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Student Study Guide
and Solutions Manual, 3e
for
Organic Chemistry, 3e
David Klein
Johns Hopkins University
www.MyEbookNiche.eCrater.com
This book is printed on acid free paper. 
Founded in 1807, John Wiley & Sons, Inc. has been a valued source of knowledge and understanding for
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Copyright  2017, 2015, 2012 John Wiley & Sons, Inc. All rights reserved. No part of this publication
may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic,
mechanical, photocopying, recording, scanning or otherwise, except as permitted under Sections 107 or
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Evaluation copies are provided to qualified academics and professionals for review purposes only, for
use in their courses during the next academic year. These copies are licensed and may not be sold or
transferred to a third party. Upon completion of the review period, please return the evaluation copy to
Wiley. Return instructions and a free of charge return shipping label are available at
www.wiley.com/go/return label. Outside of the United States, please contact your local representative.
ISBN: 978‐1‐119‐37869‐3
Printed in the United States of America
10 9 8 7 6 5 4 3 2 1
The inside back cover will contain printing identification and country of origin if omitted from this page.
In addition, if the ISBN on the back cover differs from the ISBN on this page, the one on the back cover is
correct.
CONTENTS
Chapter 1 – Electrons, Bonds, and Molecular Properties 1

Chapter 2 – Molecular Representations 28
Chapter 3 – Acids and Bases 70
Chapter 4 – Alkanes and Cycloalkanes 102
Chapter 5 – Stereoisomerism 130
Chapter 6 – Chemical Reactivity and Mechanisms 159
Chapter 7 – Alkyl Halides: Nucleophilic Substitution and Elimination Reactions 179
Chapter 8 – Addition Reactions of Alkenes 234
Chapter 9 – Alkynes 277
Chapter 10 – Radical Reactions 320
Chapter 11 – Synthesis 358
Chapter 12 – Alcohols and Phenols 392
Chapter 13 – Ethers and Epoxides; Thiols and Sulfides 441
Chapter 14 – Infrared Spectroscopy and Mass Spectrometry 489
Chapter 15 – Nuclear Magnetic Resonance Spectroscopy 518
Chapter 16 – Conjugated Pi Systems and Pericyclic Reactions 562
Chapter 17 – Aromatic Compounds 603
Chapter 18 – Aromatic Substitution Reactions 635
Chapter 19 – Aldehydes and Ketones 702
Chapter 20 – Carboxylic Acids and Their Derivatives 772
Chapter 21 – Alpha Carbon Chemistry: Enols and Enolates 830
Chapter 22 – Amines 907
Chapter 23 – Introduction to Organometallic Compounds 965
Chapter 24 – Carbohydrates 1019
Chapter 25 – Amino Acids, Peptides, and Proteins 1045
Chapter 26 – Lipids 1068
Chapter 27 – Synthetic Polymers 1083
HOW TO USE THIS BOOK
Organic chemistry is much like bicycle riding. You cannot learn how to ride a bike by watching
other people ride bikes. Some people might fool themselves into believing that it’s possible to
become an expert bike rider without ever getting on a bike. But you know that to be incorrect
(and very naïve). In order to learn how to ride a bike, you must be willing to get on the bike,
and you must be willing to fall. With time (and dedication), you can quickly train yourself to
avoid falling, and to ride the bike with ease and confidence. The same is true of organic
chemistry. In order to become proficient at solving problems, you must “ride the bike”. You
must try to solve the problems yourself (without the solutions manual open in front of you).
Once you have solved the problems, this book will allow you to check your solutions. If,
however, you don’t attempt to solve each problem on your own, and instead, you read the
problem statement and then immediately read the solution, you are only hurting yourself. You
are not learning how to avoid falling. Many students make this mistake every year. They use
the solutions manual as a crutch, and then they never really attempt to solve the problems on
their own. It really is like believing that you can become an expert bike rider by watching
hundreds of people riding bikes. The world doesn’t work that way!
The textbook has thousands of problems to solve. Each of these problems should be viewed as
an opportunity to develop your problem‐solving skills. By reading a problem statement and
then reading the solution immediately (without trying to solve the problem yourself), you are
robbing yourself of the opportunity provided by the problem. If you repeat that poor study
habit too many times, you will not learn how to solve problems on your own, and you will not
get the grade that you want.
Why do so many students adopt this bad habit (of using the solutions manual too liberally)?
The answer is simple. Students often wait until a day or two before the exam, and then they
spend all night cramming. Sound familiar? Unfortunately, organic chemistry is the type of
course where cramming is insufficient, because you need time in order to ride the bike yourself.
You need time to think about each problem until you have developed a solution on your own.
For some problems, it might take days before you think of a solution. This process is critical for
learning this subject. Make sure to allot time every day for studying organic chemistry, and use
this book to check your solutions. This book has also been designed to serve as a study guide,
as described below.
WHAT’S IN THIS BOOK
This book contains more than just solutions to all of the problems in the textbook. Each
chapter of this book also contains a series of exercises that will help you review the concepts,
skills and reactions presented in the corresponding chapter of the textbook. These exercises
are designed to serve as study tools that can help you identify your weak areas. Each chapter
of this solutions manual/study guide has the following parts:
 Review of Concepts. These exercises are designed to help you identify which concepts
are the least familiar to you. Each section contains sentences with missing words
(blanks). Your job is to fill in the blanks, demonstrating mastery of the concepts. To
verify that your answers are correct, you can open your textbook to the end of the
corresponding chapter, where you will find a section entitled Review of Concepts and
Vocabulary. In that section, you will find each of the sentences, verbatim.
 Review of Skills. These exercises are designed to help you identify which skills are the
least familiar to you. Each section contains exercises in which you must demonstrate
mastery of the skills developed in the SkillBuilders of the corresponding textbook
chapter. To verify that your answers are correct, you can open your textbook to the end
of the corresponding chapter, where you will find a section entitled SkillBuilder Review.
In that section, you will find the answers to each of these exercises.
 Review of Reactions. These exercises are designed to help you identify which reagents
are not at your fingertips. Each section contains exercises in which you must
demonstrate familiarity with the reactions covered in the textbook. Your job is to fill in
the reagents necessary to achieve each reaction. To verify that your answers are
correct, you can open your textbook to the end of the corresponding chapter, where
you will find a section entitled Review of Reactions. In that section, you will find the
answers to each of these exercises.
 Common Mistakes to Avoid. This is a new feature to this edition. The most common
student mistakes are described, so that you can avoid them when solving problems.
 A List of Useful Reagents. This is a new feature to this edition. This list provides a
review of the reagents that appear in each chapter, as well as a description of how each
reagent is used.
 Solutions. At the end of each chapter, you’ll find detailed solutions to all problems in the
textbook, including all SkillBuilders, conceptual checkpoints, additional problems,
integrated problems, and challenge problems.
The sections described above have been designed to serve as useful tools as you study and
learn organic chemistry. Good luck!
David Klein
Senior Lecturer, Department of Chemistry
Johns Hopkins University
This page intentionally left blank
Chapter 1
A Review of General Chemistry:
Electrons, Bonds and Molecular Properties
Review of Concepts
Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of
Chapter 1. Each of the sentences below appears verbatim in the section entitled Review of Concepts and
Vocabulary.
 _____________ isomers share the same molecular formula but have different connectivity of
atoms and different physical properties.
 Second-row elements generally obey the _______ rule, bonding to achieve noble gas electron
configuration.
 A pair of unshared electrons is called a ______________.
 A formal charge occurs when an atom does not exhibit the appropriate number of
___________________________.
 An atomic orbital is a region of space associated with ____________________, while a
molecular orbital is a region of space associated with _______________.
 Methane’s tetrahedral geometry can be explained using four degenerate _____-hybridized
orbitals to achieve its four single bonds.
 Ethylene’s planar geometry can be explained using three degenerate _____-hybridized orbitals.
 Acetylene’s linear geometry is achieved via _____-hybridized carbon atoms.
 The geometry of small compounds can be predicted using valence shell electron pair repulsion
(VSEPR) theory, which focuses on the number of  bonds and _______________
exhibited by each atom.
 The physical properties of compounds are determined by __________________ forces, the
attractive forces between molecules.
 London dispersion forces result from the interaction between transient __________________
and are stronger for larger alkanes due to their larger surface area and ability to accommodate
more interactions.
Review of Skills
Fill in the blanks and empty boxes below. To verify that your answers are correct, look in your textbook at
the end of Chapter 1. The answers appear in the section entitled SkillBuilder Review.
SkillBuilder 1.1 Drawing Constitutional Isomers of Small Molecules
2 CHAPTER 1
SkillBuilder 1.2 Drawing the Lewis Dot Structure of an Atom
SkillBuilder 1.3 Drawing the Lewis Structure of a Small Molecule
SkillBuilder 1.4 Calculating Formal Charge
SkillBuilder 1.5 Locating Partial Charges Resulting from Induction
SkillBuilder 1.6 Identifying Electron Configurations
SkillBuilder 1.7 Identifying Hybridization States
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CHAPTER 1 3
SkillBuilder 1.8 Predicting Geometry
SkillBuilder 1.9 Identifying the Presence of Molecular Dipole Moments
SkillBuilder 1.10 Predicting Physical Properties
A Common Mistake to Avoid

When drawing a structure, don’t forget to draw formal charges, as forgetting to do so is a common error. If
a formal charge is present, it MUST be drawn. For example, in the following case, the nitrogen atom bears
a positive charge, so the charge must be drawn:
As we progress though the course, we will see structures of increasing complexity. If formal charges are
present, failure to draw them constitutes an error, and must be scrupulously avoided. If you have trouble
drawing formal charges, go back and master that skill. You can’t go on without it. Don’t make the mistake
of underestimating the importance of being able to draw formal charges with confidence.
4 CHAPTER 1
Solutions
1.1. Finally, we can draw three carbon atoms in a linear
(a) Begin by determining the valency of each atom that fashion, and then draw the remaining two carbon atoms
appears in the molecular formula. The carbon atoms are on separate branches.
tetravalent, while the chlorine atom and hydrogen atoms
are all monovalent. The atoms with more than one bond
(in this case, the three carbon atoms) should be drawn in
the center of the compound. Then, the chlorine atom can
be placed in either of two locations: i) connected to the
central carbon atom, or ii) connected to one of the other Note that we cannot place the last two carbon atoms
two (equivalent) carbon atoms. The hydrogen atoms are together as one branch, because that possibility has
then placed at the periphery. already been drawn earlier (a linear chain of four carbon
atoms with a single branch):
(b) Begin by determining the valency of each atom that

appears in the molecular formula. The carbon atoms are
tetravalent, while the hydrogen atoms are all In summary, there are three different ways to connect
monovalent. The atoms with more than one bond (in this five carbon atoms:
case, the four carbon atoms) should be drawn in the
center of the compound. There are two different ways to
connect four carbon atoms. They can either be arranged
in a linear fashion or in a branched fashion:
We then place the hydrogen atoms at the periphery,
giving the following three constitutional isomers:
H H H H H
H C C C C C H
H
We then place the hydrogen atoms at the periphery, H H H H H
H C H
giving the following two constitutional isomers: H H H
H C H H C C C H
H H H
H H
H C C C C H H C H
H H H H H
(d) Begin by determining the valency of each atom that

(c) Begin by determining the valency of each atom that
tetravalent, the oxygen atom is divalent, and the
hydrogen atoms are all monovalent. Any atoms with
tetravalent, while the hydrogen atoms are all
more than one bond (in this case, the four carbon atoms
monovalent. The atoms with more than one bond (in this
and the one oxygen atom) should be drawn in the center
case, the five carbon atoms) should be drawn in the
of the compound, with the hydrogen atoms at the
center of the compound. So we must explore all of the
periphery. There are several different ways to connect
different ways to connect five carbon atoms. First, we
four carbon atoms and one oxygen atom. Let’s begin
can connect all five carbon atoms in a linear fashion:
with the four carbon atoms. There are two different
ways to connect four carbon atoms. They can either be
arranged in a linear fashion or in a branched fashion.
Alternatively, we can draw four carbon atoms in a linear

fashion, and then draw the fifth carbon atom on a branch.
There are many ways to draw this possibility:
Next, the oxygen atom must be inserted. For each of the

two skeletons above (linear or branched), there are
CHAPTER 1 5
several different locations to insert the oxygen atom. Furthermore, we can place both chlorine atoms at C2,
The linear skeleton has four possibilities, shown here: giving a new possibility not shown above:
There are no other possibilities. For example, placing

the two chlorine atoms at C2 and C3 is equivalent to
and the branched skeleton has three possibilities shown
placing them at C1 and C2:
here:
Finally, we complete all of the structures by drawing the Finally, the hydrogen atoms are placed at the periphery,
bonds to hydrogen atoms. giving the following four constitutional isomers:
1.2. The carbon atoms are tetravalent, while the chlorine

atoms and fluorine atoms are all monovalent. The atoms
with more than one bond (in this case, the two carbon
atoms) should be drawn in the center of the compound.
The chlorine atoms and fluorine atoms are then placed at
the periphery, as shown. There are only two possible
constitutional isomers: one with the three chlorine atoms
all connected to the same carbon, and one in which they
are distributed over both carbon atoms. Any other
representations that one may draw must be one of these
structures drawn in a different orientation.
(e) Begin by determining the valency of each atom that

tetravalent, while the chlorine atom and hydrogen atoms
are all monovalent. The atoms with more than one bond
(in this case, the three carbon atoms) should be drawn in 1.3.
the center of the compound. There is only way to (a) Carbon belongs to group 4A of the periodic table,
connect three carbon atoms: and it therefore has four valence electrons. The periodic
symbol for carbon (C) is drawn, and each valence
electron is placed by itself (unpaired), around the C, like
this:
Next, we must determine all of the different possible
ways of connecting two chlorine atoms to the chain of
three carbon atoms. If we place one chlorine atom at C1,
then the second chlorine atom can be placed at C1, at C2 (b) Oxygen belongs to group 6A of the periodic table,
or at C3: and it therefore has six valence electrons. The periodic
symbol for oxygen (O) is drawn, and each valence
electron is placed by itself (unpaired) on a side of the O,
until all four sides are occupied. That takes care of four
of the six electrons, leaving just two more electrons to
6 CHAPTER 1
draw. Each of the two remaining electrons is then paired (h) Iodine belongs to group 7A of the periodic table, and
up with an electron already drawn, like this: it therefore has seven valence electrons. The periodic
symbol for iodine (I) is drawn, and each valence electron
is placed by itself (unpaired) on a side of the I, until all
four sides are occupied. That takes care of four of the
seven electrons, leaving three more electrons to draw.
(c) Fluorine belongs to group 7A of the periodic table, Each of the three remaining electrons is then paired up
and it therefore has seven valence electrons. The with an electron already drawn, like this:
periodic symbol for fluorine (F) is drawn, and each
valence electron is placed by itself (unpaired) on a side
of the F, until all four sides are occupied. That takes care
of four of the seven electrons, leaving three more
electrons to draw. Each of the three remaining electrons 1.4. Both nitrogen and phosphorus belong to group 5A
is then paired up with an electron already drawn, like of the periodic table, and therefore, each of these atoms
this: has five valence electrons. In order to achieve an octet,
we expect each of these elements to form three bonds.
1.5. Aluminum is directly beneath boron on the periodic

(d) Hydrogen belongs to group 1A of the periodic table, table (group 3A), and each of these elements has three
and it therefore has one valence electron. The periodic valence electrons. Therefore, we expect the bonding
symbol for hydrogen (H) is drawn, and the one and only properties to be similar.
valence electron is placed on a side of the H, like this:
1.6. The Lewis dot structure for a carbon atom is shown
in the solution to Problem 1.3a. That drawing must be
modified by removing one electron, resulting in a formal
(e) Bromine belongs to group 7A of the periodic table, positive charge, as shown below. This resembles boron
and it therefore has seven valence electrons. The because it exhibits three valence electrons.
periodic symbol for bromine (Br) is drawn, and each
valence electron is placed by itself (unpaired) on a side
of the Br, until all four sides are occupied. That takes
care of four of the seven electrons, leaving three more
electrons to draw. Each of the three remaining electrons 1.7.
is then paired up with an electron already drawn, like (a) Lithium is in Group 1A of the periodic table, and
this: therefore, it has just one valence electron.
Li
(f) Sulfur belongs to group 6A of the periodic table, and (b) If an electron is removed from a lithium atom, the
it therefore has six valence electrons. The periodic resulting cation has zero valence electrons.
symbol for sulfur (S) is drawn, and each valence electron
is placed by itself (unpaired) on a side of the S, until all
four sides are occupied. That takes care of four of the 1.8.
six electrons, leaving just two more electrons to draw. (a) Each carbon atom has four valence electrons, and
Each of the two remaining electrons is then paired up each hydrogen atom has one valence electron. Only the
with an electron already drawn, like this: carbon atoms can form more than one bond, so we begin
by connecting the carbon atoms to each other. Then, we
connect all of the hydrogen atoms, as shown.
(g) Chlorine belongs to group 7A of the periodic table,

and it therefore has seven valence electrons. The
periodic symbol for chlorine (Cl) is drawn, and each
valence electron is placed by itself (unpaired) on a side (b) Each carbon atom has four valence electrons, and
of the Cl, until all four sides are occupied. That takes each hydrogen atom has one valence electron. Only the
care of four of the seven electrons, leaving three more carbon atoms can form more than one bond, so we begin
electrons to draw. Each of the three remaining electrons by connecting the carbon atoms to each other. Then, we
is then paired up with an electron already drawn, like connect all of the hydrogen atoms, and the unpaired
this: electrons are shared to give a double bond. In this way,
each of the carbon atoms achieves an octet.
CHAPTER 1 7
(c) Each carbon atom has four valence electrons, and

each hydrogen atom has one valence electron. Only the
carbon atoms can form more than one bond, so we begin
connect all of the hydrogen atoms, and the unpaired
electrons are shared to give a triple bond. In this way,
(d) Each carbon atom has four valence electrons, and For each of these possible arrangements, we connect the
each hydrogen atom has one valence electron. Only the hydrogen atoms, giving the following four constitutional
carbon atoms can form more than one bond, so we begin isomers.
connect all of the hydrogen atoms, as shown.
(e) Each carbon atom has four valence electrons, and

connect all of the hydrogen atoms, and the unpaired In each of these four structures, the nitrogen atom has
electrons are shared to give a double bond. In this way, one lone pair.
1.11.
(a) The carbon atom has four valence electrons, the
nitrogen atom has five valence electrons and the
hydrogen atom has one valence electron. Only the
(f) The carbon atom has four valence electrons, the carbon atom and the nitrogen atom can form more than
oxygen atom has six valence electrons, and each one bond, so we begin by connecting them to each other.
hydrogen atom has one valence electron. Only the Then, we connect the hydrogen atom to the carbon, as
carbon atom and the oxygen atom can form more than shown. The unpaired electrons are shared to give a triple
one bond, so we begin by connecting them to each other. bond. In this way, both the carbon atom and the nitrogen
Then, we connect all of the hydrogen atoms, as shown. atom achieve an octet.
(b) Each carbon atom has four valence electrons, and

1.9. Boron has three valence electrons, each of which is by connecting the carbon atoms to each other. Then, we
shared with a hydrogen atom, shown below. The central connect all of the hydrogen atoms as indicated in the
boron atom lacks an octet of electrons, and it is therefore given condensed formula (CH2CHCHCH2), and the
very unstable and reactive. unpaired electrons are shared to give two double bonds
on the outermost carbons. In this way, each of the carbon
atoms achieves an octet.
1.10. Each of the carbon atoms has four valence

electrons; the nitrogen atom has five valence electrons;
and each of the hydrogen atoms has one valence 1.12.
electron. We begin by connecting the atoms that have (a) Aluminum is in group 3A of the periodic table, and
more than one bond (in this case, the three carbon atoms it should therefore have three valence electrons. In this
and the nitrogen atom). There are four different ways case, the aluminum atom exhibits four valence electrons
that these four atoms can be connected to each other, (one for each bond). With one extra electron, this
shown here. aluminum atom will bear a negative charge.
8 CHAPTER 1
the oxygen atom exhibits only five valence electrons

(one for each bond, and two for the lone pair). This
oxygen atom is missing an electron, and it therefore
bears a positive charge.
(b) Oxygen is in group 6A of the periodic table, and it
should therefore have six valence electrons. In this case,
the oxygen atom exhibits only five valence electrons
(one for each bond, and two for the lone pair). This
oxygen atom is missing an electron, and it therefore
bears a positive charge. (h) Two of the atoms in this structure exhibit a formal
charge because each of these atoms does not exhibit the
appropriate number of valence electrons. The aluminum
atom (group 3A) should have three valence electrons, but
it exhibits four (one for each bond). With one extra
electron, this aluminum atom will bear a negative charge.
(c) Nitrogen is in group 5A of the periodic table, and it The neighboring chlorine atom (to the right) should have
should therefore have five valence electrons. In this seven valence electrons, but it exhibits only six (one for
case, the nitrogen atom exhibits six valence electrons each bond and two for each lone pair). It is missing one
(one for each bond and two for each lone pair). With electron, so this chlorine atom will bear a positive
one extra electron, this nitrogen atom will bear a charge.
negative charge.
(i) Two of the atoms in this structure exhibit a formal

(d) Oxygen is in group 6A of the periodic table, and it charge because each of these atoms does not exhibit the
should therefore have six valence electrons. In this case, appropriate number of valence electrons. The nitrogen
the oxygen atom exhibits only five valence electrons atom (group 5A) should have five valence electrons, but
(one for each bond, and two for the lone pair). This it exhibits four (one for each bond). It is missing one
oxygen atom is missing an electron, and it therefore electron, so this nitrogen atom will bear a positive
bears a positive charge. charge. One of the two oxygen atoms (the one on the
right) exhibits seven valence electrons (one for the bond,
and two for each lone pair), although it should have only
six. With one extra electron, this oxygen atom will bear
a negative charge.
(e) Carbon is in group 4A of the periodic table, and it

should therefore have four valence electrons. In this
case, the carbon atom exhibits five valence electrons
(one for each bond and two for the lone pair). With one 1.13.
extra electron, this carbon atom will bear a negative (a) The boron atom in this case exhibits four valence
charge. electrons (one for each bond), although boron (group
3A) should only have three valence electrons. With one
extra electron, this boron atom bears a negative charge.
H
(f) Carbon is in group 4A of the periodic table, and it H B H
should therefore have four valence electrons. In this
H
case, the carbon atom exhibits only three valence
electrons (one for each bond). This carbon atom is (b) Nitrogen is in group 5A of the periodic table, so a
missing an electron, and it therefore bears a positive nitrogen atom should have five valence electrons. A
charge. negative charge indicates one extra electron, so this
nitrogen atom must exhibit six valence electrons (one for
each bond and two for each lone pair).
(g) Oxygen is in group 6A of the periodic table, and it

should therefore have six valence electrons. In this case,
CHAPTER 1 9
(c) One of the carbon atoms (below right) exhibits three (b) Fluorine is more electronegative than carbon, and a
valence electrons (one for each bond), but carbon (group C–F bond is polar covalent. For a C–F bond, the F will
4A) is supposed to have four valence electrons. It is be electron-rich (‒), and the C will be electron-poor
missing one electron, so this carbon atom therefore bears (+). Chlorine is also more electronegative than carbon,
a positive charge. so a C–Cl bond is also polar covalent. For a C–Cl bond,
H H the Cl will be electron-rich (‒), and the C will be
H C C electron-poor (+), as shown below.
H H
1.14. Carbon is in group 4A of the periodic table, and it

should therefore have four valence electrons. Every
carbon atom in acetylcholine has four bonds, thus
exhibiting the correct number of valence electrons (four)
and having no formal charge. (c) Carbon is more electronegative than magnesium, so
the C will be electron-rich (‒) in a C–Mg bond, and the
Mg will be electron-poor (+). Also, bromine is more
electronegative than magnesium. So in a Mg–Br bond,
the Br will be electron-rich (‒), and the Mg will be
electron-poor (+), as shown below.
Oxygen is in group 6A of the periodic table, and it

should therefore have six valence electrons. Each oxygen
atom in acetylcholine has two bonds and two lone pairs
of electrons, so each oxygen atom exhibits six valence (d) Oxygen is more electronegative than carbon or
electrons (one for each bond, and two for each lone pair). hydrogen, so all C–O bonds and all O–H bond are polar
With the correct number of valence electrons, each covalent. For each C–O bond and each O–H bond, the O
oxygen atom will lack a formal charge.
will be electron-rich (‒), and the C or H will be
electron-poor (+), as shown below.
The nitrogen atom (group 5A) should have five valence

electrons, but it exhibits four (one for each bond). It is (e) Oxygen is more electronegative than carbon. As
missing one electron, so this nitrogen atom will bear a such, the O will be electron-rich (‒) and the C will be
positive charge. electron-poor (+) in a C=O bond, as shown below.
(f) Chlorine is more electronegative than carbon. As

such, for each C–Cl bond, the Cl will be electron-rich
1.15. (‒) and the C will be electron-poor (+), as shown
(a) Oxygen is more electronegative than carbon, and a below.
C–O bond is polar covalent. For each C–O bond, the O
will be electron rich (‒), and the C will be electron-poor
(+), as shown below.
1.16. Oxygen is more electronegative than carbon. As

such, the O will be electron-rich (‒) and the C will be
electron-poor (+) in a C=O bond. In addition, chlorine
is more electronegative than carbon. So for a C–Cl
10 CHAPTER 1
bond, the Cl will be electron-rich (‒) and the C will be missing an electron, so the electron configuration should
electron-poor (+), as shown below. be as follows: 1s22s22p1
(c) As seen in Skillbuilder 1.6, the electron configuration
of a nitrogen atom is 1s22s22p3. However, if a nitrogen
atom bears a positive charge, then it must be missing an
electron, so the electron configuration should be as
follows: 1s22s22p2
(d) The electron configuration of an oxygen atom is
1s22s22p4 (see the solution to Problem 1.18b). However,
Notice that two carbon atoms are electron-poor (+). if an oxygen atom bears a negative charge, then it must
These are the positions that are most likely to be attacked have one extra electron, so the electron configuration
by an anion, such as hydroxide. should be as follows: 1s22s22p5
1.17. Oxygen is more electronegative than carbon. As 1.20. Silicon is in the third row, or period, of the periodic
such, the O will be electron-rich (δ−) and the C will be table. Therefore, it has a filled second shell, like neon,
electron-poor (δ+) in a C─O bond. In addition, chlorine and then the additional electrons are added to the third
is more electronegative than carbon. So for a C─Cl shell. As indicated in Figure 1.10, neon has two 1s
bond, the Cl will be electron-rich (δ−) and the C will be electrons, two 2s electrons, and six 2p electrons. Silicon
electron-poor (δ+), as shown below. As you might has an additional two 3s electrons and two 3p electrons
imagine, epichlorohydrin is a very reactive molecule! to give a total of 14 electrons and an electron
configuration of 1s22s22p63s23p2.
1.21. The bond angles of an equilateral triangle are 60º,

but each bond angle of cyclopropane is supposed to be
109.5º. Therefore, each bond angle is severely strained,
causing an increase in energy. This form of strain, called
1.18. ring strain, will be discussed in Chapter 4. The ring
(a) As indicated in Figure 1.10, carbon has two 1s strain associated with a three-membered ring is greater
electrons, two 2s electrons, and two 2p electrons. This than the ring strain of larger rings, because larger rings
information is represented by the following electron do not require bond angles of 60º.
configuration: 1s22s22p2
(b) As indicated in Figure 1.10, oxygen has two 1s 1.22.
electrons, two 2s electrons, and four 2p electrons. This (a) The C=O bond of formaldehyde is comprised of one
information is represented by the following electron  bond and one  bond.
configuration: 1s22s22p4 (b) Each C‒H bond is formed from the interaction
(c) As indicated in Figure 1.10, boron has two 1s between an sp2 hybridized orbital from carbon and an s
electrons, two 2s electrons, and one 2p electron. This orbital from hydrogen.
information is represented by the following electron (c) The oxygen atom is sp2 hybridized, so the lone pairs
configuration: 1s22s22p1 occupy sp2 hybridized orbitals.
(d) As indicated in Figure 1.10, fluorine has two 1s
electrons, two 2s electrons, and five 2p electrons. This 1.23. Rotation of a single bond does not cause a
information is represented by the following electron reduction in the extent of orbital overlap, because the
configuration: 1s22s22p5 orbital overlap occurs on the bond axis. In contrast,
(e) Sodium has two 1s electrons, two 2s electrons, six 2p rotation of a  bond results in a reduction in the extent of
electrons, and one 3s electron. This information is orbital overlap, because the orbital overlap is NOT on
represented by the following electron configuration: the bond axis.
1s22s22p63s1
(f) Aluminum has two 1s electrons, two 2s electrons, six 1.24.
2p electrons, two 3s electrons, and one 3p electron. This (a) The highlighted carbon atom (below) has four
information is represented by the following electron bonds, and is therefore sp3 hybridized. The other
configuration: 1s22s22p63s23p1 carbon atoms in this structure are all sp2 hybridized,
because each of them has three bonds and one  bond.
1.19.
(a) The electron configuration of a carbon atom is H O H
1s22s22p2 (see the solution to Problem 1.18a). However,
if a carbon atom bears a negative charge, then it must H C C C
have one extra electron, so the electron configuration C H
H
should be as follows: 1s22s22p3
3 H
(b) The electron configuration of a carbon atom is sp
1s22s22p2 (see the solution to Problem 1.18a). However,
if a carbon atom bears a positive charge, then it must be (b) Each of the highlighted carbon atoms has four
bonds, and is therefore sp3 hybridized. Each of the
CHAPTER 1 11
other two carbon atoms in this structure is sp hybridized, And each of the following three highlighted carbon
because each has two bonds and two  bonds. atoms has three  bonds and one  bond, and is therefore
sp2 hybridized:
(b) Each of the highlighted carbon atoms (below) has

four bonds, and is therefore sp3 hybridized. Each of
the other two carbon atoms in this structure is sp2
hybridized, because each has three bonds and one 
bond. Finally, each of the following five highlighted carbon
atoms has two  bonds and two  bonds, and is therefore
sp hybridized.
(d) Each of the two central carbon atoms has two

bonds and two  bonds, and as such, each of these
carbon atoms is sp hybridized. The other two carbon
atoms (the outer ones) are sp2 hybridized because each 1.26. Carbon-carbon triple bonds generally have a
has three bonds and one  bond. shorter bond length than carbon-carbon double bonds,
which are generally shorter than carbon-carbon single
bonds (see Table 1.2).
(e) One of the carbon atoms (the one connected to

oxygen) has two bonds and two  bonds, and as such,
it is sp hybridized. The other carbon atom is sp2
hybridized because it has three bonds and one  bond.
1.27
(a) In this structure, the boron atom has four  bonds
and no lone pairs, giving a total of four electron pairs
(steric number = 4). VSEPR theory therefore predicts a
tetrahedral arrangement of electron pairs. Since all of
the electron pairs are bonds, the structure is expected to
have tetrahedral geometry.
1.25. Each of the following three highlighted three
(b) In this structure, the boron atom has three  bonds
carbon atoms has four  bonds, and is therefore sp3 and no lone pairs, giving a total of three electron pairs
hybridized: (steric number = 3). VSEPR theory therefore predicts a
trigonal planar geometry.
(c) In this structure, the nitrogen atom has four  sigma
bonds and no lone pairs, giving a total of four electron
pairs (steric number = 4). VSEPR theory therefore
predicts a tetrahedral arrangement of electron pairs.
Since all of the electron pairs are bonds, the structure is
expected to have tetrahedral geometry.
(d) The carbon atom has four  bonds and no lone pairs,
giving a total of four electron pairs (steric number = 4).
VSEPR theory therefore predicts a tetrahedral
12 CHAPTER 1
arrangement of electron pairs. Since all of the electron (c) The nitrogen atom has three bonds and one lone
pairs are bonds, the structure is expected to have pair (steric number = 4), and VSEPR theory predicts
tetrahedral geometry. trigonal pyramidal geometry (because one corner of the
tetrahedron is occupied by a lone pair). As such, the
1.28. In the carbocation, the carbon atom has three dipole moments associated with the N–H bonds do not
bonds and no lone pairs. Since there are a total of three fully cancel each other. There is a net molecular dipole
electron pairs (steric number = 3), VSEPR theory moment, as shown:
predicts trigonal planar geometry, with bond angles of
120⁰. In contrast, the carbon atom of the carbanion has
three bonds and one lone pair, giving a total of four
electron pairs (steric number = 4). For this ion, VSEPR
theory predicts a tetrahedral arrangement of electron
pairs, with a lone pair positioned at one corner of the (d) The central carbon atom has four bonds (steric
tetrahedron, giving rise to trigonal pyramidal geometry. number = 4), and VSEPR theory predicts tetrahedral
geometry. There are individual dipole moments
1.29. In ammonia, the nitrogen atom has three bonds associated with each of the C–Cl bonds and each of the
and one lone pair. Therefore, VSEPR theory predicts C–Br bonds. If all four dipole moments had the same
trigonal pyramidal geometry, with bond angles of magnitude, then we would expect them to completely
approximately 107⁰. In the ammonium ion, the nitrogen cancel each other to give no molecular dipole moment
atom has four bonds and no lone pairs, so VSEPR theory (as in the case of CCl4). However, the dipole moments
predicts tetrahedral geometry, with bond angles of for the C–Cl bonds are larger than the dipole moments of
109.5⁰. Therefore, we predict that the bond angles will the C–Br bonds, and as such, there is a net molecular
increase (by approximately 2.5⁰) as a result of the dipole moment, shown here:
reaction.
1.30. The silicon atom has four  bonds and no lone

pairs, so the steric number is 4 (sp3 hybridization), which
means that the arrangement of electron pairs will be
tetrahedral. With no lone pairs, the arrangement of the
atoms (geometry) is the same as the electronic (e) The oxygen atom has two bonds and two lone
arrangement. It is tetrahedral. pairs (steric number = 4), and VSEPR theory predicts
bent geometry. As such, the dipole moments associated
with the C–O bonds do not fully cancel each other.
There is a net molecular dipole moment, as shown:
1.31.
(a) This compound has three C–Cl bonds, each of which
exhibits a dipole moment. To determine if these dipole
moments cancel each other, we must identify the
molecular geometry. The central carbon atom has four (f) There are individual dipole moments associated with
bonds so we expect tetrahedral geometry. As such, the each C–O bond (just as we saw in the solution to 1.31e),
three C–Cl bonds do not lie in the same plane, and they but in this case, they fully cancel each other to give no
do not completely cancel each other out. There is a net net molecular dipole moment.
molecular dipole moment, as shown:
(g) Each C=O bond has a strong dipole moment, and
they do not fully cancel each other because they are not
pointing in opposite directions. As such, there will be a
net molecular dipole moment, as shown here:
(b) The oxygen atom has two bonds and two lone pairs
(steric number = 4), and VSEPR theory predicts bent
geometry. As such, the dipole moments associated with
the C–O bonds do not fully cancel each other. There is a
net molecular dipole moment, as shown:
(h) Each C=O bond has a strong dipole moment, and in

this case, they are pointing in opposite directions. As
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CHAPTER 1 13
such, they fully cancel each other, giving no net Therefore, there is a net molecular dipole moment, as
molecular dipole moment. shown:
(i) Each C–Cl bond has a dipole moment, and they do

not fully cancel each other because they are not pointing
in opposite directions. As such, there will be a net
molecular dipole moment, as shown here:
1.33.
(a) The latter compound is expected to have a higher
boiling point, because it is less branched.
(b) The latter compound is expected to have a higher
boiling point, because it has more carbon atoms.
(c) The latter compound is expected to have a higher
(j) Each C–Cl bond has a dipole moment, and in this boiling point, because it has an OH bond, which will lead
case, they are pointing in opposite directions. As such, to hydrogen bonding interactions.
they fully cancel each other, giving no net molecular (d) The first compound is expected to have a higher
dipole moment. boiling point, because it is less branched.
(k) Each C–Cl bond has a dipole moment, and they do 1.34. Compound 3 is expected to have a higher boiling
not fully cancel each other because they are not pointing point than compound 4, because the former has an O-H
in opposite directions. As such, there will be a net group and the latter does not. Compound 4 does not
molecular dipole moment, as shown here: have the ability to form hydrogen-bonding interactions
with itself, so it will have a lower boiling point. When
this mixture is heated, the compound that boils first (4)
can be collected, leaving behind compound 3.
(l) Each C–Cl bond has a dipole moment, but in this

case, they fully cancel each other to give no net
molecular dipole moment.
1.32. Each of the C–O bonds has an individual dipole 1.35.

moment, shown here. (a) The carbon atoms are tetravalent, and the hydrogen
atoms are all monovalent. Any atoms with more than
one bond (in this case, the six carbon atoms) should be
drawn in the center of the compound, with the hydrogen
atoms at the periphery. There are five different ways to
connect six carbon atoms, which we will organize based
on the length of the longest chain.
To determine if these individual dipole moments fully

cancel each other, we must determine the geometry
around the oxygen atom. The oxygen atom has two 
bonds and two lone pairs, giving rise to a bent geometry.
As such, the dipole moments associated with the C–O
bonds do NOT fully cancel each other.
14 CHAPTER 1
Finally, we complete all of the structures by drawing the connected to the same carbon atom or to different carbon
bonds to hydrogen atoms. atoms, as shown.
(d) The carbon atoms are tetravalent, while the chlorine

atoms and hydrogen atoms are all monovalent. The
atoms with more than one bond (in this case, the two
carbon atoms) should be drawn in the center of the
compound. The chlorine atoms and hydrogen atoms are
then placed at the periphery, and there are two different
ways to do this. One way is to connect all three chlorine
atoms to the same carbon atom. Alternatively, we can
connect two chlorine atoms to one carbon atom, and then
connect the third chlorine atom to the other carbon atom,
as shown here:
1.36.
(a) The molecular formula (C4H8) indicates that we must
draw structures with four carbon atoms and eight
(b) The carbon atoms are tetravalent, while the hydrogen atoms. The carbon atoms are tetravalent, while
chlorine atom and hydrogen atoms are all monovalent. the hydrogen atoms are all monovalent. The atoms with
The atoms with more than one bond (in this case, the two more than one bond (in this case, the four carbon atoms)
carbon atoms) should be drawn in the center of the should be drawn in the center of the compound, with the
compound. The chlorine atom and hydrogen atoms are hydrogen atoms at the periphery. When we connect four
then placed at the periphery, as shown. carbon atoms, either in a linear fashion or in a branched
fashion (see solution to 1.1b), we find that ten hydrogen
atoms are required in order for all four carbons atom to
achieve an octet (to have four bonds).
The chlorine atom can be placed in any one of the six

available positions. The following six drawings all
represent the same compound, in which the two carbon
atoms are connected to each other, and the chlorine atom
is connected to one of the carbon atoms.
But the molecular formula (C4H8) indicates only eight

hydrogen atoms, so we must remove two hydrogen
atoms. This gives two carbon atoms that lack an octet,
because each of them has an unpaired electron.
(c) The carbon atoms are tetravalent, while the chlorine

atoms and hydrogen atoms are all monovalent. The
atoms with more than one bond (in this case, the two
carbon atoms) should be drawn in the center of the
compound. The chlorine atoms and hydrogen atoms are
then placed at the periphery, and there are two different
ways to do this. The two chlorine atoms can either be
CHAPTER 1 15
These electrons can be paired as a double bond: we can imagine arranging the carbon atoms either in a
linear fashion or in a branched fashion:
In the linear skeleton, there are two locations where we

but the problem statement directs us to draw only those can place the double bond:
constitutional isomers in which all of the bonds are
single bonds. So we must think of another way to pair
up the unpaired electrons. It is difficult to see how this
can be accomplished if the unpaired electrons are on
adjacent carbon atoms. But suppose the unpaired
electrons are on distant carbon atoms:
Notice that the double bond can be placed at C1-C2 or at
C2-C3 (placing the double bond at C3-C4 is the same as
placing it at C1-C2, because we can just assign numbers
in the opposite direction).
Now let’s explore the branched skeleton. There is only
one location to place the double bond in a branched
skeleton, because the following three drawings represent
the same compound:
When drawn like this, it becomes apparent that we can

pair the unpaired electrons by forming a C–C bond,
giving a ring:
In summary, there are three constitutional isomers of

C4H8 that contain a double bond:
When the structure contains a ring, then eight hydrogen

atoms are sufficient to provide all four carbon atoms
with an octet of electrons. The ring can either be a 3-
membered ring or a 4-membered ring, giving the
following two constitutional isomers:
1.37.
(a) According to Table 1.1, the difference in
electronegativity between Br and H is 2.8 – 2.1 = 0.7, so
an H–Br bond is expected to be polar covalent. Since
bromine is more electronegative than hydrogen, the Br
will be electron rich (‒), and the H will be electron-poor
(+), as shown below:
(b) See the solution to part (a) as an introduction to the

following solution.
Since the unpaired electrons were paired as a double (b) According to Table 1.1, the difference in
bond (rather than as a ring), we are looking for electronegativity between Cl and H is 3.0 – 2.1 = 0.9, so
compounds that contain one double bond and do NOT an H–Cl bond is expected to be polar covalent. Since
have a ring. Since the structure does not contain a ring, chlorine is more electronegative than hydrogen, the Cl
16 CHAPTER 1
will be electron rich (‒), and the H will be electron-poor The unpaired electrons are then paired up to give a triple
(+), as shown below: bond. In this way, each of the atoms achieves an octet.
(c) According to Table 1.1, the difference in

electronegativity between O and H is 3.5 – 2.1 = 1.4, so
an O–H bond is expected to be polar covalent. Oxygen
is more electronegative than hydrogen, so for each O–H 1.40. Each of the carbon atoms has four valence
bond, the O will be electron rich (‒) and the H will be electrons; the nitrogen atom has five valence electrons;
electron-poor (+), as shown below: and each of the hydrogen atoms has one valence
electron. We begin by connecting the atoms that have
more than one bond (in this case, the four carbon atoms
and the nitrogen atom). The problem statement indicates
how we should connect them:
(d) Oxygen (3.5) is more electronegative than carbon

(2.5) or hydrogen (2.1), and a C–O or H–O bond is polar
covalent. For each C–O or H–O bond, the O will be
electron rich (‒), and the C or H will be electron-poor
(+), as shown below:
Then, we connect all of the hydrogen atoms, as shown.
1.38.
(a) The difference in electronegativity between Na (0.9)
and Br (2.8) is greater than the difference in
electronegativity between H (2.1) and Br (2.8). The nitrogen atom has three bonds and one lone pair,
Therefore, NaBr is expected to have more ionic character so the steric number is 4, which means that the
than HBr. arrangement of electron pairs is expected to be
(b) The difference in electronegativity between F (4.0) tetrahedral. One corner of the tetrahedron is occupied by
and Cl (3.0) is greater than the difference in a lone pair, so the geometry of the nitrogen atom (the
electronegativity between Br (2.8) and Cl (3.0). arrangement of atoms around that nitrogen atom) is
Therefore, FCl is expected to have more ionic character trigonal pyramidal. As such, the individual dipole
than BrCl. moments associated with the C–N bonds do not fully
cancel each other. There is a net molecular dipole
moment, as shown:
1.39.
(a) Each carbon atom has four valence electrons, the
oxygen atom has six valence electrons, and each
hydrogen atom has one valence electron. In this case,
the information provided in the problem statement
(CH3CH2OH) indicates how the atoms are connected to
each other:
1.41. Bromine is in group 7A of the periodic table, so
each bromine atom has seven valence electrons.
Aluminum is in group 3A of the periodic table, so
aluminum is supposed to have three valence electrons,
but the structure bears a negative charge, which means
that there is one extra electron. That is, the aluminum
atom has four valence electrons, rather than three, which
(b) Each carbon atom has four valence electrons, the
is why it has a formal negative charge. This gives the
nitrogen atom has five valence electrons, and each
following Lewis structure:
hydrogen atom has one valence electron. In this case,
the information provided in the problem statement
(CH3CN) indicates how the atoms are connected to each
other:
CHAPTER 1 17
The aluminum atom has four bonds and no lone pairs, so (c) The oxygen atom has two bonds and two lone pairs
the steric number is 4, which means that this aluminum (steric number = 4), and VSEPR predicts bent geometry.
atom will have tetrahedral geometry. As such, the dipole moments associated with the O–H
bonds do not cancel each other. There is a net molecular
1.42. The molecular formula of cyclopropane is C3H6, so dipole moment, as shown:
we are looking for a different compound that has the
same molecular formula, C3H6. That is, we need to find
another way to connect the carbon atoms, other than in a
ring (there is only one way to connect three carbon atoms
in a ring, so we must be looking for something other than
a ring). If we connect the three carbon atoms in a linear (d) The central carbon atom of carbon dioxide (CO2) has
fashion and then complete the drawing by placing two bonds and no lone pairs, so it is sp hybridized and
hydrogen atoms at the periphery, we notice that the is expected to have linear geometry. Each C=O bond has
molecular formula (C3H8) is not correct: a strong dipole moment, but in this case, they are
pointing in opposite directions. As such, they fully
cancel each other, giving no net molecular dipole
moment.
(e) Carbon tetrachloride (CCl4) has four C–Cl bonds,

each of which exhibits a dipole moment. However, the
We are looking for a structure with the molecular central carbon atom has four bonds so it is expected to
formula C3H6. If we remove two hydrogen atoms from have tetrahedral geometry. As such, the four dipole
our drawing, we are left with two unpaired electrons, moments completely cancel each other out, and there is
indicating that we should consider drawing a double no net molecular dipole moment.
bond:
(f) This compound has two C–Br bonds, each of which
exhibits a dipole moment. To determine if these dipole
moments cancel each other, we must identify the
molecular geometry. The central carbon atom has four
bonds so it is expected to have tetrahedral geometry.
As such, the C–Br bonds do not completely cancel each
other out. There is a net molecular dipole moment, as
shown:
The structure of this compound (called propylene) is

different from the structure of cyclopropane, but both 1.44.
compounds share the same molecular formula, so they (a) As indicated in Figure 1.10, oxygen has two 1s
are constitutional isomers. electrons, two 2s electrons, and four 2p electrons.
(b) As indicated in Figure 1.10, fluorine has two 1s
1.43. electrons, two 2s electrons, and five 2p electrons.
(a) C–H bonds are considered to be covalent, although (c) As indicated in Figure 1.10, carbon has two 1s
they do have a very small dipole moment, because there electrons, two 2s electrons, and two 2p electrons.
is a small difference in electronegativity between carbon (d) As seen in SkillBuilder 1.6, the electron
(2.5) and hydrogen (2.1). Despite the very small dipole configuration of a nitrogen atom is 1s22s22p3
moments associated with the C–H bonds, the compound (e) This is the electron configuration of chlorine.
has no net dipole moment. The carbon atom has
tetrahedral geometry (because it has four bonds), so
the small effects from each C-H bond completely cancel 1.45.
each other. (a) The difference in electronegativity between sodium
(0.9) and bromine (2.8) is 2.8 – 0.9 = 1.9. Since this
(b) The nitrogen atom has trigonal pyramidal geometry. difference is greater than 1.7, the bond is classified as
As such, the dipole moments associated with the N–H ionic.
bonds do not fully cancel each other. There is a net
molecular dipole moment, as shown: (b) The difference in electronegativity between sodium
(0.9) and oxygen (3.5) is 3.5 – 0.9 = 2.6. Since this
difference is greater than 1.7, the Na–O bond is
classified as ionic. In contrast, the O–H bond is polar
covalent, because the difference in electronegativity
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*** START OF THE PROJECT GUTENBERG EBOOK BIOGRAPHICAL

CATALOGUE OF THE PORTRAITS AT PANSHANGER, THE SEAT OF
EARL COWPER, K.G. ***
ARISE ✤ PRAY ✤ WORK
BIOGRAPHICAL CATALOGUE
OF THE PORTRAITS AT PANSHANGER
THE SEAT OF EARL COWPER, K.G.

BIOGRAPHICAL
CATALOGUE
OF THE PORTRAITS
AT PANSHANGER
THE SEAT OF
EARL COWPER, K.G.
✿
‘A true delineation, even of the
smallest man, and his scene of
pilgrimage through life, is capable of
interesting the greatest man; for all
men are to an unspeakable degree
brothers, each man’s life a strange
emblem of every man’s, and human
portraits faithfully drawn are, of all
pictures, the welcomest on human
walls.’ Carlyle.
LONDON: ELLIOT STOCK
1885.
TO
FRANCIS LORD COWPER

AND
KATRINE CECILIA HIS WIFE,

The Light of her Home,
THESE PAGES ARE AFFECTIONATELY INSCRIBED
BY
MARY LOUISA BOYLE.
Michaelmas 1885.
PREFACE
In the Biographical Sketches contained in this volume, I have

pursued the same system as in my two former Catalogues, of the
Galleries of Hinchingbrook and Longleat,—devoting especial
attention to the immediate members, or to personages in any way
connected with the family in question. In the historical characters, I
have purposely made the details of public and official life (which are
elsewhere recorded) subservient to those of a private and domestic
nature, although it is obvious that in some cases the two cannot be
disentangled. In fact, I have preferred painting my portraits in the
costume worn at home, rather than in robes of office and suits of
armour. I have refrained from mentioning the innumerable
authorities to which I have had recourse, in the British Museum and
other Public and Private Libraries, from a dread of adding to the
weight of a volume already, I fear, too bulky. For help in my labours,
I am indebted to the noble owner of Panshanger himself, for the
able papers on Charles James Fox, Lord Melbourne, and the brothers
De Witt,—while the author of that delightful memoir, ‘Fifty Years of
my Life,’ so well known to the reading public, contributed the
interesting sketch of his ancestor, the first Earl of Albemarle.
The good services of Mr. Elliot Stock procured me the assistance of
Monsieur Charles Rueles, the learned Keeper of Manuscripts in the
Royal Library at Brussels, when at a loss for information regarding
the Marquez de Leganes, a commander little spoken of by English
writers. On the kindness of friends my impaired sight has compelled
me to rely for details of dress and descriptions of many of the
portraits, and, on this account, my especial thanks are due to a fair
member of the Cowper family. In other respects, the work, it may be
‘a poor thing, is mine own,’ and, although in some respects arduous
and difficult, I have found it on the whole an undoubted labour of
love.
M. L. B.
Michaelmas 1885.
GALLERY.
GALLERY.
No. 1.
HENRI DE LA TOUR D’AUVERGNE, VICOMTE DE TURENNE.
Equestrian Portrait, full size. Mounted on a dappled charger. Buff

jerkin. Ruff. Embroidered sleeves. White scarf. Plumed hat.
BORN 1611, KILLED IN ACTION 1675.
By Rembrandt.
E was the second son of the Duke de Bouillon, by Elizabeth

of Nassau, daughter of William the Silent and Charlotte de
Montpensier. De Bouillon was attached in early life to
Henry the Fourth, King of France and Navarre, who spoke
of him as ‘my lieutenant, my friend, and comrade.’ The
Duke was a soldier, diplomat, politician, and man of letters; and,
moreover, founder of the Academy at Sedan, which became the resort
of all the youthful nobility and chivalry of Europe.
The Duke was one of the chief leaders of the Calvinistic party, and
in their tenets he brought up his two sons, the Prince de Sedan and
the Vicomte de Turenne. When the education of the elder was
completed, he went to Holland to learn the art of war, under his uncle
Maurice, Prince of Orange, while Henry continued his studies at home.
In early childhood his constitution was far from robust, which inclined
the Duke to destine him for some civil employment; but the little
Vicomte had set his whole heart on being a soldier, and he was
resolved to prove to his father that the decision he had come to was
ill-founded. He took, in consequence, rather an ingenious method of
manifesting his health and strength. One evening the boy contrived to
elude the vigilance of his governor, who spent hours of anxious
search, and never discovered the truant till the next morning, on the
ramparts of the town. On the carriage of a cannon, where he had
passed the whole night, lay the little fellow, smiling in his calm sleep
over the dreams which had visited his iron pillow,—visions, in all
probability, of the daring exploits of some of his beloved heroes of
antiquity, or some brilliant foretaste of his own future glory. But a still
more characteristic anecdote is told of Turenne’s boyhood. He took
great delight in lecturing, as it were, to a group of admiring listeners,
on the merits of his favourite historian, Quintus Curtius, or the mighty
deeds of Alexander the Great. In such moments his eye would kindle,
his whole face brighten, and he would overcome that hesitation of
speech under which he laboured in calmer moments. One eventful day
an officer (of mature years), who was in the company, ventured to
speak disparagingly of Henry’s favourite historian, and even to
question his veracity! This was too much for the impetuous boy; he
waxed wroth, and answered the attack with indignation, to the infinite
amusement of his mother, who was present. She made a sign to the
officer to prosecute the argument, till the Vicomte de Turenne, with all
the offended dignity of his ten years, left the room in a towering
passion, and the same evening challenged the officer to mortal
combat. The ‘cartel’ was carried to the Duchess, who was much
delighted with this early development of her son’s military ardour. The
challenge was of course accepted, the place of rendezvous settled,
and thither the small hero hastened the next morning, ‘his soul in
arms, and eager for the fray.’ To his surprise he found his mother on
the ground, and the officer by her side, while on the green turf at their
feet was spread a goodly banquet. The Duchess advanced with a
smile, and embracing her son told him she had come to act as second
to his antagonist, but that they must first breakfast, upon which the
three sat down, together with the gentlemen of the hunt, who were
also there assembled, and during the repast, as may easily be
believed, peace was concluded, the honour of the young firebrand
appeased, and an exhilarating gallop put an end to all discord.
Henry was only twelve when his father died; he remained a year
longer at home, during which time he showed a far greater taste for
athletic and military exercises than for sedentary studies; above all, he
delighted in horsemanship, and the more unmanageable the steed,
the more willingly would Henry mount it. Hearing that the Comte de
Roussy (afterwards his brother-in-law) had brought a charger from
Paris that was considered wild and vicious, he never rested till he had
it saddled, and leaped on its back, in spite of the expostulations of the
whole household. In a short time the juvenile Alexander returned from
his triumphant ride, having tamed the modern Bucephalus! When
thirteen, the Duchess sent him to join his brother at the Court of the
Stadtholder; Maurice received him graciously, but insisted on his
entering the army as a private soldier. The Prince died a very short
time after Turenne’s arrival in Holland, but the youth had already
imbibed those lessons of military tactics, and that reverence for
discipline, which, added to his own talents and aptitude for the
service, stood him in good stead his life long. Henry Frederic,
Maurice’s successor as Stadtholder and commander-in-chief, continued
his protection to Turenne, and gave him the command of a regiment
of infantry, which soon became a model of discipline. Under his uncle’s
auspices, the young soldier now commenced active service; in 1629
he distinguished himself more especially at the siege of Bois-le-Duc, a
fortress known as La Pucelle de Brabant.
It is not our intention to make a list of the military exploits of this
great man, whose campaigns in Lorraine, Italy, Germany, etc., would
fill many volumes, and indeed form part of the history of France, or
rather of Europe. While his brilliant victories, his skilful retreats, and,
for the most part, his successful diplomatic negotiations, established
his lasting fame, we shall only enumerate those which are necessary
to a narrative of this nature. In the early days of which we are now
speaking, Turenne’s valour and thirst for enterprise were so
remarkable that Prince Henry Frederic deemed it advisable to
reprimand the young soldier for his rashness, with (it may be
conceived) but ill-concealed admiration for his prowess. The Prince
said one day to some officers who were standing near him, ‘If I
mistake not, Turenne will one day rival our greatest captains in fame
and glory.’ Turenne remained five years in the service of Holland, when
his mother, who had been engaged in political negotiations with
France, sent him to that country, where the King and his Prime
Minister, Cardinal Richelieu, received him most graciously, and gave
him the command of a regiment of foot in the French army. At the
siege of La Motte he mounted the walls in person, and carried the
bastion, for which he was rewarded with the bâton of a field-marshal
—a grade only second to that of Marshal of France,—being an honour
almost unheard of for a young man of three-and-twenty. His humanity
was equal to his valour. During the privations and hardships of the
retreat from Mayence in 1635, the Marshal exerted himself to the
utmost to alleviate suffering. He caused many of the valuable contents
of his own baggage-wagons to be thrown away, in order to provide
room for the weary and wounded; he shared his own provisions with
the common soldiers, consoling and helping all those who were in
need, without distinction of rank or nationality. Never slackening for
one moment in his military duties, which he pursued with untiring
zeal, at the siege of Saverne, foremost, as usual, in mounting the
breach, his arm was struck by a musket-ball, and for some time it was
believed amputation must ensue. The recovery was slow and tedious,
but long before it was complete the Marshal had resumed his duties.
In 1638 he became a lieutenant-general, on being sent to the relief
of Duke Bernhard of Saxe-Weimar, with whom an alliance had been
formed by France. In 1646 he returned to Paris, to the Court, where
the Prime Minister, Cardinal Mazarin, whose recognition of his great
services had hitherto been but lukewarm, was loud in his
commendation, and offered him the Duchy of Château Thierry, and
the hand of one of his beautiful and well-dowered nieces; but Turenne
refused all these offers, from the conviction that some of the
conditions therein involved would prove prejudicial to the interests of
his brother, the Duke de Bouillon, to whom he was warmly attached.
He was defeated by the Comte de Mercy, in command of the
Bavarians at Mariendal, but made a most skilful retreat, and by the
side of the Prince de Condé took his revenge at the battle of
Nordlingen, where Mercy was routed, and received his death-wound.
This brave general was buried near the place where he fell, and his
tomb bore this inscription: Sta, Viator, Heroem Calcas. Turenne then
marched to join the Swedish General Wrangel, the friend and comrade
of the great Gustavus Adolphus, in Hesse, and was preparing for fresh
warfare when the signing of the Treaty of Westphalia gave peace to
Central Europe, concluding the Thirty Years War. A most flattering
letter to the Vicomte de Turenne was written by the Elector of
Mayence, the Duke of Würtemberg, and many other Princes and
Ambassadors, attributing this happy event as much to his military
exploits as to the efforts of the Plenipotentiaries.
France did not long enjoy the blessings of peace for civil war was
now about to shed its baneful influence over the land. Anne of Austria,
the Queen-Mother and Regent (during Louis the Fourteenth’s
minority), was almost entirely under the influence of her Prime
Minister, Cardinal Mazarin, who was very unpopular with the
Parliament and the greater part of the French nation. The successes of
the English Parliamentarian troops over those of the Royalists, and the
downfall of the Monarchy, had given a strong impetus to the anti-
Court party in France, and a faction was formed, well known in history
as the ‘Fronde.’
This nickname was given to the party who were opposed to the
policy of the Queen-Regent, Anne of Austria, and her favourite and
adviser, Cardinal de Mazarin, whose measures they condemned as
unjust and oppressive. One of the principal adherents was the Cardinal
de Retz, or Coadjutor, as he was called, a turbulent and intriguing
spirit; but it soon numbered among its members the most important
and noble names in France. The designation of Frondeurs was given
by a contemporary writer, from the word Fronde,—Anglicè, a sling. He
likened the malcontents to boys who went about the streets slinging
stones, till put to flight by the appearance of any officer of the law. By
degrees the faction assumed a much more imposing form, and though
the name remained, it had certainly lost its significance. Discontent
increased every day, the people clamoured for redress of grievances,
and deputations flocked to Parliament to entreat the interference of
the members against the oppressions of the Court. The Parliament
was divided into three different factions,—the Frondeurs aforesaid, the
Mazarinists, who supported the Cardinal, and the Modérés, who
blamed the ultra views of both parties. Three members in particular
rose up as champions of the oppressed, and so incensed the Queen by
their seditious language, that she caused them to be arrested. This
was the signal for open revolt: shops were closed, streets blocked,
barricades formed, and the liberty of ‘the fathers of the people,’ as
they were called, loudly and insolently demanded. Anne of Austria
showed courage and determination, arguing that compliance would be
a fatal admission of weakness; but the Duke of Orleans and the
Cardinal, alarmed for their own safety and property, overruled her
decision. The captives were released, and the Court departed hastily
to St. Germains, a step which was designated as ‘l’enlèvement du Roi.’
The popular party was triumphant, and the Cardinal de Retz,
considering it a favourable opportunity, exerted himself to gain
proselytes, and the malcontents soon numbered among their
adherents such men as the Dukes de Bouillon, de Lorraine, de
Beaufort, de Longueville, de la Rochefoucauld, and the Prince de
Conti, brother of the great Condé, with many others. They were also
rich in noble female partisans, ‘les héroines de la Fronde.’ Beauty,
birth, and talent swelled the list of the fair conspirators,—
Mademoiselle de Montpensier, ‘la grande demoiselle,’ as she was
called,—the Duchesses de Chevreuse and de Bouillon, the Princess
Palatine, and last, but least in no sense of the word, the Duchesse de
Longueville. When Anne of Austria deserted her post at Paris, a rival in
power, a superior in youth and beauty, reigned for a time paramount
in her stead,—the charming despot of an elective monarchy.
Anne Généviève de Bourbon was at one time so nearly connected
with the fortunes of Turenne that we are tempted to give some details
respecting her eventful life. Her father was Henry, Prince de Condé (or
‘Monsieur le Prince,’ as the head of that illustrious house was always
called), her mother the beautiful Charlotte de Montmorency, daughter
of the Grand Connétable of that name. They were both imprisoned in
the Château de Vincennes, where their daughter was born in the year
1618. Mademoiselle de Bourbon was educated at the Convent of the
Carmelites, where she showed a decided bias towards the vocation of
a recluse, and a corresponding aversion to the idea of a life at Court,
or in the great world. A very short experience, however, of admiration
and success entirely changed her views, and she became one of the
most lovely précieuses of the Hôtel Rambouillet. The cynosure of all
eyes, a crowd of suitors clustered round her, none of whom found
favour in the sight of her parents, till the Duc de Longueville presented
himself. He was her senior by many years, and still under the influence
of a former mistress, the Duchesse de Montbazon; but he came of an
illustrious family, and was not far removed from the rank of a prince of
the blood-royal; and Mademoiselle de Bourbon had the paternal
commands laid upon her to receive him as her bridegroom. At first she
showed the greatest possible repugnance to the marriage, but there
was no alternative; and she walked to the altar, radiant in beauty, and
gorgeously attired, assuming a cheerfulness of demeanour which
belied the feelings of her heart. From that time forward the young
Duchess gave herself up to a system of cold-blooded coquetry, which
had most disastrous results. We quote an eloquent description from
the pages of her biographer, Ville Flore: ‘Un an s’était à peine écoulé,
que la blanche robe de la jeune mariée avait déjà des táches de sang,
et que sans même avoir donné son cœur elle faisait naître
involontairement la plus tragique querelle, oû Coligny perissait à la
fleur de l’âge par la main d’un de ces Guises, auquel elle avoit été un
moment destinée. Prélude sinistre des orages qui l’attendaient.’
Adorers crowded round her, poets sang her praises, novels were
written of which she was the peerless heroine, and still Généviève de
Longueville proceeded on her triumphal march, careless and fancy-
free, making conquest after conquest, creating cabals and jealousies
that became political feuds,—the Court now taking part against, now
with, the beautiful syren. ‘Mais on ne badine pas éternellement avec
l’amour.’
M. de Masillac (or as we will call him by his better-known title, the
Duc de la Rochefoucauld, to which he shortly succeeded), who had
once been loved, and was now hated, by Anne of Austria, laid siege to
the fortress which had held out so long, and carried the heart of the
Duchesse de Longueville by storm. Witty, handsome, cynical, reserved,
and self-contained, with a reputation already established for valour
and intellect, La Rochefoucauld soon gained a complete ascendency
over this daughter of the proud house of Condé.
He was a man who, for the most part, practised what he preached
and expounded in his world-famed ‘Maxims,’ and whose character,
drawn by his own pen, showed how the head preponderated over the
heart in his composition. That he admired the Duchess there can be
no doubt:—
‘Pour mériter son cœur,
Pour plaire à ses beaux yeux,
J’ai fait la guerre aux rois,
Je l’aurais fait aux dieux.’
But his first advances were unquestionably made in cold blood, and it
was in the hope of gaining proselytes to the cause of the Fronde that
he desired the alliance and co-operation of this beautiful woman.
Touched and flattered by the simulated passion of so remarkable a
man, the Duchess gave herself up, heart and soul, to her lover,
obedient to his every wish, submissive to his every direction. She
forgot her pride of birth and position, her marriage vows, and the
tender affection which had hitherto bound her to her elder brother. Let
us hear how the man for whom she made such sacrifices speaks of
her in the early days of their liaison: ‘Ses belles qualités étaient moins
brillantes à cause d’une tâche qui ne s’est jamais vue en une princesse
de ce mérite, qui est, que bien loin de donner la loi à ceux qui avaient
une particulière adoration pour elle, elle se transformait si fort dans
leurs sentimens qu’elle ne reconnaissait point les siens propres.’ And
so he despised the very quality for which he had wooed her,—a
palpable moral!
Madame de Motteville testifies that ambition had little part in
Madame de Longueville’s proceedings. She was only ambitious for her
lover,—‘qui étoit peut-être plus intéressé qu’il n’était tendre.’ Among
her proselytes she gained over her younger brother to the cause; her
husband also was nothing loath to join the Fronde. But La
Rochefoucauld, when he thought to win the great Condé through the
medium of his sister, had reckoned without his host. Madame de
Longueville used all her powers of persuasion, vainly appealing to the
tender memories of home and childhood, but Condé was implacable.
He upbraided his sister with her dishonour, expressed his aversion to
La Rochefoucauld, and joined the Court at St. Germains, where he
assumed the command of the troops that had remained faithful to the
King, and shortly afterwards marched upon Paris to attack the
Frondeurs, who had named his brother, the Prince de Conti, their
‘Generalissimo.’ Now the Duchesse de Longueville had excused herself
from joining her mother, the Princesse de Condé, who was at St.
Germains in attendance on the Queen, on the plea of her approaching
confinement. But the delicacy of her situation did not prevent her
acting under the orders of her despotic lover. She shared all the perils
and hardships of her friends the Frondeurs, assisted at the parades
and reviews of the troops and the civic guard, took part in all the
military discussions, and in fact transformed the Hôtel de Longueville
into a barrack.
In this state of strife and discord both sides concurred in the
advisability of gaining over Marshal Turenne to their interests, and he,
being now in command of the French army in Germany, received the
most flattering letters from the Queen and her Minister. Mazarin was
profuse in his offers of civil and military aggrandisement; renewing the
proposal of an alliance with his richly-dowered niece at the same time
that he complained to Turenne of the disloyalty of his brother, the Duc
de Bouillon.
The Marshal’s answer was manly and straightforward to all these
flattering advances. He wrote respectfully indeed, but said this was
not a moment for men to think of their own personal advancement.
He regretted the disaffection of his brother, and deeply deplored the
troubles that reigned in France; he stigmatised the blockade of Paris
as a most dangerous step, declined with courteous thanks the offer of
the matrimonial alliance on the score of difference of religion, and told
his Eminence plainly that, if he continued to oppress the people, he
(Turenne) could no longer hold out to him the hand of friendship;
moreover, that on his return to France, at the head of his troops
(according to orders from headquarters), he was resolved neither to

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Chapter 1 – Electrons, Bonds, and Molecular Properties 1

WHAT’S IN THIS BOOK

SkillBuilder 1.1 Drawing Constitutional Isomers of Small Molecules

SkillBuilder 1.2 Drawing the Lewis Dot Structure of an Atom

SkillBuilder 1.3 Drawing the Lewis Structure of a Small Molecule

SkillBuilder 1.4 Calculating Formal Charge

SkillBuilder 1.5 Locating Partial Charges Resulting from Induction

SkillBuilder 1.6 Identifying Electron Configurations

SkillBuilder 1.7 Identifying Hybridization States

SkillBuilder 1.8 Predicting Geometry

SkillBuilder 1.9 Identifying the Presence of Molecular Dipole Moments

SkillBuilder 1.10 Predicting Physical Properties

A Common Mistake to Avoid

(b) Begin by determining the valency of each atom that

(d) Begin by determining the valency of each atom that

Alternatively, we can draw four carbon atoms in a linear

Next, the oxygen atom must be inserted. For each of the

There are no other possibilities. For example, placing

1.2. The carbon atoms are tetravalent, while the chlorine

(e) Begin by determining the valency of each atom that

1.5. Aluminum is directly beneath boron on the periodic

(g) Chlorine belongs to group 7A of the periodic table,

(c) Each carbon atom has four valence electrons, and

(e) Each carbon atom has four valence electrons, and

(b) Each carbon atom has four valence electrons, and

1.10. Each of the carbon atoms has four valence

the oxygen atom exhibits only five valence electrons

(i) Two of the atoms in this structure exhibit a formal

(e) Carbon is in group 4A of the periodic table, and it

(g) Oxygen is in group 6A of the periodic table, and it

1.14. Carbon is in group 4A of the periodic table, and it

Oxygen is in group 6A of the periodic table, and it

The nitrogen atom (group 5A) should have five valence

(f) Chlorine is more electronegative than carbon. As

1.16. Oxygen is more electronegative than carbon. As

1.21. The bond angles of an equilateral triangle are 60º,

(b) Each of the highlighted carbon atoms (below) has

(d) Each of the two central carbon atoms has two

(e) One of the carbon atoms (the one connected to

1.30. The silicon atom has four  bonds and no lone

(h) Each C=O bond has a strong dipole moment, and in

(i) Each C–Cl bond has a dipole moment, and they do

(l) Each C–Cl bond has a dipole moment, but in this

1.32. Each of the C–O bonds has an individual dipole 1.35.

To determine if these individual dipole moments fully

(d) The carbon atoms are tetravalent, while the chlorine

The chlorine atom can be placed in any one of the six