Maitland Jones, Jr.
Organic Chemistry, 2nd Edition, W. W. Norton, 2000
Ch 6 - Substitution/Elimination
Ch 13 - Aromatic Substitution
Ch 19 - Carboxylic Acid Derivatives
Ch 20 - Amines
Jones
Things I liked about Jones:
1. Good use of color/graphics
2. Good integration of text with graphics (text explained graphics
as you went along)
3. Good explanation of stereochemistry in ch.6. This concept is
difficult for some new students
4. Excellent end-of-chapter summaries.
5. Good use of "hints" throughout chapters.
6. Good labeling of reactions (with related info)
7. Good analysis of "what you should know so far" within
chapters.
8. Problems throughout chapters seem to be more linked to potential
lab problems, and more conceptual in nature. Give you a feel for
the "big picture".
9. "Common Errors" helpful
10. chapters seem more interrelated due to crossover of examples
used.
Things I didn't like so much
1. some of the writing is a bit "hokey", but it's better
than having an overly dry o.chem text.
2. Table of subst. effects on further electrophile substitution
wasn't as clear as B & F.
3. Kind of difficult to pick out reactions for flashcards, forced
to use end-of-chapter list.
4. not as much on analytical tools (IR, NMR, etc) within chapters.
5. Still uses cyclohexene with inner circle for benzene ring in
examples. Makes it more difficult when doing reactions to visualize
where things came from.
Jones
LIKES:Not really any.
DISLIKES: Again, like Ege, there aren't helpful graphics, or if
there are they are few and far between. B & F had tons of
"boxes" or inserts talking about different things happening
with chemistry in the world along with Carey. This text didn't
have any.
Jones
Likes: very clear and organized. And the aramtic chapter was
before the carboxylic chapter, so I liked the way it was organized.
I liked the examples they give in the chapters, and the structures,
help to visualize the reaction better.
Dislikes: the carboxylic chapter was a little too long, and it was a little hard to follow.
Jones //Brown and Foote
To sum up, Jones has a very chatty, wordy style but takes
the time to lead the reader from step A to step B every time,
while Brown & Foote often left me wondering how they'd drawn
a certain conclusion. The Brown & Foote "Summary"
section is very weak, as if it was the last, exhausted attempt
to finish up the chapter without really helping the student in
any real way. I like their "Key Reactions" sections
at the end of the chapter, but that's about it. I found this text
very frustrating: poorly organized, incomplete, illogical in places.
And the workbook problems often didn't correlate well, either.
Jones, in contrast, is incredibly complete, thorough, and student-friendly.
I like the general case/specific example format, the common errors
section and the synthetic potential sections. Besides the chatty
style, I think it would be an outstanding text.
Jones (Ch 6)
The Jones book made great use of graphics, and looks like
it has a very complimentary CD. The book is very personal, wanting
to work through O.Chem with the reader. A lot more real life situations
as far as labs go, and the usefulness for certain reactions. Seemed
to go a lot more indepth speaking of HOMO, and LUMO, as well as
the rate law. Together, this would be very complimentary to P.Chem.
This book has great captions explaining every little detail about
orbitals, and transition states. Good job explaining SN1, and
SN2 reactions. Sometimes a little too much info at once, which
may overload the reader. Most of the homework problems were interspersed
in the reading, which was good, but I felt that the book needed
more homework problems at the end of each chapter.
Jones (Ch 6)
Very thorough with lots of good explanations/graphics on molecular
orbital theory.
Good nomenclature chart.
Nice treatment of acid-base chemistry, arrow formulism, etc.
Smooth transition from theory to examples.
Jones (Ch 6)
Things I liked:
In the Jones book,I found the frequent illustrations to be very
valuable. Everything in the illustrations is carefully labeled
and pictured as it is described in the text. There are not as
many illustrations in Brown and Foote. The author of the book
is very easy to follow, the writing style is humanistic, instead
of dry and robotic, as Brown and Foote feels to me. Jones' book
uses the authors personal experiences to illustrate points, which
is nice.
Things I didn't like:
The chronological order of the Jones book material seems messy.
Concepts seem to jump around instead of
Jones (Ch 6)
WHAT I LIKED:
1) HOMO/LUMO INTERACTIONS
2) POTENTIAL ENERGY DIAGRAMS THROUGHOUT THE CHAPTER
3) EXPLANATION OF SOLVATION/ROLE OF SOLVENT
4) THE SAMPLE FILE CARDS FOR STUDY WITH INDEX CARDS 5)COMMON ERRORS
SECTION VERY UNIQUE AND HELPFUL.
WHAT I DIDN'T LIKE:
NO COMPLAINTS.
EXCELLENT CHAPTER!
Jones (Ch 6)
Jones' text presentation is too "dry" in presentation
and style. There is no appeal and visual helpfulness in graphics.
All compounds are drawn as carbon skeletons and do not seem to
bring a student to the modern-time thinking/visualizations. Layouts
are not easy to follow and Jones suddenly splits the page into
two sections and are hard to follow. The overall presentation
and usefulness of Jones' text seems too two-dimensional in all
respects.
Jones (Ch 6)
Reasons and comments:
There was no index;
References to CD rom illustrations +;
Clear tables with nucleophilic strengths/basicity in solutions;
Problems, but no solutions, which is a minus because it doesn't
allow you to check knowledge before continuing reading, unlike
B&F;
Clear figures of SN1/SN2, efficiently presented;
Reactions are shown as a "general case" along with a
"specific example" +;
Syntheses section in back that is included in summary is a very
nice and clear illustration of the important and highlighted reactions
in this chapter;
There don't seem to be a lot of additional practice problems -;
Graphics are well presented with good explanations and transition
state illustrations;
Should have a separate section for 6.8 that pertains mostly to
biochemistry/biology;
Good illustrations of Newman projections, good review;
Alkyl halides section includes Bronsted, arrow formalism, lewis
acid/bases, HOMO/LUMA, which should be in a different chapter,
like in B&F;
In text, questions are asked and answered that keeps students
more involved when reading;
No separate sections for Hoffman/Cope elimination;
No clear explanation of SN2 versus E2 or SN1 vs. E1.
Jones (Ch 6)
Jones has good advice in the intro to the chapter (page 208).
It has great graphics and the tables on pages 229 and 232 are
especially helpful in learning about nucleophiles and leaving
groups. Jones also has a good size font and the use of color prevents
eye strain after hours of reading.
Jones (Ch 6)
Great introduction, much better than Brown and Foote. Sometimes
introductions sound like they were put there just because style
dictates it, but the introduction for chapter 6 in Jones
puts the chapter's subject in perspective. Its tone is very encouraging,
and it even offers some good advice.
There is a good progression of presentation. The wording easily
leads from one section to another, unlike Brown and Foote and
some other texts which just seem to throw in sections haphazardly.
There is good color coding. Problems are highlighted in green.
Atoms are highlighted so that their movement in mechanisms is
easily traceable. Color is used to help us visualize steric hindrance
also.
As in chapter 20, the homework problems seem much more useful.
My only concern for this chapter is that Jones is already
discussing the HOMO and the LUMO, which are still difficult concepts
for me. I mean, I could give you the definition, but I don't quite
have a grasp on it yet. So I wonder if chapter 6 is a little early
to be talking about these concepts. On the other hand, if I had
had a more in depth introduction to orbitals, HOMO, and LUMO earlier
in our text maybe I would have a better grasp on it now.
leading into each other. Brown and Footes text is better in terms
of bridging the road from topic to topic.
Jones (Ch 13)
Excellent explanations of mechanisms and resonance.
Leads you through step-by-step.
Excellent, complete diagrams.
Much better explanation of o,p vs. m-directing substituents.
No jumping from A to C while neglecting B as Brown & Foote
often does.
Jones (Ch 13)
Great captions, but do not like they way they introduced resonance.
The captions helped to highlight the mechanisms just like Brown
and Foote. I really like the way the synthesis problems were grouped
together to show the reader that there are several ways to do
a similar synthesis, and to be creative. Once again, this book
gives a lot more life involving lab techniques, and uses for the
synthesis problems. This chapter was very descriptive. Both books
did a nice job in showing resonance forms, and the Jones book
went a step further to make note of the poor resonance structure
when N gets a 2+ charge and is too high in energy (Love those
captions) (As I recall, I got this information from your lecture,
not the book). Information is a little sporadic, but a lot more
info than Brown and Foote(this can be looked at as both good,
and bad!!)
Jones (Ch 13)
This chapter had numerous complications, beginning with the
tone of the writing. With words such as " hopes" "disappointments"
and " magic" the target audience appears to be children
and not college students. On page 601, a chlorine atom is "plucked"
(why that terminology is used remains a mystery). The writing
is both unprofessional and too wordy. There is a section discussing
the author's chemical brothers, which is simply fascinating, but
irrelevant to the material. There are no tables presented, and
the mechanisms are not highlighted in any way. The mechanisms
are too condensed, colorless, and difficult to find.
Jones (Ch 13)
WHAT I LIKED:
1) POTENTIAL ENERGY DIAGRAMS
2) COMMON ERROR SECTION
3) IN CHAPTER SUMMARY REVIEW OF LEARNED BENZENE REACTIONS
4 ) SUMMARY AT END VERY HELPFUL.
WHAT I DIDN'T LIKE:
1)MECHANISMS NOT AS CLEAR AS IN B&F.
Jones (Ch 13)
Reasons and comments:
No index;
Graphs are well indicated by additional molecule drawings/ colors;
Introduction should have been more emphasized on halogenation
etc (major reactions in chapter), not Energy diagrams;
Delocalization of charges/resonance energy explained clearly,
just like in class, unlike B&F (also uses analogies such as
valleys/mountains); B&F has no real clear explanations of
why a particular resonance structure is unstable or stable (only
in homework);
Diels-Alder reaction was introduced too soon; should have been
presented in the conjugate dienes chapter like in B&F;
Alerts were well pointed out;
Good illustrations of positive delocalization of charges, I think
that B&F really lacks those pictures.
Halogenation, nitration, sulfonation should have been introduced
first;
Friedel-Craft acylation: review of acyl groups +;
Jones is lacking step-wise mechanisms;
B&F lacks more information of benzynes; Jones does a better
job explaining with additional molecular orbitals;
Summary of syntheses was well divided, but lacks brief explanations
like in B&F;
Summary of simple aromatic substitution: "what we can do
so far" is a very good review of reactions of some previous
chapters as well;
Table 20.1 from B&F is more clear compared to Table 13.1 in
Jones;
Energy diagrams of ortho, meta, para substitution +;
Information of inductive effects in aromatic substitution (polarization)
+;
Overall, this chapter seems very reaction-oriented; it includes
some very good examples of reactions (especially section 13.12
polysubstitution and synthesis of multiply substituted benzenes),
just like in lecture.
Jones (Ch 13)
Things i liked:
Again, in the Jones text, i found the illustrations to be valuable.
I feel that Brown and Foote do not include enough illustrations.
Things i didn't like:
It seemed to me that the Jones book made the material more confusing
in this chapter than did Brown and Foote. The Organization of
material was poor, and the mechanisms were not described with
as much clarity as in Brown and Foote.
Jones (Ch 19)
WHAT I LIKED:
1) ENOLATE CHEMISTRY IN SAME CHAPTER
2) MECHANISMS WERE CLEAR
3) SUMMARY AND COMMON ERRORS VERY HELPFUL.
WHAT I DIDN'T LIKE:
1) I PREFER LOOKING AT EACH REACTION WITH EVERY GROUP AS ONE ENTITY.
THIS IS DONE IN B&F.
Jones (Ch 19)
Commentary:
In general, Jones' text appears to focus on the concepts. The
book challenges the reader to think critically, to apply knowledge
learned in previous chapter to similar but new reactions. The
student learns mechanisms by trial and error. In theory, Jones'
text has an admirable philosophy, but I would prefer to get it
right the first time before being aware of the potential erroneous
methods. On the other hand, Brown & Foote focuses on detailing
mechanisms or bluntly noting the similarities between mechanisms.
So the first exposure to a mechanism will be the correct method.
Specifically, Jones' method of instruction for this chapter seemed
almost random. The techniques of showing reaction maps, mechanisms,
or charts were not consistent throughout.
Things I like:
I liked the presentation of this text. The introductory quotes.
The book isn't as intimating, in appearance, as Ege. There is
alot of white space along the margins and between the text and
its graphics. Information doesn't appear to look too compressed
within a page. The use of colors also help to delineate text sections
from mechanisms and problems.
I liked the fact that the first functional group, acid halides,
was introduced with a reaction map before going into detail about
them. It was a pity that the following functional groups didn't
have this device to introduce reactions
Things I didn't like:
Unlike our current text, there were many examples of nomenclature
at the beginning of this chapter. This led me to expect detailed
mechanisms in the following pages. I found very few mechanisms.
Most were in the form of homework questions such as the transesterification
mechanism. It is tedious to look for a mechanism in a study guide.
Oddly, the chapter summary was a series of tables without much
organization or introductory text. It didn't appear to link similar
reactions with the various functional groups. Each group had its
own table, but a cross-referenced chart would have been more useful
for this chapter. Our current text does a much better job of linking
the similarities among the functional groups with section 17.10
"Interconversion of Functional Derivatives".
Jones (Ch 19)
Defines "acyl" right up front in a way that is easy
to picture (Brown & Foote neglects basic definitions, often.)
Good nomenclature section.
Good graphics e.g. Fig. 19.23.
Very logical presentation.
So easy to read!
Jones (Ch 19)
This chapter has lots of examples. This is great, and once
again, this book delivers a lot of info at once (ketene=new stuff).
Just like the synthesis problems, really good how they show a
lot of similar info on one page, however, this may discourage
some students. Both books were similar in how they show the purpose
of the functional derivatives of carboxylic acids, and the Jones
chapter was healthier due to more problems being interspersed.
One thing I found that Brown and Foote does, is cut back on full
mechanisms, and electron pushing as the chapters increase. I suppose
this is why a complimentary book, "Pushing Electrons"
accompanies it. But Jones does not cut back, and still shows full
mechanisms, and electron pushing. This constant battering of similar
movement of electrons can only benefit students, especially those
that have trouble with mechanisms. The book keeps up with the
little captions everywhere, which helps the reader to remember
the little things learned from previous chapters and build on
that. Some of the info was again a bit too cluttered, which may
discourage some students.
Jones (Ch 19)
Even though only 30 pages pertained to this topic, 72 pages
for any one chapter is too long. This text did not highlight its'
chapters in any way, causing a student to search for the mechanisms.
Even when a student did find them, they were not clear. Again,
there was not enough room in the margins.
The only good part of this text was the nomenclature discussion
showing the conversions from systematic to common names for the
acid halides. The fact there was both "general case"
and "specific examples " for the mechanisms was helpful.
Jones (Ch 20)
WHAT I LIKED:
1) NOMENCLATURE MUCH CLEARER THAN B&F
2) ALKALOID SECTION
3) PHASE TRANSFER CATALYSIS SECTION
4) COMMON ERRORS AND SUMMARY SECTION
WHAT I DIDN'T LIKE:
NO COMPLAINTS.
EXCELLENT CHAPTER!
Jones (Ch 20)
Good nomenclature section. Excellent NMR and IR graphics.
Very complete on acid-base properties of amines. More complete
than Brown & Foote re. solutions to overalkylation problem.
Interesting section on alkaloids. Good explanation of phase-transfer
catalyis.
Jones (Ch 6 and Ch 13)
The jones text presented the ideas clearly but was very dry
and lacking in creative displays of molecules, etc. At times the
text was also wordy. The common errors section in each chapter
was a good idea. The Jones is a fine text but I feel is the worst
I have looked at. The alert warnings in ch 13 should be used in
all texts.
Jones (Ch 6 and Ch 13)
A. The presentation of problems at the end of the chapters
were very impressive. Pages don't seem crowded, as so often occurs,
and lots of structures were used, instead of just formulas.
B. I missed the topical outlines that were presented in the beginning
of the chapters in B&F and the other books. Graphics were
seemed homogenized and uninspired.
Jones (Ch 6 and Ch 13)
(1) Layout of the text
There is no contents of the chapter sections at the beginning
of each chapter. The use of the color boxes for the nucleophile
and leaving group are not used consistently thoughout chapter
6. The use of red/pink background for the tables and the light
red color used to highlight the beginning of new sections is a
bit distracting. Key reactions are not listed at the end of the
chapters; however, a synthesis section is included within the
summary section. I like the summary division of New Concepts;
Reactions, Mechanisms, and Tools; Syntheses; and Common Errors.
This summary is a nice approach to wrapping up the chapter. All
that is missing is the actual key reactions.
(2) Clarity of the presentation
The text is presented in an easy-to-read format; however, it does
not appear to summarize the concepts very well. Chapter 6 lacks
any table presentations summarizing SN1 and SN2; E1 and E2; and
substitution vs. elimination.
(3) Logical organization of the material
The order of material throughout the book does not seem appropriate
in comparison to our current text.
However, the individual chapters are presented in a logical fashion.
(4) Overall usefulness as a text for this course
Overall, the best part of this text is the chapter summaries.
Otherwise, the aesthetics of the layout are displeasing.
Jones (Ch 6 and Ch 13)
Likes - I really thought that the common errors section at
the end of the summary would be very helpful to O-Chem students
I also felt like the book had a personal feel and like the text
worked through the problems with the students rather than just
presenting the material
Dislikes - I thought that some of the chapters should have been
in a different order, i.e. - Aromatics should have been later
Jones (Ch 6 and Ch 13)
Right off the bat, I felt that this book was easy and inviting
to read (based on the text). However, I didn't like the graphics.
I thought the mechanism were awful and this made it difficult
to follow. The text was really good but the graphics did not compliment
it as graphics need to. For me, Org. Chem is best understood by
looking at the graphics. Therefore, the clarity of these chapters
suffered. One thing I really like was how they handled stereochemistry
in these reactions. Other than that, the basic principles were
presented much better in B&F all the way through. I also really
like the summary at the back of the chapter compared to B&F
(B&F summaries at the end of the chapter are pretty bad-except
for their blue reaction pages). The aromatics chptr was especially
hard to follow. I felt really lost while I was reading it. The
logical flow of material didn't seem to work here. I was never
able to get into a groove while I was reading the chapters. I
felt the mechanisms were especially bad in the aromatics. They
really need a table or some different graphics to compliment there
surprisingly good text. For example, a table should have been
used to group the sulfonation, nitration, halogenation, &
friedel crafts. Even though B&F doesn't really use a table
for these reactions, I still felt that B&F present them better
than Jones.
Jones (Ch 6 and Ch 13)
The first thing that struck me about the Jones book is its
plentitude of graphics to accentuate the concepts in the text.
I was very pleased by this and found it helpful, being that the
text at times bacame very wordy. In comparision, the Brown &
Foote text would not elaborate on some concepts textwise, instead
being too brief in description. I also feel that the B&F did
not utilize visuals enough or as well as Jones, but the graphics
from B&F were superior to Jones. The Jones text did a very
good job of leading the reader through a conecpt, then building
upon that concept, using diagrams and pointers for review, whereas
the B&F would just give a reference section, ie. (sect. 3.8B)
and make the reader go back to correlate the concepts on their
own. Overall, I found that B&F and Jones both had points that
i liked and disliked over each other. I give Jones the advantage,
as I felt more comfortable with this text than the other.
Jones (Ch 6 and Ch 13)
Comments
I was very disappointed with the Jones' text. The following are
my comments for chapters 6 and 13 in the new text:
Both chapters were too long. The author was very wordy and failed
to get to the point. For example, Jones used 6.5 pages to describe
the inversion of stereochemistry in SN2 reactions. (Section 6.7b).
Jones' text did not have contents at the beginning of each chapter
or reaction summary at the end of the chapter. I found both features
very helpful in using Brown and Foote. (I was wrong. Jones does
have a syntheses page showing reactions, but it is not as easy
to read as Brown & Foote.)
Jones had too many diagrams that were distracting rather than
enhancing the text. For example, page 209 was unnecessary to show
the structure of alkyl halides. All I needed was R-X, and an explanation
of R and X. I didn't appreciate Jones' personal messages. His
comment that "organic chemistry is frustrating, if delightfully,
messy" (page 246) only made me feel less confident about
organic chemistry and his ability to convey it. Also, his references
to "we" and "my" seemed inappropriate for
a science text, Both texts did a poor job of synthesizing the
material on substitution and elimination reactions. Brown and
Foote made an effort at comparing and synthesizing material on
E1, E2, SN2, and SN1 reactions, whereas Jones lacked that effort.
Overall, I give Jones' text a poor rating of C. It lacks clarity
and professionalism.
Jones (Ch 6 and Ch 20)
LIKE: I like the summary sections with the "common errors"
and "synthesis" sections. The book is very specific
in explaining in an easy manner the substitution/eliminination
reactions and the amines chapter is very well put together as
well. The book is also very pretty and colorful :). DISLIKE: long
chapters, but I guess you can't have good, specific explanations
and short chapters at the same time.
Jones (Ch 6 and Ch 20)
I graded the layout fairly low on this book because I felt
confused about where I was and what I was looking at throughout
the chapter. While there were enough graphics in the chapters,
I felt like they were representing some things too much at the
expense of not highlighting another important topic. For example,
in Ch. 6, there was a plethora of diagrams on transition states
in Subst/Elim. reactions, but I had to hunt repeatedly to find
an overall summary of the general reaction mechanism. I appreciate
that Brown and Foote has consisently labeled boxes for mechanisms
that I can quickly refer to as a quick review strategy. I know
that Jones has them in the text, but they were harder to find.
I felt that Jones, in general, did not highlight important trends,
mechanisms, etc. and they could easily get lost in the text or
in the margin as one of the "figures." I imagine that
I would learn to navigate Jones' book just as I have Brown and
Foote, but these layout inconsistencies and deficiencies jumped
right out to me. It was unfortunate that I thought the layout
of this text was poor, because Jones' writings and explanations
in these difficult chapters were very fluid and easy to understand.
I liked that Jones "spoke" to us through his text...just
as I began to drift off, he would insert a sentence that was a
little bit less organic chemistry terminology-saturated and quickly
refocused me. I enjoyed his theoretical explanations behind the
behaviors in mechanisms, such as his explanations the interactions
between HOMOs and LUMOs in substitution reactions. On the flip
side, I sometimes felt that these explanations were a bit excessive
and at the expense of highlighting the more basic characteristics
and points of the chapter.
The organization of both of these chapters was very similar to
Brown and Foote, which I liked in our book. I still think that
Brown and Foote was more logical in teaching alkanes and alkenes,
along with stereochemistry, before substitution and elimination
mechanisms. It doesn't make sense to me to teach how to create
a double bond when you don't even really know what it is and what
its properties are. Likewise, Jones put the preparation of amines
section after the reaction of amines, which seems out of order.
I know that it was helpful for me in BF to have a quick review
(even just a couple pages) to review old reactions that yield
amines and introduce new reactions before we learned new reactions
with amines. Jones' in chapter questions were good and often entailed
applied thinking. However, I think that this text could afford
more solved in-chapter problems and more problems at the end of
the chapter.
Overall, I wasn't "wowed" by this book either. If you
could take the text from this book and the layout from another,
I would feel more comfortable recommending it. I just have found
the tables and reaction mechanism boxes in our book to be very
handy references.
Jones (Ch 6 and 20)
Dr. Wamser, this is the best book! I know I didn't turn in
all five reviews, but I did have a chance to look at all of the
books, and Jones was by far my favorite. It has a very
"laid-back" tone that is very easy to understand, and
sometimes the text is written in 1st person, making it seem like
you are actually interacting with the text rather than just reading
it. Also, unlike our current text, this one seems to have been
written by someone who actually remembers what it's like to see
some of this material for the first time. I have nothing bad to
say about it, but the following are some great things that I found:
Review of chapter 20:
The text actually gives tips, sort of like you do in class
(e.g. "The naming system used by the official chemical world
names amines analogously to alcohols." Pg. 1013)
The nomenclature section is much better.
More examples/less words: Organic chemistry is very complex for
me, and when I am trying to learn something complex I tend to
get confused when someone tries to explain it to me in words.
Brown and Foote tends to go into lengthy written explanations
about mechanisms and other things, whereas Jones gives
a brief written description and then more actual examples. The
examples are much more helpful than lengthy explanations.
4) There is a common errors section. This is also similar to what
you sometimes tell us in class. It is very helpful to have a section
like this so that I am alerted to potential foul-up spots that
tend to trouble students.
5) The reaction summary is excellent.
The "reactions, mechanisms, and tools section" is very
useful.
The homework problems seem much better in Jones. There
are more synthesis, reaction, and mechanism problems, and these
are the problems that I need the most work on.
Jones (Ch 13 and Ch 19)
Layout good structures and mechanisms
Presentaion very clear and easy to follow, but what i didn't like
about it was that the carboxylic derviative chapter was so long,
and boring, but i liked the armatic chapter it was so clear and
easy to follwo.
Organization was very organized and I like the aromatic chapter
Overall I think it will be a good book for the course
Jones (Ch 19 and Ch 20)
Comments
After reviewing four chapters from Jones, I am certain of my dislike
for this text. The following are my comments on two more chapters
(19&20):
* Jones' text does not have important definitions in a separate
column, a helpful feature found in Brown & Foote.
* The nomenclature in Jones is confusing. It contains too many
unnecessary examples (e.g. Figure 19.5).
* The mechanisms are difficult to find.
* In chapter 19 (carboxy derivatives), I would prefer to have
reactions presented based on what the derivative is reacting with
(e.g., water, alcohol, etc¡K) versus by type of carbonyl
derivative.
* The reaction summary at the end of each chapter in Browne &
Foote is very helpful. However, a similar syntheses page in Jones
is not as easy to read and follow. Also, it does not show the
section in the chapter that describes each reaction. Both texts
would benefit from adding the page number where the mechanism
can be found.
After reviewing Jones, I have a deeper appreciation for Brown
and Foote.
Jones (Ch 19 and Ch 20)
As I noticed in reviewing other chapters, the Jones text utilizes
visuals to a much greater extent, but the visuals in Brown &
Foote are of much higher quality. One particular segment that
stood out in these sections was a lack of spectroscopic visuals
to aide with the Jones text. I was disappointed by this. Again,
the Jones text is very complete for describing concepts in text
format, sometimes talking too much, but it follows up with several
examples such as in the Ch. on Amines. Sometimes the B&F text
feels like it just throws you right in and moves on. The Jones
book did have a glossary but no appendix. Again, a merger between
the two books is ideal, but i rate the Jones over B&F.
Jones (Ch 19 and Ch 20)
The layout of this chapter (19) was interesting. I felt that
it was way to jumbled at the beginning. Furthermore, the diagrams
presented way too much, too quickly. I felt that this organizational
format of presenting so much stuff all crammed at the start was
difficult to learn. It is key material, but the layout & organization
made it hard to incorporate. They took a similar approach as B&F
in their organzation of the reactions and not the derivatives.
I personally liked Carey's method much more. I felt that this
chapter in Jones was similar, but still more difficult than B&F
to learn. Derivatives chapter is all based on logical orgainzation
of the reactions and the derivatives themselves and I felt that
this book did a poorer job than both B&F and Carey. The clarity
was awful and I felt as though I didn't take away much knowledge
from the text. Furthermore, I felt that this chapter and the amines
chapter were hard to use. The amines was also packed full of stuff
at the beginning. IN a way, I found this to be intimidating. The
text was pretty straight-up like in B&F, which I liked. However,
the graphics did nothing to compliment the text, which, of course,
I hated. Pictorial representation is very important to me, and
this chapter lack it. Their logical flow was fine but I found
that the chapter...the whole book was hard to follow.
Jones (Ch 6) // Brown and Foote (Ch 8)
Jones-Use of the word underpinning? That guy has been waiting
his whole life to use that word!
Jones- Too conversational, he had me at first, then he lost me.
His trying to be my friend way too hard.
B&F-Much more concise, to the point.
Jones- Too busy when discussing Elimination reactions, too many
graphics.
Jones (Ch 6) // Brown and Foote (Ch 8)
Layout
Jones had graphics that were easier to use and were equipped with
comment bubbles that explained the details of each picture or
reaction. It was a little repetitious, but it really drilled in
the concepts for substitutiona and eliminations. Brown and Foote
had less graphics, no bubbles, but did have excellent pictures
along the lines of attractiveness (color, detail, computer images).
Clarity
Jones used a simpler language. It is easy to understand and is
unintimidating. However, sometimes I feel as though I am reading
a high school textbook--quote: "Understanding concepts and
applying them in new situations is the route to success"
(208). Thanks for the advice! Overall, in comparison to B&F,
it was easier to understand and I found myself reading passages
less times to understand them.
I love B&F's mechanisms. Jones is not so good at presenting
them Jones also lacks the awesome summaries at the ends of chapters
like B&F.
Organization
I like the way Jones flows into substitutions and eliminations,
first going over terms and explaining methods. They did a good
job of going over MOs for the types of rxns in the chapter. Both
of the books deal with the rxns in the order I see as the easiest
to understand: sn2, sn1, e2 and e1.
Both texts were alright at presenting the material, but Jones
had a simpler, repetitive approach that was easy to understand.
Jones (Ch 6) // Brown and Foote (Ch 8)
Chapter six provides a thorough overview of acid-base chemistry.
Section 6.7 to 6.9 provided a better and clearer textual explanation
of substitution. However, graphics are lacking in this chapter.
Simply not enough diagrams to help one follow the key points in
the material. Brown and Foote has a little less detail on substitution,
but the better graphics in the book helps fill the void. The HW
problems in B/F are a little easier, but there are more, thus
giving a better workout.
Jones (Ch 13) // Brown and Foote (Ch 20)
Jones has a good summary, but Brown's Friedel Crafts acylation
is easier to follow. We are not used to seeing benzene written
the way Jones does.
Jones (Ch 13) // Brown and Foote (Ch 20)
I can't help but emphasize the way Brown & Foote presented
the materials in this topic. The presentation was organized, easy
to follow and understand. It was a progressive presentation other
than an up and down the hill presentation. In essence, each material
presented was totallu discussed before moving to another.
The presentation in Jones was also progressive but less easily
accessible. The graphics were dull, rxns were within the text
and reduces the possibility for quick reference.
The presentation of mechanism in Brown & Foote the understanding
of rxns more possible and easier to follow than in Jones. I prefer
the way the materials were treated in Brwon & Foote than in
Jones
Jones (Ch 13) // Brown and Foote (Ch 20)
Layout: Jones focused too much on energy diagrams. B&F
had little graphics, except for mechanisms and rxns. I did love
the directing effects chart. B&F did a little bit better of
a job presenting what needed to be understood--this made for a
clean and organized presentation. Jones had too much.
Clarity B&F drills home ortho, meta, and para, which is good
for understanding directing effects. Jones mixes in much Nitration
stuff-this is too confusing. Nitrogen needs its own section!
Org. I didn't like how jones introduced diels-alder here. I gues
it's because dienes was previous in the book. B&F breaks the
chapter down in a good way. Jones goes through too many addition
reactions when the ch. title is "substitution reactions of
aromatic compounds"
B&F earns an A according to Wamser grading: it was clear and
left out extras whereas jones was a little wishy washy
Jones (Ch 13) // Brown and Foote (Ch 20)
Mechanisms in Jones book not detailed. Jones would rather
provide more text to explain details than to use an articulated
diagram. Both books provide decent explanation of aromatic substitution.
I think that the logical organization is better in B/F, in terms
of waiting to discuss aromatic sub. Mechanisms are explained better
in B/F. It is amazing how subtle details like using a colored
e- pushing arrow(B&F) as opposed to a black arrow (Jones)
adds to clearer understanding.
Jones (Ch 19) // Brown and Foote (Ch 17)
A. The presentation of spectroscopy was a huge improvement
over B&F - more concise and colorful. "Problem"
sections in the text were very nicely done less formulaic and
more theoretical/ text driven.
B. Graphics still seemed dull and the transitions between the
topics was not well executed.
Jones (Ch 19) // Brown and Foote (Ch 17)
Layout: Both texts did well covering so many rxns, but B&F
looked much better and didn't show lone pairs in the graphics,
which was easier on the eye Points
Clarity: This ch. was my favorite from B&F. It was very easy
to see the interchangibility of derivatives, where it was not
in jones. Jones was not that bad, it used a lot of rxns for repetitiveness
Organization: The types of derivatives were all layed out and
treated separately with the same formats for comparison, contrast,
and views of interchangibility. both were great
Both were good reads, and easy to understand
Jones (Ch 19) // Brown and Foote (Ch 17)
Jones-Nomenclature-Many examples: good!
Jones-The derivative by derivative layout is useful but messy.
Claisen in Jones is too busy, much better in B&F and has straight
forward graphics.
Reaction summary in Jones is better, compound by compound.
Jones (Ch 19) // Brown and Foote (Ch 17)
Jones' nomenclature is great, the visuals are good, and there
are lots of examples. I liked the summary of reactions on page
949. I noticed that there weren't any IR graphics like in Brown.
Even though we were only supposed to review Jones to page 967,
I did like the lightheartedness of the author on page 949 section
19.4 and the chapter summary.
Jones (Ch 19) // Brown and Foote (Ch 17)
Like I said earlier, it was initially very hard for me to
understand this material in Brown & Foote due to its presentation.
I had to re-organize the material in a way that could aid my understanding.
Jones did a better organizational job, in the sense that all about
each derivative was discussed one after the other without having
to go back and forth within derivatives like in Brown & Foote.
More helpful materials and rxns, were also discussed in Jones
than in Brown & Foote. Compared to Brown & Foote, I liked
the way the tables of mechanisms were presented and made distinct
from the body of the main text in Jones' text. It makes quick
search for mechanisms easier. This was not the case in Brown &
Foote. The rxns were treated but within the text making a quick
review of mechanism less possible especially for reference purposes.
In Jones' text, the table of synthesis at the end of each chapter
was also great. The use of captions was also relevant. The graphics
used in writing the sub-topics in Brown & Foote makes it easier
to see and access a particular material for quick reference than
in Jones'
Jones (Ch 19) // Brown and Foote (Ch 17)
Nomenclature coverage better in Jones, provides more examples.
Mechanisms on pages 956-57 provides good explanations in Jones
book.
Jones (Ch 20) // Brown and Foote (Ch 21)
Although I really liked this textbook, Brown has better example
problems in the text and I especially like Brown's connections
to real life situations. I reviewed Carey, Ege, and Jones to Brown
and Foote. I personally prefer Brown overall, but if you need
to change textbooks, I recommend Carey.
Jones (Ch 20) // Brown and Foote (Ch 21)
layout both had appropriate layouts with examples fo amine
compounds' spectroscopic properties. B&F used actual separation
diagrams, these are helpful for lab!
org. both gave physical props first. good for setting up uniqueness
of nitrogen compounds
clarity
Jones was a bit clearer and B&f didn't do as good a job with
azide ions, or breaking down primary, secondary, tertiary
Both were okay, but jones had a bit more clarity on a couple of
issues as outlined above
Jones (Ch 20) // Brown and Foote (Ch 21)
Commentary:
I was surprise to find that this chapter on Amines was much easier
to understand that Brown & Foote. Unlike the previous chapter,
mechanisms were all presented in the text. If a mechanism question
was asked, the answer was printed right below it. Perhaps these
chapters were not just written by one author...
Overall, I preferred Jones' organization. Brown & Foote would
be "flow" better if NMR, IR, Mass Spec was placed at
the end of the chapter. Further, Brown & Foote should introduce
the "Preparation of Amines" before the "Reaction
to Strong Acids" section. Generally, our text has given preparation
reaction before functional group reactions.
Things I like:
The mechanisms listed here showed complete reactions including
what reagent takes or donates protons. Brown & Foote simply
abbreviates this section. BUT, I'm now confused as to which mechanism
is correct. Brown & Foote describes the Nitrous Acid Reactions
with HONO -> N=O as the first step before it reacts with the
amine. Jones lists the reaction between the amine and HONO as
the first step before water is released giving diazonium ion.
Things I didn't like:
The nomenclature section was again presented in a better fashion
than Brown & Foote, yet it focused on common names than IUPAC.
Since we've been attempting to follow IUPAC standards, this section
"rubbed me the wrong way".
In the middle of the chapter, alkaloids extracted from plants
were introduced as a full section with nomenclature and simple
reactions. I think Brown & Foote does a better job introducing
biochemical examples either as background in a homework problem
listed separately in "Chemistry in Action".
As the text described the Hoffman Reaction, it introduced another
similar reaction, Curtis Rearrangement. This would have been a
great moment for comparisons, but since the Curtis Rearrangement
doesn't appear until two chapters later in the book, it seemed
premature to be introducing a comparison/contrast paragraph of
two sentences. However brief it was, this paragraph would still
leave students confused as to the point when they would not have
an understanding of what the Hoffman was being compared to.
Jones (Ch 20) // Brown and Foote (Ch 21)
The nomenclature coverage is better in the Jones book. There
is more explanations and examples. The coverage of the alkaloids
is increased in the Jones book. The reaction boxes are clearer
in the Jones book. But, the presentation in B+F is more clear,
thus extensive summary is not required.
Jones (Ch 6 and 13) // Brown and Foote (Ch 8 and 17)
Like : This book helps me aware of the common errors of other
organic chemistry students usually made. There is also a summary
of what I would expect to learn through the chapters, and there're
a lot of symbols that help to memory the new material easily.
Don't like: The chapter is too long, and there are too much things
covered in each chapter. There're about 10-20 pages longer than
the Brown's Textbook.
Jones (Ch 13 and 19) // Brown and Foote (Ch 20 and 17)
Things that I liked:
This book seemed to be close in userfulness to the current text
offered. I liked the organized approach to the material and the
graphic method of explanation of mechanisms.
Things that I didn't like:
I liked everything almost in equal weight as the current text.
This text was my favorite of those reviewed for this assignment.
Though I didn't feel an extraordinary advantage of this text over
the current B&F.
Jones (Ch 13 and 19) // Brown and Foote (Ch 20 and 17)
Layout: JOnes has Very good graphs and pictures especially
in chap 13 Energy VS Rxn progress diagram. From chapt 19, I liked
the way they presented the nomenclature showing how the names
are changed when different substituents are attached to the molecule.
Clariety: Jones is terrible at showing what's important in the
mechanism. For example in chapt 19, Add'n and Elimination rxn's
of esters, it does not clearly tell you that one rxn is base induced
and the other is acid-catalysed. IN Brown & Foot you would
have important mechanisms presented in a box with brief description
of important steps. Further in chapt.13, p.582-583, it bothered
me a lot that only at the end of the page ( bottom of page 582
) the author reveals that addn' reactions with benzenes don't
occur at all! Someone reading the material for the first time
could easily oversee it!!
Organization: Jones gives you too much information, it would be
difficult for someone going through the material for the first
time to learn what's really relevant. Chapt 13, sections about
Diels-Alder rxn, and 13.3, called "other rxns" - I really
don't think they were important. Besides, the summaries are not
as well presented as in BRown & FOot. IN Brown & Foot
all important rxn are briefly and clearly organized at the end
pf chapter (blue pages )
Overall: JONES is a good reference book because it has good pictures
and graphs but I would not like to have it as textbook.