyze: Given the names and chemical formulas of two compounds, write their Lewis structures and
identifysome bond angles.
Plan: Adapt the plan from the solutions to Questions 32-35.
Execute:
(a) The root- “az” means three N atoms bonded together. The suffix “ene” means double bond, so use this to
help write two Lewis structures for N3H3 compound with 18 electrons:
Triazene Triaziridine
(b) The central N atom in the N-N-N bond of triazene is of type AX2E1, so its bond angle is approximately
120°. The N atoms in triaziridine form a three-membered ring, so they are geometrically constrained to
has a 60° angle, and not the VSEPR predicted bond angles.
107. Result: (a) –81 kJ/mol; exothermic reaction (b) C atoms in all the methyl groups (H3C– and –CH3)
have electron-pair and molecular geometries are tetrahedral; the second and fourth carbons (counting
from the left) in both forms have electron-pair and molecular geometries of triangular planar; the
third carbon (from the left) in the enol form has electron-pair and molecular geometries of triangular
planar, in the keto form it has electron-pair and molecular geometries of tetrahedral; (c) 6.79 g CrCl3
and 12.9 g HC5O2H7
Analyze: Given the Lewis structures for a reactant and a product, calculate the reaction enthalpy and
determine whether it is exothermic or endothermic. Determine the electron-region and molecular geometries
around each C atom and specify changes. Given a mass of a compound and a balanced equation for the
synthesis, determine the masses of reactants needed.
Plan: Use the plans from Questions 6.34, 7.32, 3.63
(a) We break the bonds and form the bonds using bond enthalpies, as was done in Chapter 6 Question 6.34.
Here, we focus on the bonds that are changed during the conversion of the enol form to the keto form:
None of the other bonds change. We must break and form these bonds:
ΔrH = Σ Dbroken bonds – Σ Dformed bonds
ΔH = 1 × DO–H + 1 × DC–O + 1 × DC=C – (1 × DC=O + 1 × DC–C + 1 × DC–H)
Look up the bond enthalpies in Table 6.2.

ΔrH = 1 × (463 kJ/mol) + 1 × (351 kJ/mol) + 1 × (611 kJ/mol)
– [1 × (745 kJ/mol) + 1 × (347 kJ/mol) +1 × (414 kJ/mol)]

ΔrH = –81 kJ/mol exothermic reaction
(b) The methyl C atoms (CH3) in both forms are the same. The electron-pair and molecular geometries
about those C atoms are tetrahedral. The fourth C atom in both molecules is the same. They each have
three bonded atoms and no lone pairs, so the electron-pair and molecular geometries are both triangular
planar.
The left-most carbons shown in the enol and keto forms in (a) above have the same geometries. These C
atoms have three bonded atoms and no lone pairs so the electron-pair and molecular geometries are both
triangular planar.
The right-most carbons shown in the enol and keto forms in (a) above have different geometries. Look
first at the enol form: The right-most C atom has three bonded atoms and no lone pairs so the electron-
pair and molecular geometries are both triangular planar. Now look at the keto form: The right-most C
atom has four bonded atoms and no lone pairs, so the electron-pair and molecular geometries about that
C atom is tetrahedral.
When there is a shift from the enol to the keto form, one of the chain carbons shifts from triangular planar
to tetrahedral. That means the bond angle will narrow and the molecule will pucker more than it did
before.
(c) Adapt methods described in Chapter 3, such as given in the solution to Question 3.63.
Cr(acac)3 is Cr(C5O2H7)3, with a calculated molar mass of:
51.9961 g Cr + 3 [5 (12.0107 g C) + 2 (15.9994 g O) + 7 (1.0079g H)] = 349.9189 g/mol

The reactants are CrCl3 and HC5O2H7, with calculated molar masses:
51.9961 g Cr + 3 (35.453 g Cl) = 158.355

5 (12.0107 g C) + 2 (15.9994 g O) + 8 (1.0079g H) = 100.1076 g/mol
Calculate the number of moles of product:
1 mol Cr(acac)3
15.0 g Cr(acac)3 × = 0.0429 mol Cr(acac)3
349.9189 g Cr(acac)3
The balanced equation says: 1 mol Cr(acac)3 requires 1 mole of CrCl3.
€ 1 mol CrCl3 158.355 g CrCl3

0.0429 mol Cr(acac)3 × × = 6.79 g CrCl3
1 mol Cr(acac)3 1 mol CrCl3
The balanced equation says: 1 mol Cr(acac)3 requires 3 mol HC5O2H7.
€ 3 mol HC5O2 H 7 100.1076 g HC5O2 H 7

0.0429 mol Cr(acac)3 × × = 12.9 g HC5O2H7
1 mol Cr(acac)3 1 mol HC5O2 H 7
Assuming the reaction has a 100% yield, we need 6.79 grams of CrCl3 and 12.9 grams of HC5O2H7, .
108. Result: 3 2 2
€ (a) sp (b) sp (c) sp (d) Eight σ-bonds and two π-bonds (e) See structure below (f) See
structure below.
Analyze: Given the Lewis structure for a compound, identify hybridization of several atoms, and sigma and pi
bonds, and write one other resonance structure.
Execute:
(a) Looking at the structure, the single-bonded N atoms have type AX2E2,
so the N atoms must be sp3-hybridized.
(b) Looking at the structure, the double-bonded S atoms have type AX2E1,
so the S atoms must be sp2-hybridized.
(c) Looking at the structure, the double-bonded N atoms have type AX2E1,
so the N atoms must be sp2-hybridized.
(d) Each single bond is one σ-bond. Each double bond is one π-bond and one σ-bond.
The molecule has eight σ-bonds and two π-bonds.

(e) See structure drawn in (d).
(f) As described in Section 7-2c, Make a new double bond with one electron pair on a single-bonded N atom
with a double bonded S atom and move one pair of the original double bond electrons to a lone pair on
the next N atom in the chain, as shown here on the left side of the structure.
109. Result: NH3 and N(CH3)3 have sp3 hybridization. The bulky lone pair in NH3 is bulky enough to
narrow the bond angle slightly. The bulkier CH3 group does not permit the narrow angle. The
structures of N(SiH3)3 and N(GeH3)3 are sp2 hybridized, forming expanded octets on the outer atoms
from Periods 3 and 4.
Analyze: Given condensed structural formulas for several compounds, explain the trends in their bond angles.
Plan: Adapt the solutions to Questions 32-35.
Execute: As described in Section 7-2c, the smaller experimentally determined bond angle in NH3 is
attributed to the bulkier lone pair forcing the bonding pairs closer together, thereby reducing the H–N–H
bond angle from 109.5° to 107.5°.
When the H atoms are replaced with bulkier –CH3 groups, the repulsion of the methyl H atoms prevents the
reduction of the C–N–C bond angles. In fact, the experimental angle is slightly wider 110.9° than predicted
by VSEPR (109.5°).
To accommodate larger Si and Ge atoms, even wider bond angles are required. The experimental angle is
120°, which is the angle predicted by VSEPR (109.5°) for sp2-hybridization. Hence, it appears that the lone
pair may no longer be in a hybrid orbital, but in an unhybridized p orbital:
Because Si and Ge are in the third and fourth period, they can have an expanded octet. That means three
more valid resonance structures can help to stabilize an unhybridized lone pair.
These structures show the N atom with the type AX3E0, consistent with the experimental 120° bond angles.
110. Result: See structures below

Analyze: Given a Lewis structure for a molecule, show how hydrogen bonds explain two different solid
structures.
Plan: Identify all the possible orientations for interactions between one of the lone pairs on an O atom and
the H atom in an O–H bond and draw a dotted line between them O–H • • • O .
Execute: The H atom will make the strongest hydrogen bonds with the double bonded O. If those C=O
bonds are on the same side of the C–C bond, we get the zig-zag chain:
The long linear chain would form when the C=O bonds are on opposite sides of the C–C bond.
111. Result/Explanation
(a) As shown in the Tools of Chemistry Infrared Spectroscopy in Section 7-2d, the motion of atoms include
stretching and bending. The three atoms can stretch in sync, where both the bond and the hydrogen bond
get longer (and shorter) together:
The H atom, between the other two, does not move very much in this stretching motion.
The three atoms can stretch in alternating pattern, where the bond gets shorter when the hydrogen bond
gets longer (and vice versa):
The H atom moves more in this stretching motion.

The three atoms can also perform a bending motion:
The H atom does move significantly more in this vibration, since it has the lowest mass.
(b) The substitution of the H atom with a D atom will lower the frequency of the vibrations. It would affect
the bending vibration the most and the asymmetric stretching vibration more than the symmetric
stretching vibration, since the H atom moves more in those two vibrations.
Conceptual Challenge Problems

Many of the Conceptual Challenge Problems in this book go beyond the topic in the chapter, and can help to stretch
and integrate students’ understanding of how the subjects in various chapters interconnect. Many of them are open-
ended and philosophical and as such can be used for group work, special projects, or class discussions. It is not
always possible to provide a complete “solution” for some of these questions; however, some additional information
and helpful instruction is provided for the use and evaluation of each question.
CP7.A VSEPR theory helps predict the particular geometric shape of a combination of covalently bonded atoms.
Lewis structures only reliably predict the atom connectivity and the type of bonding (single, double,
triple bonds) in a covalent structure. Combining the VSEPR model with Lewis structure refines a
prediction of the molecules shape.
CP7.B Several answers exist for this problem, depending on how the students interpret the word “evidence.”
Experiments can show that molecules like HCN, CO2, and H2Be are all linear, even though they have a
variety of single, double and triple bonds. The experimental evidence is usually spectroscopic. You will
need to decide to what extent you wish to go beyond the scope of this course to describe specific types of
evidence identifying a molecule as linear in shape.
CP7.C A theoretical argument could be made showing that the overlap between two orbitals does not diminish
during the rotation of a sigma bond; however, rotating about a double bond does interfere with the
necessary requirement that p-orbitals on the adjacent atoms are parallel to have maximum overlap.
During the twisting process, the π bond must be broken at the point where the p-orbital on one atom is
perpendicular to the p-orbital on the other atom. Experimental evidence can be discussed as well,
including the fact that only double-bonded molecules have cis- and trans- isomers. Experimentally, they
can be proven to have the same formula and the same connectivity; however, their physical properties are
measurably different.
CP7.D VSEPR theory is empirically derived using the concept of simple electron repulsion (due to Coulomb’s
Law) and geometry to explain the relative orientations atoms and electrons will take when bonding to
form a molecule. Hybrid orbital theory is more closely related to quantum theory because it identifies
combinations of atomic orbitals (the Hamiltonian wave functions) and overlaps the orbitals to make the
new molecular orbitals for the bonding electrons. Both theories predict approximately correct molecular
shapes and bond angles. Neither theory accurately accounts for geometric adjustments caused by bulky
components, such as lone pairs, large atoms (see Question 109), or small rings (see Questions 73, 102,
and 106).
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Chemistry The Molecular Science 5th

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Chapter 7: Molecular Structures

Suggestions for Effective Learning

Cooperative Learning Activities

End-of-Chapter Solutions for Chapter 7

Analyze, Plan, and Execute:

The formula is C14H18O5N2.

(e) and are both AX3E1, so the electron-region geometry is tetrahedral.

The four bonds need sp3-hybridization on the C atoms.

Questions for Review and Thought

(c) AX3E1 type has triangular pyramidal molecular geometry.

(d) AX4E0 type has tetrahedral molecular geometry.

(b) CH2Cl2 (20 e–) The type is AX4E0, so it is tetrahedral.

(c) BH3 (6 e–) The type is AX3E0, so it is triangular planar.

(d) SeCl6 (48 e–) The type is AX6E0, so it is octahedral.

(e) PF3 (26 e–) The type is AX3E1, so it is triangular pyramidal.

Analysis: Explain why one ion is bent and one is not.

25. Result: (a) Twelve at 90° (b) 180° (c) 180°

26. Result: NO2+

Chirality in Organic Compounds (Section 7-2)

Hybridization (Section 7-3, 7-4)

The S atom must be sp3-hybridized.

The C atom must be sp-hybridized.

(b) The shortest carbon-to-carbon bond is the triple bond, C3 C4. ≡

40. Result: see structures with σ and π bonds designated below

Molecular Polarity (Section 7-5)

ΔENB–H = ENH – ENB = 2.1 – 1.9 = 0.2

ΔENB–F = ENF – ENB = 4.0 – 1.9 = 2.1

ΔENC–H = ENC – ENH = 2.4 – 2.1 = 0.3

ΔENC–Cl = ENCl – ENC = 2.7 – 2.4 = 0.3

ΔENBr–F = ENF – ENBr = 4.0 – 2.6 = 1.4

ΔENBr–Cl = ENCl – ENBr = 2.7 – 2.6 = 0.1

ΔENO–H = ENO – ENH = 3.4 – 2.1 = 1.3

ΔENS–H = ENS – ENH = 2.3 – 2.1 = 0.2

ΔENN–H = ENN – ENH = 3.0 – 2.1 = 0.9

ΔENN–O = ENO – ENN = 3.4 – 3.0 = 0.4

(b) The Lewis structure/geometry has polar S–Cl bonds.

ΔENN–O = ENO – ENN = 3.4 – 3.0 = 0.4

(b) The Lewis structure/geometry has polar F–S bonds:

Noncovalent Interactions (Section 7-6)

54. Result: See structures below

(a) (b) (c) (d)

Biomolecules (Section 7-7)

61. Answer/Explanation: The structure of a section of DNA with T-C-G

Molecular Structure Determination by Spectroscopy

(b) The most polar bond is the C≡N bond.

A (10 e–) B (26 e–) C (8 e– and 26e–)

D (8 e–) E (16 e–) F (14 e–)

G (8 e– and 14 e–) H (8 e–) I (20 e–)

A (8 e–) B (26 e–) C (40 e–)