Chemical Education Today
Book & Media Reviews
Keynotes in Organic Chemistry
by Andrew F. Parsons
Blackwell Publishing: Oxford, UK, 2003. 228 pp.
ISBN 0632058161. $19.95
reviewed by Joel M. Karty
Tendencies of our “fast food society” are increasingly
becoming manifest in chemical education. This is particu-
larly true for undergraduate organic chemistry, largely because
of its perceived difficulty coupled with its importance in ad-
mission to medical programs. Currently, student demand is
incredibly high for that one special recipe—that one special
book—that is short in length and lays out organic chemistry
in a manner that makes the material easy without requiring
much time or effort (i.e. critical thinking and problem solv-
ing) on the part of the students. Publishers have taken ad-
vantage of such demand, offering supplementary texts that
appear to make those promises, even in their titles. But truly
making good on those promises is analogous to fast-food fi-
let mignon—first, it can’t be done, and second, even if it
could, you won’t remember it (or, perhaps won’t want to re-
member it) for very long. Keynotes in Organic Chemistry, by
Andrew F. Parsons may appear to be in that genre of pana-
cea texts, but, in fact, is not. It is a short paperback text—
228 pages, including problem solutions and index—but it
does not promise to make organic chemistry easier. Rather,
as a result of “the trend towards modularization of chemistry
courses,” it attempts to meet “the need for smaller, highly
focused and accessible organic chemistry textbooks, which
complement the very detailed ‘standard texts,’ to guide stu-
dents through the key principles of the subject.”
The title of the book is an accurate description of its
contents. Parsons has successfully distilled an entire 1200 page
textbook to the essentials that a student should take away
from a full year of undergraduate organic chemistry. The or-
ganization of concepts and reactions is similar to that found
in most traditional text books—it begins with structure and
bonding, and later moves on to reactions involving alkyl ha-
lides, alkenes/alkynes, benzenes, aldehydes/ketones, and fi-
nally carboxylic acid derivatives. However, there are two
chapters that stand out and deserve favorable mention. One
is “Reactivity and Mechanisms.” This chapter outlines the
essentials necessary to understand mechanisms, delving into
the factors that govern ion and radical stability and also dis-
cussing steric effects. Furthermore, this chapter provides an
overview of reaction types, and briefly discusses kinetic and
thermodynamic control of reactions. In a book of its size,
one might not expect discussions in these topics. The sec-
ond of those chapters is “Spectroscopy,” in which four of the
most common techniques for organic analysis (MS, UV, IR,
and NMR) are discussed. Doing so in a single chapter may
allow students to better see the complementarities among the
four techniques.
The best use for Keynotes in Organic Chemistry is not
clear. It may be as a review for a course final exam or for a
www.JCE.DivCHED.org • Vol. 81 No. 5 May 2004
standardized exam. The reason is that in Parson’s distillation,
it was done without loss of emphasis on the most important
aspects of organic chemistry—fundamental concepts and
mechanisms. In fact, the majority of the end-of-chapter prob-
lems either directly ask for a mechanism or ask one to use a
mechanism to explain a particular phenomenon. Therefore,
if a student at one time had a solid understanding of organic
chemistry, this text will serve as a good refresher. If, on the
other hand, a student did not leave organic chemistry with a
solid understanding, this text provides an outline of what
should be known and understood, including fundamental
concepts and mechanisms. However, don’t expect Keynotes in
Organic Chemistry to provide a better understanding than a
student attained the first time through the material. It most
likely will not. Instead, the text can allow the student to dis-
cern quickly which reactions/concepts they understand and
which ones they don’t. With this knowledge, they might then
open a traditional textbook to study those areas in which they
are weak. If used in such a manner, this text may also be in-
corporated into a student’s organic chemistry course.
Perhaps the only negative aspect of this text is that, in
many instances, it goes beyond what I would consider to be a
key point. For example, when discussing electrophilic aromatic
substitution reactions, electron donation of Cl, Br, and I sub-
stituents via resonance is said to be weak, due to the poor over-
lap of the 3p orbital of the halogen atom and the 2p orbital of
the C atom on the benzene ring. It seems that in the interest
of simply providing the essential information, the argument
could have been finessed using an electronegativity argument.
In the same chapter, electrophilic substitution reactions involv-
ing naphthalene and pyridine are discussed, whereas the typi-
cal organic chemistry course and the typical standardized exam
do not expect that students have seen them. The same is true
for the benzoin condensation reaction discussed in a later chap-
ter. In the spectroscopy chapter, high resolution mass
sepctrometry is discussed—something that, again, I would not
consider to be a key point. I simply fear that these discussions
that are essentially extraneous for the average organic student
will serve to confuse more than enlighten.
My greatest concern with this text, however, is whether
students will, in fact, use it correctly. I think that a large frac-
tion will not. Most students struggle in organic chemistry,
largely because they rely heavily on memorization without hav-
ing a solid foundation of fundamental principles or a good
understanding of mechanisms. The truth of the matter is that
organic chemistry encompasses such a vast amount of material,
rendering memorization essentially futile. What I envision is
that students will view the text as a shortcut. They will see
that the important material has been outlined, and they will
do nothing more than attempt to use such an outline to
streamline their memorization. If so, Keynotes in Organic
Chemistry will serve to do nothing except provide a false sense
of security.
In summary, Keynotes in Organic Chemistry achieves its
goal of providing an outline of important concepts, reactions,
and mechanisms that is quite complete and well written. It
maintains strong emphasis on fundamental organic principles
and mechanisms throughout, which is somewhat unique for
• Journal of Chemical Education 651
 Chemical Education Today

Book & Media Reviews

a text of its size. If a student uses it correctly, it may be an Joel M. Karty is in the Department of Chemistry, Elon
asset. If not—and I envision that most students will not—it University, 2625 Campus Box, Elon, NC 27244;
may be a detriment. jkarty@elon.edu

652 Journal of Chemical Education • Vol. 81 No. 5 May 2004 • www.JCE.DivCHED.org