PSU Student Textbook Reviews
William H. Brown and Christopher S. Foote
Organic Chemistry, 2nd Edition, Saunders College, 1998
Ch 8 - Substitution/Elimination
Ch 17 - Aromatic Substitution
Ch 20 - Carboxylic Acid Derivatives
Ch 21 - Amines
(Most of the student comments about Brown and Foote were integrated with those about the other five authors. These combined comments can be found at the ends of the other authors' entries, as well as inextricably intertwined with many of the other entries.)
Brown and Foote
LIKED: Clear and relevant tables, definitions in the margins,
chapter summary, key reactions at the end of the chapter, chapter
problems (within text) with solutions.
DIDN'T LIKE: What felt like an absence of certain important mechanisms.
Whether or not the mechanism was a need-to-know, seeing it ALWAYS
helped me understand what was going on a little better, and I
would go so far as to say was crucial in trying to "think
like a molecule."
Brown and Foote
LIKES: I really liked the idea that there were example exercises
after each basic idea in this book and the fact that it came with
a model kit, CD and electrin pushing book.
DISLIKES: There were way too many mistakes between the solutions
manual and the book! The editor should have been shot! It also
could have had some more examples and homework problems that were
more up to Dr. Wamsers speed (naming and reaction problems). Doing
homework problems only got one up to a certain level. This book
needed problems from basic to really hard.
Brown & Foote (Ch 8)
Again very similar to Solomons. I like the fact that Brown
& Foote offer a summary of information which is very clear
and fairly well organized at the end of the chapter. Also the
blue box at the end of the chapter is a very good method for outlining
the important reactions in chapter. I would say that the reactions
at the end of the chapter are about the only thing in Brown &
Foote which are clearly presented in each chapter and is one of
the only things I like about Brown & Foote.
Brown & Foote (Ch 8)
The following are things that I did like:
1) I feel that this chapter was written with extraordinary organization.
Each type of nucleophilic substitution was given its own section,
and the information was presented very clearly. The same is true
for the elimination reactions. In comparison to Wade, Brown and
Foote was able to cover that same exact information in almost
half of the amount of pages.
2) Section 8.6 provided several examples of nucleophilic substitution.
These examples are extremely helpful to students.
3) At the end of the chapter there is a section called substitution
versus elimination. These short, concise paragraphs were great
summaries.
4) Table 8.13 serves as a great reference.
5) There are sample problems with solutions in nearly every section.
The following are things at I did not like:
1) In comparison to Wade, there was nothing that I did not like
about this Brown and Foote chapter. I will discuss this more in
the following reviews.
Brown & Foote (Ch 8)
Not nearly as comprehensive an explanation as Jones. Some
explanations very hard to follow i.e neighboring group participation,
phase-transfer catalysis.
Text seems to jump around a lot. Lots of holes!
Brown & Foote (Ch 8)
Likes
-The use of experimental evidence/ theory behind reaction mechanisms
-Detailed summary of substitution versus elimination reactions
in table 8.13
-Use of beta elimination terminology
-Neighbor group participation
Dislikes
-Limited use of ball and stick diagrams
Brown & Foote
Likes
-Highlighting (yellow box) substiuent of interest
-Chemistry in action boxes
-Comprehensive table of physical properties
-Well illustrated molecular orbital diagrams
Dislikes
-Minimalistic approach to "Key Reactions" table at
end of chapter, movement of electrons would be helpful
Brown & Foote (Ch 8)
Likes:
The "Mechanisms" boxes shows how the reactions takes
place and the step by step captions explains what is happening.
Good section on protic and aprotic solvents.
There are "Example 8.X" coupled with a "Problem
8.X", that are very similar to each other. The example problems
lets you check your answers without having to break the flow of
the reading by going to the solution manual.
The "key reaction" section at the end of every chapter
is a convient collection of the key reactions. Also each reaction
notes the section in which the text discusses that particular
reaction making it easy to refer to that particular section.
Dislikes:
Weak on the discussion of leaving groups. Ege does a better job
on what makes a better leaving group and on how to make better
leaving groups.
Brown & Foote (Ch 17)
Likes
-Use of reactivity figure 17.4
-Extensive nomenclature section, including lactams and imides
-Use of colored arrows for electron pushing
-Complete listing of reactions at end of chapter
-Highlighted box of atoms of interest in reaction diagrams
Dislikes
-Grouping by reaction type
-Less detailed reaction steps
Brown & Foote (Ch 17)
Incomplete nomenclature section (as in all of Brown &
Foote) with sporadic examples, no real rules laid out: very sketchy.
Reactions mixed in on both sides of spectroscopyconfusing
layout.
Interconversion of functional derivatives section was pretty weak.
And I really dislike those 2 page "Chemistry in Action"
sections that disrupt the flow of the text. Besides, who has time
to read them in Organic Chemistry? If they are optional, I would
guess very few students read through them: there's already too
much information!
Brown and Foote (Ch 17)
Of course, since we have read 20 chapters of this text, it
is easier to "get a feel" for the whole book, and a
little difficult to criticize the other texts based on only two
chapters. However, the following is how I feel about this chapter.
I think that this chapter is a little too long, and should be
divided into two chapters. The first chapter should cover the
reactions of only oxygen-based molecules, and the second chapter
should cover the reactions of nitrogen-based molecules and other
atoms. Also, there are not enough nomenclature examples, and sometimes
the explanations for the nomenclature are not clear.
Brown & Foote (Ch 17)
The following are things that I did like:
1) The various types of reactions were highly organized in the
following format:
Reactions with Alcohols
Acid Halides
Acid Anhydrides
Esters
2) Several example problems.
3) Mechanisms are clearly separated into boxes and they include
specific information about the reaction.
4) Includes table describing IR absorptions for all of the carboxylic
acid derivatives, and actual spectras showing the actual peaks.
The following are things that I did not like:
1) Section on interconversion of functional derivatives includes
a figure that I am still trying to understand. Unfortunately,
the interconversions were not displayed very well.
2) Not near enough nomenclature examples and problems.
Brown & Foote (Ch 17)
I wish that Brown & Foote offered more reaction mechanisms
in the boxes in the reading rather than just one line explanations.
The reactions are sometimes easier to remember if I have a reaction
mechanism that explains the process. The reactions in the blue
box at the end of the chapter is a life saver.
Brown and Foote (Ch 20)
The layout is easy to follow, and the repetitiveness of the
order of the text is great. In other words, a student reading
this text always know that most chapters dealing with functional
groups proceed in the following order: nomenclature, followed
by physical properties, followed by mechanisms etc. While the
graphics are sometimes packed with information, it is better than
some of the charts and tables from the other textbooks, which
supplied little information. This book also has a great summary
of key reactions at the end (the only text which does this!) which
is helpful. I like the sample questions that it has, as well as
how all of the mechanisms are in blue boxes.
The only downfall of this book is that sometimes I feel that it
skips explanations, and only when I consult the study guide and
your notes do I get a more complete picture of what is going on.
It never highlights or italicizes key ideas, and sometimes fails
to explain certain things even though there are questions in the
back which pertain to it. For example, there was a question regarding
how naphthalene undergoes substitution, but there was no reference
in the book as to why and how naphthalene reacts. Therefore, not
until I am confronted with a question of how something reacts
the way it does, that I realize that it even does this.
Brown & Foote (Ch 20)
The following are things that I did like:
1) Overall I feel that this is the best chapter that I have read
in Brown and Foote!
2) Each section is very clearly written and includes detailed
mechanisms.
3) The explanation for the theory of directing effects was very
effective.
4) Without Table 20.1, I would have had a much harder time learning
the effects of the various substituents.
The following are things that I did not like:
1) There were not enough example problems accompanying the nucleophilic
aromatic substitution section.
Brown & Foote (Ch 20)
Weak explanation of o,p vs. m-directing theory relative to
Jones, but compared to other B & F chapters, this one wasn't
so bad. Good organization. Some of the problems in the back of
the chapter (in fact, lots of them) seemed pretty far afield from
the major points made in the text.
Brown & Foote (Ch 20)
Likes
-Passage on theory of directing effects/activating-deactivating
-Table of directing/activating substituents
-Potential energy diagram (fig 20.1)
Dislikes
-Lack of clear section on effects of multiple substituents
Brown & Foote (Ch 21)
Brown & Foote seem to ramble from topic to topic with
weak organization of material.
Brown & Foote (Ch 21)
The following are things that I did like:
1) Great explanation of the classification of amines, showing
how it differs from classifying carbons.
2) The section on pyramidal inversion was very clear. Plus the
diagram that they included were very helpful in understanding
the conversion from sp3 to sp2 and back to sp3.
3) The separation and purification charts were very helpful in
understanding the properties of amines in the real world.
4) Diagram on page 862 for primary aromatic amines was a great
summary and very useful for planning ahead for what I was about
to read.
5) Example problems were complex and helped to prepare me for
the exam.
The following are things that I did not like:
1) Again, not enough nomenclature examples and problems.
2) The various preparations of amines were only listed. I think
that there should have been a short review instead of having to
flip back to previous chapters.
3) I found it confusing that both HNO2 and NaNO2, HCl were used
in the reactions. For me, I do better learning one method. However,
once you explained it in class it made much more sense.
Brown & Foote (Ch 8 and Ch 20)
Likes - Very nice page layouts, and the appendixes and summaries
are very nice. I like the Chemistry in action boxes, I really
like to see applications of what we learn.
Dislikes - I would like to see some more medical uses of chemicals
in the book, but it is still a very good book. The CD that was
included in our edition was not overly useful, mechanisms, like
the ones in class would be helpful. The program that you use in
class is very nice for mechanisms. Well that is all of the books,
my choice for next year would be Solomons' book, I thought that
it was very well done and the CD included sounded like it had
a lot of very useful information on it.
Brown & Foote (Ch 8 and Ch 20)
1)Layout of text: B&F is very easy to read and has pretty
good graphics throughout. The ease of use is one of its best dimenstions.
2)Clarity: The text of B&F doesn't screw aroundthey hit
you with the info straght up.
3)Logical flow:sometimes I feel like B&F presents topics and
then skirts the issue and then will re-present it later in the
book. The problem is that I found myself usually ignoring it the
first time when it would have been helpful to know it originally.
They should always only assume that we know as much as we have
done to that point, Ex. Phenyl and benyl subsituents appear throught
but we don"t hit them until chaptr.19. 4) Overall: I really
like B&F. I feel its text is straight up and gives me what
I need to know. The graphics are good (although not like Carey)
and, for the most part, the whole book compliments text and graphics
nicely.
Brown and Foote (Ch 8 and Ch 20)
A. I think the presentation of mechanisms is a strong point
for this textbook - it is an important aspect of O Chem and was
justly treated so by B&F. I also appreciated the fact that
the definitions of terms were presented on the side of page and
not in the actual text which, to me, seemed to weigh down the
flow of the text. The photos were both interesting and applicable
- they offered some latitude to the information being presented
and added some eye-appealing color to the pages.
B. The graphics were not as well presented as with the Wade text.
I wish the summary at the end of the chapters were not in paragraph
format - we've just read a chapter full of paragraphs - present
in information in a "cleaner" way - i.e. glossary or
specific examples.
Brown and Foote (Ch 8 and Ch 20)
In Chapter 8 of Brown&Foote's textbook, they present new
concepts and reactions with a logical approach beginning with
explanations about basic Nucleophilic Aliphatic Substitutions
to leaving groups to Eliminations at the beta position. Giving
explanations about the Kinetic and Regioselective properties of
each type of reaction give a thorough description of how a chemist's
mind would process the information. The presentation throughout
the chapter is clear and right-to-the-point giving general examples
which can be applied and used in learning the new reactions. I
really like how Brown&Foote give an example question and solution
before the actual question to which the answer must be looked
up in the solution manual. Giving an example question and solution
shows a student how the authors think a reaction or synthesis
should be done and gives guidelines in doing similar problems.
Chapter 20 gives a presentation on Aromatics II: Reactions of
Benzene and Its Derivatives. Each type of reaction is given with
mini reactions showing how the electrophile is derived from the
reagent used (e.g. Cl2 + FeCl3 == Cl+ FeCl4- ) The more basic
reactions and Di/polysubstitution reactions are explained thoroughly,
discussing the substituent effects resulting by various groups.
There are a good amount of examples in between breaks of texts.
One thing I did not like about Brown&Foote was the omitting
of certain mechanisms (I'm assuming that the omitted mechanisms
are not as important as the concept of a particular reaction).
Brown and Foote (Ch 17 and Ch 20)
A. - Graphics were superior to the Jones text. They seemed
to be displayed with a higher print quality and more were plentiful.
B. Presentation of spectroscopy seemed dull and bulky when compared
to the other text.
Brown & Foote (Ch 17 and Ch 21)
1)Layout of text: the amine chapter in B&F is pretty good
but the carboxyl deriv chapter is a little hard to follow. I had
to read the carboxyl deriv chapter many times before I could understand
all of the reactions and the derivates that it was discussing.
A table would have been really helpful.
2)Clarity: Once again, the amine chptr was good but the carboxyl
deriv chapter suffered. Much of this was due to the layout. 3)Logical
organization: I felt that both of the chapters presented the info
in an easy and progressive fashion that allowed me to build on
my previous knowledge of the topic.
4)Overall: I really didn't like the carboxyl deriv chapter. It
was hard to follow everything that was going on. The amine chapter
though is pretty good.