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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
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CHAPTER VII.
A STRANGE FANCY.
“What was that?” asked Mabin with a shiver.

She and Rudolph had both turned instinctively toward the spot
from which the rustling noise had come.
“A cat, most likely,” answered Rudolph.
But Mabin shook her head.
“I saw something,” whispered she. “It was not a cat, it was not an
animal at all; it was a man.”
Perhaps Rudolph had his suspicions, for he expressed no
surprise. Before he could answer her they heard the crackling and
rustling again, but at a little distance. The intruder was making his
way through the shrubbery.
“Won’t you find out who it is?” whispered the girl again.
Rudolph hesitated.
“Perhaps I know,” said he shortly. “But if you wish, of course I can
make sure.”
Then, with evident reluctance, and taking no pains to go
noiselessly, he followed the intruder through the bushes, and was in
time to catch a glimpse of him as he disappeared over a part of the
fence that was in a broken-down condition. Rudolph did not attempt
to continue his pursuit, but contented himself with waiting until he
heard the side gate in the garden wall of “Stone House” swing back
into its place with a loud creaking noise. Then he went back to
Mabin. She was standing where he had left her, on the broad gravel
path under the faded laburnum. The shadows were very deep under
the trees by this time, and in the half-light her young face, with its
small, delicate features, its dreamy, thoughtful eyes, full of the
wonder at the world of the very young, looked so pretty that for the
moment Rudolph forgot the errand on which he had been sent, and
approached her with no thought of anything but the beauty and the
sweetness of her face.
She, all unconscious of this, woke him into recollection with one
abrupt word: “Well?”
“Oh!” almost stammered he, “it was as I thought, the same person
that I saw watching before.”
“And he went into our garden. I heard the gate,” said Mabin with
excitement. “It must be this Mr. Banks. Oh, who do you think he is?
What do you think he has come for?”
Rudolph was silent. Even to the least curious mind the
circumstances surrounding both him and Mrs. Dale could not seem
other than mysterious. If he were a detective, and he certainly did
not look like one, surely he would not go to work in this extravagant
manner, by renting a large and expensive house merely for the
purpose of watching his next-door neighbor. Neither, it might be
supposed, would he set to work in such a clumsy fashion as to be
caught making his investigations at the very outset. Rudolph felt that
the whole affair was a mystery to which he could not pretend to have
the shadow of a clew. He confessed this to Mabin.
“I wish,” he went on, in a gentle tone, “that I had known something
of this before your father went away.”
“Why?” asked Mabin in surprise, and with something like revolt in
her tone.
“Because I should have told him something, just enough at any
rate to have made him take you away with him.”
Mabin was for a moment dumb with surprise.
“What,” she stammered at last, “after all your talk about my being
right to stand by my friend?”
“Even after all that,” assented Rudolph with decision. “The matter
is getting too serious,” he went on gravely. “I am afraid myself of
what may be going to happen.”
“Then,” retorted the girl, “for all your talk about meanness being
excusable in a girl, I can be a better friend than you.”
Rudolph smiled.
“Ah,” said he, “you forget that with you it is only a question of your
friendship for Mrs. Dale. Now I have to think of both of you.”
“You need not trouble yourself about me, I assure you.”
“But that is just what I must do, madam, even at the risk of your
eternal displeasure,” said Rudolph, with a mock-heroic air which
concealed real anxiety. “You are not only daring enough, you are too
daring where your heart is concerned, and it is the business of your
friends to see that you do not suffer for your generosity.” He spoke
with so much quiet decision that Mabin was impressed and rather
frightened, and it was with a sudden drop from haughtiness to
meekness that she then asked:
“What are you going to do, then?”
Rudolph hesitated.
“What I should like to do,” said he, “is to take you to my mother’s
——”
Mabin almost screamed.
“You won’t do that,” she said quietly, with her lips very tightly
closed.
“She would be very kind to you,” suggested Rudolph gently,
pleadingly.
He knew the prospect was not an enticing one, but he was not so
quick as the girl to see all its disadvantages.
“And don’t you see that it would set them all saying the most
dreadful things about poor Mrs. Dale, if I were to leave her suddenly
like that? I shouldn’t think of such a thing. It would be cruel as well as
cowardly. She would never be able to stay in Stone after that.”
“I don’t think she will be able to stay in any case,” said Rudolph
gloomily. “If she is persecuted by this spy on the one hand, and by
the old woman on the other, it isn’t likely that she will be able to stay
here long.”
A new idea flashed suddenly into Mabin’s mind and then quickly
found expression:
“Do you suppose,” she asked, “that this man, this Mr. Banks, is
paid by the old lady to spy upon Mrs. Dale? The old lady must be
very rich, I think, and she is eccentric evidently.”
But Rudolph was inclined to think this idea far-fetched. From what
he had seen of the mysterious spy he had come to quite another
conclusion, one that at present he did not care to communicate to
Mabin, for fear of alarming her unnecessarily.
“Of course it is possible that the man may be a paid detective,”
admitted he doubtfully, “but there was nothing of the cut of the ex-
detective about your Mr. Banks. And now,” went on Rudolph, who
found Mabin herself a more interesting mystery than the unknown
man, “let us forget all about him for a little while, and go up to the old
seat where the trees leave off, before it gets too dark for us to see
the sea. You remember the old seat, and how we used to trespass to
get at it, don’t you?”
Mabin blushed a little. She remembered the old seat very well; an
old broken-down bench supported on the stumps of a couple of
felled trees, just on the edge of the plantation belonging to “The
Towers.” Being conveniently near both to “Stone House” and the
Vicarage, the children of both houses had established, in those far-
off years which Rudolph was recalling, a right to tread down the old
fence at that particular point, and to hold wonderful picnics of
butterscotch and sour apples.
“We won’t go up there now,” she said, with a sudden demureness
which contrasted strongly with the eagerness she had shown while
discussing the persecution of Mrs. Dale. “It’s getting dark, and rather
cold, I think, and besides, I hope by this time that Mrs. Dale may be
ready to see us again.”
Rudolph felt snubbed. The girl’s manner was so precise, so stiff,
that it was impossible for him to understand that her sudden
primness was only a relapse into her ferocious girlish modesty. He
followed her without a word toward the house, and there just inside
the portico they saw the slight figure in black looking like a pathetic
vision in the gloaming, with its white, tear-stained face and slender
little jewelled hands.
“Well?” said Mrs. Dale. And her voice was hoarse and broken. “I
have been waiting here for you, wondering where you had gone. I
had almost begun to think,” she went on, with assumed playfulness,
which did not hide the fact that her fear had been real, “that you had
run away from me altogether.”
Mabin lost her awkwardness, her stiffness, her shy, girlish reserve
in an instant; moved by strong pity and affection, she took the two
steps which brought her under the portico, and stooping, flung her
arms round the little figure.
“You didn’t—really?” she whispered hoarsely. “Oh, I hope not, I
hope not!”
Mrs. Dale could not answer. But Mabin felt her frame quiver from
head to foot, and heard the sound of a stifled sob. Rudolph stepped
noiselessly out into the garden again.
“My dear, my dear child,” murmured Mrs. Dale, when she had
recovered some of her self-possession by a strong effort, “you would
have been quite justified if you had gone. But I am glad, oh, so glad,
that you have waited for me to drive you away.”
“You won’t do that!” cried Mabin, starting back, and seeing with
surprise in the fair, blue-eyed face an expression of strong
resolution. “After pretending you were so glad to have me!”
“It was no pretence, believe me!” said Mrs. Dale with a sad little
smile. “But I have got to send you away all the same. It would not be
right to keep you here, now that I see the persecution I am to be
subjected to still.” And her blue eyes flashed angrily as she spoke.
But the next moment her face changed again, and she added
quickly, “I have deserved it all. More than all. I am not complaining of
that; I have no right to complain. Only—she might have spared you. I
should have done you no harm; you would have learnt no evil from
me, wicked as I am.”
The girl interrupted her, with a frightened face, and speaking in an
eager whisper:
“Oh, hush, hush! You are not wicked. It is dreadful to hear you say
such things! I will not let you say them. You have the kindest heart in
the world; if you have ever done wrong, you are sorry, bitterly sorry.
Wicked people are never sorry. Let me stay with you and comfort
you if I can, by showing you how happy it makes me to be with you!”
Mrs. Dale shook her head. She did not, however, repeat in words
her resolve that Mabin must go, though the girl guessed by the
expression of her face that her mind was made up on the subject.
They stood silently looking out at the soft beauties of the twilight,
the greens as they melted into grays blending in such a tender
harmony of color that the sight seemed to supply a balm, through
tear-dimmed eyes, to their heavy hearts; the scent of the roses came
to them across the broad space of gravel, too, mingled with the
pleasantly acrid perfume of the limes.
Rudolph’s step, as he took advantage of the silence to thrust
himself again upon the notice of the ladies, startled them both.
“Now you’ve spoilt it all!” cried Mrs. Dale, in a tone which was
meant to be one of light-hearted pleasantry, but which betrayed too
plainly the difficulty she had in assuming it. “The garden looked like a
fairy picture till you rushed in and ruined the perspective. Aren’t you
going to apologize?”
“No. The picture wanted human interest, so I painted myself into
the canvas, just to satisfy your artistic susceptibilities. I am sorry to
find you so ungrateful. I hope you, Mabin, have more appreciation?”
But the girl’s eyes were full of tears, and not being used to this
light strain of talk, she could not answer, except by a few mumbled
words which had neither sense nor coherence. Mrs. Dale put up her
hand—she had to stretch it up a long way—and smoothed the girl’s
pretty brown hair.
“Don’t tease her,” she said softly. “Mr. Bonnington, I mustn’t ask
you to dine with us, but I would if I might.”
“And why mustn’t you?” asked Rudolph.
“Well, because, in the miserably equivocal position I am in, it
would be a pleasure—if I may take it for granted that it would be a
pleasure to you, as it would certainly be to me—dearly bought. The
Vicar would strongly disapprove; your mother would be shocked
beyond measure.”
“But I shouldn’t mind that, I assure you. I’ve shocked my mother
and excited the disapproval of my father so often that they don’t
expect anything else from me. Besides, I am afraid you flatter
yourself too much in believing that you have such an enviable
peculiarity; if you were to issue invitations to the whole parish to a
garden party, or a dinner, or anything you liked, I’m afraid you would
be disappointed to find that everybody would come.”
“Perhaps they would think there was safety in numbers, and that,
fortified by the presence of everybody else, they could gaze at the
monster in security!” suggested Mrs. Dale with a smile.
“In the mean time how much nearer have I got to get to inviting
myself to dinner this evening?” said Rudolph, with a subdued voice
and a meek manner.
“Ah, well, for Mabin’s sake then, I spare you the humiliation and
invite you myself. You shall stay to amuse her, since I am afraid she
would find me a very dreary companion.”
“Indeed I shouldn’t,” cried Mabin, blushing deeply, and speaking
with as much energy as if the presence of Rudolph were an injury. “I
should like nothing better than an evening alone with you.”
Rudolph drew a deep sigh, and even Mrs. Dale could not suppress
a smile at the girl’s unconscious gaucherie. When Mabin realized
what a stupid thing she had said, she was of course too much
ashamed of herself to laugh at her clumsy words, and fell, instead,
into a stiff silence which the others found it impossible to make her
break except by demure monosyllabic answers.
When they went into the dining-room, therefore, the evening did
not promise to be a lively one. Mrs. Dale seemed to find it impossible
to shake off the effects of the visit of her persecutor. Rudolph was
oppressed by fears for both the ladies, and by doubts whether his
presence there was not an indiscretion which would make matters
worse for both of them. While Mabin, perplexed and troubled by a
score of unaccustomed sensations, was the most silent, the most
distressed of all.
Daylight was still streaming in from the West as they took their
seats at the table in the dingily furnished room. Mrs. Dale gave a
little shudder as she glanced from the “furnished house” knives to
the commonplace dinner service.
“Ah!” she said, “it is not like this that I used to entertain my friends.
My little dinners had quite a reputation—once!”
Then, as if she felt that these regrets were worse than vain, she
turned the subject abruptly, while a spasm of pain for the moment
convulsed her face.
Rudolph on his side was sorry she had mentioned the “little
dinners.” They suggested a past life in which there had been
something more than frivolity; something with which he would have
dissociated Mrs. Dale if he could. But innocent Mabin, wishing to say
something, brought the conversation back to the point it had left.
“But why can’t you have pretty dinners now, if you like to?”
Mrs. Dale’s fair face grew whiter as she answered gently:
“I will tell you—presently—some day—why I don’t have anything
pretty or nice about me now.”
And Mabin, feeling that she had touched a painful chord, became
more silent than ever.
Perhaps it was her sudden subsidence into absolute gloom which
caused the other two to make a great effort to restore something like
animation to the talk. And being both young, and of naturally high
spirits, they succeeded so well that before the meal which had begun
so solemnly was over, Mrs. Dale and Rudolph were talking and
laughing as if there had never been a shadow upon either of their
lives. At first they made brave attempts to drag Mabin into the
conversation. But as these efforts were in vain, it naturally ended in
her being left out of the gayety, and in her sitting entrenched in a
gloomy silence of her own.
And when dinner was over, and they all went into the little
adjoining room which Mrs. Dale called her “den,” it was quite natural
that Mrs. Dale should sit down at the piano, in the good-natured wish
to leave the young people to entertain each other; and equally
natural that Rudolph, on finding that Mabin had nothing to say to
him, and that she was particularly frigid in her manner, should go
over to the piano, and by coaxing Mrs. Dale to sing him his favorite
songs and then hers, should continue the brisk flirtation begun at the
dinner-table.
Mabin had brought it all upon herself, and she tried to persuade
herself that it was quite right and natural, and that she did not mind.
And when Rudolph was gone, and she was alone with her hostess,
she succeeded in persuading her that she had not felt neglected, but
had enjoyed the merriment she had refused to share.
But when she got upstairs into her pretty bedroom, after bidding
Mrs. Dale good-night, she had the greatest difficulty in keeping back
the tears which were dangerously near her proud eyes.
She did not care for Rudolph, of course not; she wanted him to fall
in love with Mrs. Dale, if indeed he had not already done so, and
marry her and console her for all her troubles, and stop the
persecution of “the cat.” But somehow this hope, this wish, did not
give her all the unselfish satisfaction it ought to have done.
And Mabin, wondering what had happened to take the prettiness
out of the room and the pleasure out of her acquaintance with Mrs.
Dale, fell asleep with her heart heavy and full of nameless grief.
She woke with a start to find a white figure standing motionless in
the middle of the room. Mabin sprang up in bed and rubbed her
eyes. Was she awake? Or was she only dreaming that the body of a
dead woman, stiff, rigid, but in an upright position, was standing like
a marble statue between the bed and the nearest window?
She leaped out of bed, and, not without uncanny fears, touched
the statuesque figure.
“Mrs. Dale!” she almost shrieked, as the great eyes suddenly
turned and fixed a blank, wild gaze upon her face. “Oh, what has
happened? What is the matter?”
The figure, which, in white night garments, had looked so unlike
the black-robed widow that she had not recognized it, trembled from
head to foot. The lips parted, but at first no word escaped them. At
last with a strong effort she uttered these words:
“Let me stay here. Let me sit in this arm-chair till morning. Oh, I
will not hurt you, or frighten you. But if I go back I shall go mad! This
house is haunted, haunted! I have seen——”
A hoarse rattle in her throat seized her, threatened to choke her.
With one wild glance round, peering into the corners of the room,
she flung herself on the floor, and buried her face in the chair.
CHAPTER VIII.
A HAUNTED HOUSE.
Mabin was taken so thoroughly by surprise, on seeing the wild

self-abandonment of her unhappy companion, that for a few minutes
she stood staring at the crouching figure on the floor like one only
half-awake.
Was this really Mrs. Dale, this haggard, panting creature with the
hoarse voice, the twitching hands, the wide eyes full of unspeakable
terror. Mabin’s sympathy was ready, but at first she did not dare to
offer it. Such terrible anguish, such paralyzing fear, as that from
which the miserable woman was suffering, was something surely
beyond her poor powers of comfort! And even as the girl advanced
timidly a step nearer to her grief-stricken friend, there flashed into
her mind the horrible question: What must this secret be which was
locked in the widow’s breast, that could throw her into such
paroxysms of abject terror? For, not unnaturally, Mabin came to the
conclusion that the vision which had alarmed Mrs. Dale was one of
the results of the remorse from which she owned that she was
suffering.
“Don’t! Don’t sob like that! You will make yourself ill; you will
indeed. There is nothing, there is nobody here to frighten you,” said
the girl at last, drawing a little closer to the crouching figure, but not
yet daring to touch her, or to speak in a tone louder than a whisper.
At the first sound of her voice, Mrs. Dale had started, and raised
her head quickly, turning to the girl’s view a face so much altered, so
drawn, so old-looking, that she hardly recognized the features of the
lovely widow. Then, when the voice ceased, she glanced round the
room again, with the same hunted, anxious look as before.
“Nothing—nobody to frighten me!” she repeated in a shaking
voice. “No, of course not, of course not. How silly I have been! I am
afraid I frightened you, dear,—with my dreams, my silly fancies!”
She struggled, as if worn out and exhausted by her emotion, to
gain her feet. Timidly, gently, Mabin helped her to rise.
“I’m very glad I was here,” answered Mabin, in kindly tones that
sent a shiver of grateful recognition through her agitated companion.
“Do you feel better now?”
“Yes, oh, yes, I am all right. I am not ill. I am so much ashamed of
myself for disturbing you. I don’t know how to apologize,” answered
Mrs. Dale, trying bravely to speak in her usual tone, but glancing at
the door and then back to the windows as she uttered the words: “It
must have been a dream, of course, that frightened me.”
And then, quite suddenly, she broke down again, and slipping from
the supporting arm of her young companion, she threw herself into
the wicker arm-chair, and burst into a passion of tears. Uncertain
what to do, Mabin, in her sympathy and kindness, did exactly the
right thing. She drew another chair besides the wicker one, sat down
in it, and putting her right arm round Mrs. Dale’s shoulder, and
holding the poor lady’s trembling fingers in her own, remained in
perfect silence until the first ebullition of violent grief had passed
away.
“I shall never forget your kindness, child, never,” said Mrs. Dale,
when, as suddenly as it had begun, her passion of tears ended. “You
have saved me from going mad—yes, mad. I—I must leave you now,
or you won’t get any rest.”
She rose as she spoke; but Mabin saw that the panic of terror
which had been upon her at her entrance was regaining its hold
upon her as she approached the door. With her fingers on the handle
she stopped, and seemed once more to grow rigid with fear.
Mabin was by her side in an instant.
“Stay here,” she said. “You will have the dream again perhaps, if
you go away by yourself.”
At these words a shiver ran through Mrs. Dale, and she faltered.
“It must have been that gloomy room!” she said at last in a
whisper. “And the effect of her visit! But it will kill me if it comes
again!” Suddenly she turned to Mabin. “May I lie on the sofa until the
morning?” she asked piteously. “I won’t disturb you. I feel as if I
should be safe from—it—in here with you?”
The wistful pleading in her eyes brought the tears to Mabin’s.
“Of course you must stay,” she cried heartily. “And I do hope you
will get to sleep, and not have any more dreams.”
Very quietly Mrs. Dale lay down on the couch between the
windows, and drawing the sofa blanket over her, and refusing any
other covering, she closed her eyes. Mabin knew that this apparent
tranquillity was assumed only, and she placed herself on the bed in
such a position that she could watch her friend, while appearing to
be herself asleep.
Before many minutes had passed, she saw, from between half-
closed eyelashes, that Mrs. Dale was sitting up, and bending her
head in a listening attitude. And presently the slender figure with its
white dressing-gown slipped softly off the sofa, and hurried on tiptoe
across the floor to the door. There it knelt down and listened again.
And after a few minutes Mrs. Dale turned the key in the lock and
crept back, not to the couch, but to the arm-chair.
Mabin shut her eyes and tried to disentangle the knot of strange
ideas that filled her brain:
What was the nature of the secret which weighed on the
conscience of Mrs. Dale? Why was she kept in luxury by the very
woman who tried to make her life unbearable, to cut her off from
every human friend? What was the strange tie between the hard,
elderly woman and the impulsive, volatile young one? What was the
vision which had caused her so much distress? And, above all, why,
if it was only a vision, did she try to keep it away by locking the door?
And why—and why—? More questions surged up into her tired
brain; but Mabin forgot them as they rose. She fell asleep.
When she awoke in the morning it was to find that some one was
knocking at the door, and then she heard the housemaid’s voice
announcing that it was eight o’clock. She sprang up, and looked
toward the sofa, but there was no one but herself in the room.
Surely, she thought, the strange visit of the night must have been
a dream? The rug on the sofa was neatly folded, just as it had been
when she came up to bed last night. Not a sign was to be seen of
any intrusion during the night.
Even when she went downstairs and met Mrs. Dale in the hall,
there was little to tell of the experience of the hours of darkness.
Perhaps the pretty widow looked a little paler than usual, but in every
other respect she was the same airy, impulsive creature, now
smiling, now looking sad, as she had been before the dreadful visit
of the lady whom irreverent Mabin called “the cat.”
It was not indeed until breakfast was over and they had gone out
into the garden to cut some flowers while the dew was on them, that
either of the ladies made any reference to the events of the night.
Mrs. Dale, with one daintily shod foot in a flower-bed, was
stretching out her hands toward a bush of sweet-peas, when, without
turning her head, she said:
“I am in great trouble about you, Mabin.”
“Are you? Why, Mrs. Dale?”
“I don’t quite know what to do with you. If I send you to Mrs.
Bonnington, I shall have to tell some shocking tarradiddle about the
drains having come up, or the roof having given way, and she will be
sure to find me out and to pry, and to give both of us what the old
women call ‘much unpleasantness.’ And if I send you on to Geneva,
I don’t know whether they will be glad to see you when you arrive.”
“And I’m sure they won’t,” said Mabin heartily. “And there is one
other objection to sending me anywhere, and that is that I won’t go.”
Mrs. Dale dropped her sweet-peas, and turned round. Her eyes
were full of sudden tears.
“Nonsense, child!” she said sharply, but in a querulous tone which
betrayed her emotion, “nonsense! It was decided yesterday
afternoon that you were to go. You know it was.”
“You decided that I was to go. I didn’t. And—” instinctively she
dropped her voice—“And something that happened last night—in the
night, made me decide not to go. There!”
“But, my dear——”
“No, Mrs. Dale, I’m not to be ‘got round.’ You’ve chosen to take me
upon your shoulders, so now you must just keep me. Ha, ha! You
didn’t know I had so much determination, did you?”
But Mrs. Dale could scarcely speak. Now for the first time that
morning Mabin realized that the scene of the night had really taken
place, for the emotion aroused by this little bit of talk had brought
back into Mrs. Dale’s blue eyes a faint reproduction of the wild terror
she had shown when she came to the girl’s room. When she had
recovered her voice, the lady in black, pale, hoarse, shaken with her
agitation, stammered out these words:
“My dear girl, it is beautiful of you to offer to stay. But I cannot let
you. You ought never to have come. I was mad, wicked to let you
come; and my madness and my wickedness I must bear alone.”
How strange these words seemed in the broad daylight, Mabin
thought! By the weak glimmer of the night-light Mrs. Dale’s wild looks
and words had seemed fantastic, weird. But the broad sunlight
seemed to give the nameless horror which hung about the poor little
lady in black a reality as vivid as it was painful. But with this feeling
there came also into the heart of the young girl a great tenderness
toward the suffering woman, who was haunted by the shadow of her
own past. So she smiled, and with a pretty, half-shy look in her eyes,
said:
“You told me I saved you from going mad. So I mean to stay. And I
mean to sleep in the same room with you, so that you shall not be
frightened any more.”
Mrs. Dale shook her head.
“I can’t let you do that,” said she. “I don’t sleep very well, and
sometimes I start up and cry out. I should frighten you.”
“Then we will exchange rooms,” said Mabin.
By the look of joy and relief which flashed over Mrs. Dale’s face at
this suggestion, Mabin saw that she had conquered.
“But—won’t you be afraid?” asked the widow in a troubled voice.
“What! Of a ghost, a vision? Or of having bad dreams? No, not a
bit.”
Mrs. Dale glanced gratefully at the young face, with its look of
robust Philistine scorn of phantoms.
“It is a temptation,” she murmured. “For, after all, I know, I know
that it was only a dream, a horrible dream. And there is no fear that
the dream will come to you.”
“And if it did,” retorted Mabin stoutly, “it wouldn’t frighten me. I’m
too ‘stodgy;’ I have no imagination.”
Mrs. Dale smiled sadly.
“You are right,” she said. “If you did have the same dream, it would
have no terrors for you. Your conscience is clear.”
“And my digestion good,” added Mabin lightly, as she picked up
the fallen flowers and put them in her basket.
There was no doubt that her refusal to go had taken a load of
melancholy from the shoulders of her hostess, who sent the young
girl out for a walk as soon as the gathering of the flowers was over,
and charged her not to go far enough to tire her still weak ankle.
Mabin, with a book and a sunshade, sauntered slowly down the
hill to the nearest gap in the cliff, and went down the steep descent
to the sands. This was no paradise of nursemaids and babies, but a
solitary nook beloved by quiet maiden ladies and sentimental
couples. With rash disregard of the danger of sitting under a chalk
cliff, Mabin found a seat on a rock worn smooth by the sea, opened
her book and began—not to read.
The circumstances to which she found herself were far too
interesting for her to be able to give herself up to the milder
excitements of fiction. She sat with her open book on her lap and her
eyes staring out at the sea, which was vividly blue in the strong
sunshine, when she became suddenly conscious of a footstep she
knew in her immediate neighborhood.
Although she affected to be surprised when Rudolph appeared
before her, she had known that he was approaching, and her heart
began to beat very fast. He looked down at her between the spikes
of her sunshade, pretending to be afraid to speak to her.
“Good-morning,” said she at last.
“I was wondering whether I dared say the same thing!”
“Dared?”
“Yes. After your treatment of me last night, I felt nervous.”
“My treatment of you! What treatment?”
“Why were you so unkind? Or mustn’t I ask why?”
“You may ask, of course. But I can’t give you any answer, because
I didn’t know that I was unkind.”
“I wish I could believe that.”
“Well, if you won’t believe it, I have nothing to say.”
Rudolph was silent a few minutes. Then with a burst of explosive
energy, he made up his mind.
“No!” he cried so loudly that Mabin started, and threw himself
down on the sand beside her, “I will not be daunted. I will encase
myself in double snub-proof armor plates, and I will try to teach her
that to be dignified it is not necessary to be unkind—and—yes, I will
say it—absolutely rude.”
Mabin became crimson, and the tears started to her eyes. She
had not meant to be rude, but undoubtedly her behavior had laid her
open to this accusation.
“I am stupid, clumsy; I am rude without meaning it,” she said in a
tone of such excessive humility and penitence that it was impossible
to doubt her sincerity. “I am very sorry. But you shouldn’t take any
notice of what I do or say. Nobody does at home. When I am more
awkward and tiresome than usual, they always say: ‘Oh, it’s only
Mabin!’ And then nobody minds.”
“Ah, well, I can’t quite feel like that—that it’s only Mabin. When one
likes a person, and wants to be good friends, very good friends with
that person, just as one used to be when that person and one’s self
were little things in short frocks and knickerbockers, it is very
disheartening to find that person so determined to be—er—to be—er
—so reserved that when one sits beside that person as I did last
night, you know, she will only let one see so much of her right ear as
to practically turn her back to one!”
“I didn’t!”
“You did though. And it is what you were doing again just now until
the horror of hearing the truth made you turn around to fly at me! You
did turn your back upon me last night, Miss Rose, and you hurt my
feelings.”
“Indeed, you did not seem to be hurt. You seemed to be enjoying
yourself very much!”
“Well, so I was in a way. But I should have enjoyed myself much
more if you had been as nice as you were in the garden.”
Mabin heaved a deep sigh.
“It’s no use expecting me to be nice,” she said in a voice of
despair, “I can only manage it so very seldom.”
“Well, could you hold out some signal, such as by wearing a
particular flower, or color, or some especial knot of ribbon, to let one
know when one may speak to you without being snubbed?”
“No, I couldn’t,” retorted Mabin with great fierceness, but with a
twinkle of fun in her gray eyes, which gave greater hopes than her
words did. “It is of no use for me to promise more than I can perform.
You had much better look upon me as a decidedly disagreeable
person, with rare moments of proper behavior.”
“Proper behavior, then, means niceness? I’m glad you think it
proper to be nice to me!” said Rudolph. “I perceive that I’ve lighted
upon one of the ‘rare moments,’ and I’m going to take advantage of
it,” he added, as he came a little nearer to her, and looked up in her
face with a glance of amusement and admiration which made her
blush a little. “I’m going to make you talk to me, and amuse me, as
you were told to do last night.”
“No! It was you who were told to amuse me!”
“Was it? Well, we’ll take it in turn then. Do you remember how I
taught you cricket?”
“Yes, oh yes.”
“And what a rage you used to be in when you were caught out?”
“Yes,” answered Mabin, “I remember; but I don’t want to talk about
cricket. I want to tell you something. Mrs. Dale has a fancy that ‘The
Towers’ is haunted.”
And she related the adventure of the previous night, and her
intention of changing rooms with her hostess.
Rudolph listened gravely, and there was a pause when she had
finished before he made any comment. Then he said abruptly:
“You are not nervous, are you, Mabin? I know you used to have no
end of pluck.”
“Well, I haven’t any less than I ever had.”
“Well, if you do change rooms, you have got to be prepared to see
the ghost yourself.”
“You make me feel rather—rather creepy! What do you really think
I shall see?”
“A face at the window probably. The face of the spy from your
house. What else can she have seen?”
Mabin considered a moment.
“I’ll risk it!” she cried at last. “I shan’t go to bed at all. I shall sit up
and watch.”
“I wish you would. We should find out something if you had the
strength of mind to do that.”
Not without a wild beating of the heart, Mabin undertook the task
of holding the strange night-watch, without saying a word to Mrs.
Dale of her intention.
“She thinks she only had a dreadful dream, you know,” said Mabin.
“Well,” replied Rudolph, “I want to know what sort of dream you
will have.”
He had to admire the courage she showed in undertaking a task
which was, as she expressed it, “rather shuddery,” but when he left
her at the gate of “The Towers” she was still steadfast in her
intention.
It was not until after dinner that evening that Mrs. Dale introduced
the young girl to the apartment she was to occupy that night. Mabin
was astonished at its dinginess, its gloominess, contrasting so
strongly as they did with the fresh prettiness of the room which had
been prepared for herself.
It was a large square room, with a mouldy old-fashioned wall-
paper, on which unnatural pink roses climbed up a succession of thin
hop poles. The pictures were groups of trees, done with the pencil in
the woolly early Victorian manner, and stiff bouquets, in water-color,
of conventional early Victorian flowers. The bed, which was hung
with green curtains, occupied an undue space; and Mabin felt that, in
the weird circumstances of her tenancy of the room, she would have
died rather than sleep in that funereal erection.
When Mrs. Dale had kissed her and bade her good-night, after
receiving Mabin’s assurance that she did not feel in the least
nervous, the young girl felt a strong inclination to follow her friend out
of the room, and to implore her to find her some other sleeping-
place.
By a valiant effort, however, she conquered this weakness, and
made a careful survey of her surroundings. In the first place, the
windows and their fastenings had to be examined. They were
carefully secured, and were both so high above the ground that it
would have been impossible for an intruder to reach them without a
ladder.
There were three doors; and at first Mabin was inclined to regard
this as a disquieting circumstance. But on finding that two of them
were unused, locked, and without a key, and that there was a bolt on
the door by which she had entered, she began to feel more at ease.
Exchanging her frock for a dressing-gown, and providing herself
with a book, she placed herself in an arm-chair which stood near the
fireplace, which, although shabby, was sufficiently comfortable, and,
putting her candles on a small table beside her, settled herself to
read. Her book was a novel of an excellent type, not too clever to be
charming, not so commonplace as to be dull. Much to her own
surprise, she got interested, and forgot, or almost forgot, the vague
fears which kept her in the arm-chair instead of in bed.
She was in the very heart of the book, and her candles had burnt
low in their sockets, when a sound, a very slight sound, behind her
back, caused the blood almost to freeze in her veins.
It was a soft, stealthy tread.
Looking round, half paralyzed with terror, she saw that the door
was ajar, and that creeping softly round toward the inside handle
was the long, thin hand of a man.
CHAPTER IX.
A PICTURE.
In the ordinary course of things, it would have been natural for

Mabin to conclude, on seeing a man’s hand inside her door in the
middle of the night, that the intruder was a burglar. But her mind had
been rendered more clear, her perceptions more acute, by the
stimulating mystery which she had been for the past two days trying
to solve.
Instead, therefore, of screaming, or stretching out her hand to the
old-fashioned bell-rope which hung by the fireside at a little distance
from her right hand, she waited, watched, and listened. Apparently
she had unconsciously made some slight noise as she turned in her
chair to look behind her, for the intruder, whoever he was, instead of
entering, waited and listened also.
There was a pause; and then the hand which had crept so
stealthily round the door was slowly and quietly withdrawn. Mabin,
fascinated, watched the long, bloodless fingers as they gradually
disappeared from her sight; and was sufficiently self-possessed to
observe that the hand was that of a gentleman. And upon this
discovery there sprang up in her mind a strong curiosity to see the
face of the intruder.
Even while she felt the last remains of fear give place to courage
and vivid interest, Mabin, with her wits all sharpened with
excitement, wondered at the change in herself. She sprang lightly to
her feet, and with the intention of taking him by surprise, ran lightly
round on the tips of her toes toward the door. But the candles,
flickering in the draught caused by her light hanging sleeves, caused
the shadows on the dingy rose-covered wall to dance and quiver.
The mysterious visitor, as much on the alert as the girl was, closed
the door softly between her and himself.
Mabin, however, sprang forward and seized the door-handle. She
heard the sound of rapid footsteps on the other side, and for one
moment she hesitated to go in pursuit. With the clearness of intellect

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Chemistry The Molecular Science 5th

Edition Moore Solutions Manual

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–)

D (16 e–) E (16 e–) F (26 e– and 40 e–)

G (14 e– and 28 e–) H (24 e–) I (14 e–)

82. Result: N2 has weaker IM forces.

There are other possible answers.

ICl2+ 7 + 2(7) – 1 AX2E2 tetrahe- Angular 109.5°

ICl3 7 + 3(7) AX3E2 triangular T-shaped 90°

ICl4– 7 + 4(7) + 1 AX4E2 octahedral square 90°

Molecule Number of Lewis structure Type Electron- Molecular Bond

IO4– 7 + 4(6) + 1 AX4E0 tetrahe- tetrahe- 109.5°

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

IF5 7 + 5(7) AX4E1 octahedral square 90°