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Seyhan N. Ege

Organic Chemistry: Structure and Reactivity, 4th Edition, Houghton Mifflin, 1999

Ch 7 - Substitution/Elimination
Ch 14/15 - Aromatic Substitution
Ch 20 - Carboxylic Acid Derivatives
Ch 22 - Amines

Ege
Things I liked about Ege:
1. Give more explanation of definitions it provides.
2. Gives more examples with different substituents for mechanisms.
3. More information given on each example (i.e. boiling points, relative size, etc)
4. Good diagrams of reactions, very thorough.
5. Summary of reactions at the end of chapters in tabular form, therefore easier to get basics for flashcards.
6. Breaks down carboxylic acid reactions a little more, and is good for students who learn by example (like myself)
7. I liked that there were a lot of examples sprinkled between the text, it helped to immediately have examples to focus on as I read, instead of as in B & F, where I had to try to visualize what they were explaining as I went.
Things I did not like about Ege:
1. It had almost too much information packed into each page, and was kind of overwhelming at times.
2. Text summary at the end of chapters was too short. I sometimes read these before I read the chapter to get an overview.
3. Important topics a little difficult to pick out and focus on in body of text. They didn't use color to point out the key parts of reactions as in B & F, even though they gave more examples.

Ege
1. chapters were really easy to understand and follow.
2. The carboxylic derviative chapter was really easy to understan, and made
more sense, cause it was divided to 2 chapters which I really liked.
3. Got good homework problems.
1. I kind of liked that book didn't disslike much about it

Ege
LIKES: There are none.
DISLIKES: Boring! Too small of print, no pictures or helpful graphics, no "real world" application problems or stories. (Those are interesting and helpful). I
opened up this book and immediately started feeling sleepy!! NO KIDDING! DO NOT GET THIS BOOK! It will torture students for years to come.

Ege
Like: This text have "Look ahead" section that I like the most because once again I know and be prepared of what I would learn through reading the chapter. There are visualizing the reaction, that helps me visualize the reactions in my mind of how the products or reactants look like. Don't like: In the problems solving, it is hard to recognize which section this problem belongs to.

Ege
This text, along with Jones was one of my favorites. Ege was similar to Jones in the layout and organization of the material. It had the right combination of both text and reactions, and the mechanisms were clear. In this text, I read chapters 14 and 15, Carboxyl Derivatives and chapter 22, Amines. Features I like are the descriptions of the physical properties of the compounds. I also like the Ege split Carboxylic Acid Derivatives into two chapters. One was "Carboxylic Acids and their Derivatives I, Acyl-Transfer Reactions," and chapter 15 was "Synthetic Transformations and Compounds of Biological Interest." Ege uses many biological compounds, such as acetylcholine to introduce new reactions, and this helps relate organic chemistry to other fields and to the real world. Ege is also good at linking and comparing new reactions to ones that have already been covered. This is a good learning technique, in that students familiar with one kind of reaction can distinguish similarities in a new one, never seen before. I also liked the "Problem Solving Skills" section in the chapters. In the "solution" part of these sections, Ege gives a step by step method of how to solve similar problems.

Ege
Did not show too many mechanisms, but when they did, they were fairly helpful. Great job showing all resonance forms. Not too many graphics which I think helps students. Lecture will definite have to be a big part to allow students to get a 3-D feel for things

Ege
Good use of tables, but tended to explain afterwards. I find it better to show then explain instead of giving all instances, and then explain. The text was a bit dry and impersonal, and tended to drone on. This may lose readers. This text was not as user-friendly as the other books

Ege (Ch 7)
WHAT I LIKED:
1) THE REACTION MECHANISMS VERY CLEAR
2) POTENTIAL ENERGY DIAGRAMS
3) MOLECULAR MODELS USED WERE VERY CLEAR IN DESCRIBING THE SIZE OF
AN ANION AND IT'S INTERACTION WITH PROTIC SOLVENTS SUCH AS WATER.
WHAT I DIDN'T LIKE:
1) SUMMARY WAS TOO SHORT
2) NO FINAL TABLE OF REACTIONS TO TIE UP CHAPTER.

Ege (Ch 7)
This book had was pretty good I felt. There were a few really good problems on how to think through problems on subst./elim., and what sort of thought processes you should being using. This is important here and was very helpful. There are other problems given also, but these had no help with solving them, which was not as good. Some of the electrom pushing mechanisms seemed a bit jumbled and hard to follow. The steps are not numbered so that added to difficulty. The book was not much to look at, but it explains things very well. If the visual problems are overcome this is a good text for a class.

Ege (Ch 7)
Likes:
The problem solving skills sections is helpful. It walks you through the concepts of the chapter by using questions and answers.
A lot of "visualizing the reaction" sections that shows the how the reaction takes place (similar to the "mechanism" section of Brown & Foote).
Topic was neatly section off to small groups.
Good informative section on nucleophiles.
Dislikes:
Too many "Problems 7.X", there were a total of 24 in chapter 7. It interrupts the flow of the reading.
No captions in the "visualizing the reaction", only the pictures. It would be helpful to have some captions explaining what is happening.
Attempts to give too much information. Section on biological leaving group was interesting, but distracting when trying to learn the basic concepts.

Ege (Ch 14/15)
I really liked this text a lot. The length was proper in that there was a good division of the ideas. The mechanisms were both very clearly explained, and were placed in boxes, which made them stand out. Table 14.1 "Summary of Reactions Used to Prepare Acids" and Table 15.1 "More Reactions of Acids and Acid Derivatives" were excellent because they provided the starting materials, reagents, intermediates, reagents in second stage, and the products. The discussion of 15.4 regarding lipids, fats, oils, and waxes, was both interesting (caused me to make a "real world" connection) and very clear. The only part of this chapter, which I didn't like, was

Ege (Ch 14/15)
There were only a couple of things in the Ege book that struck me as being bad:
The nomenclature section should come first. I noticed that the "properties" section came before nomenclature. It just seems that since the nomenclature is usually the most straightforward and easiest section of a chapter that it should precede the other sections. It also makes me feel better to start out with something that I know I can do and then to progress to the more difficult material.
The different sections of the chapter are not as clearly divided as they are in Brown and Foote . I know this may seem trivial and unimportant, but for me it is helpful if different sections (e.g. problems, mechanisms, actual text, etc. ) are clearly separated, using color or actually enclosing the material, diagram, or problem inside a box or perhaps just inserting lines, separating the material from the rest of the page.
The problems in the back of the chapters do not seem like they would be very helpful in preparing me for a test. A large part of your tests consists of mechanisms and syntheses. It would be helpful to have more of these kinds of problems in the homework section. The Brown and Foote book doesn't offer a very good homework section either, in my opinion. I really liked the homework section in the Jones book.
Following are some things that I liked about the Ege book:
The "visualizing the reaction" sections are extremely useful! I say this because it helps me "follow" the electrons and the atoms. Sometimes it is difficult for me to follow if I am expected to deduce what is happening. I actually need to see where things are going.
Tables are always useful. (ex: table 14.1 on page 579- "summary of reactions used to prepare acids").
The interconversion table is a great idea! There is an example on page 580. We have this kind of table in our solutions manual, but it would be nice to have it in the actual text for quick reference. Also, sometimes due to "steric hindrance" I can't fit my solutions guide in my bookbag.
The "One Small Step" web sections sound interesting. Obviously I haven't tried one because I don't have the book at my computer, but I can say that sometimes it helps to have something different to do. It helps to break the monotony that studying can sometimes impart.
5) Reaction Summaries : I think that every Organic text should include a reaction summary. Chapter 15 has a better reaction summary section than chapter 14. I did skim through the rest of the text, and it would be nice if the summary sections were a little more consistent in helpfulness.

After reading these chapters and comparing them to chapter 17 in Brown and Foote, my conclusion is that the two are of comparable usefulness in learning the material. If I could take the "visualizing the reaction" sections and stick them into the Brown and Foote text, which has the better reaction summaries, then that would be great! I see no evidence that Ege is a better textbook than our current text. The following are my grades for the chapters:

Ege (Ch 14/15)
Commentary:
In general, after reading Ege isn't necessarily the easiest verbiage to read, but it certainly runs smoothly. Often, there are transition statements/questions that gently guide the reader to the next topic. Brown & Foote is employs only subheading within each section to introduce another topic.
Things I like:
Table 14.2 synthesis graph is very helpful.
The text describing the mechanism is much more lucid than in Brown & Foote.
Synthesis questions are GREAT!!! It provides a step by step plan toward approaching synthesis questions. This gives students a different focus when learning mechanisms. Instead of memorizing them as "vocabulary", they would be memorizing them within the context of other reactions.
Things I don't like:
This chapter includes biological molecules. There are later chapters that are devoted to biomolecules so I feel it is unnecessary to start introducing complicated molecules in the first half of the textbook.
I prefer Brown & Foote's treatment of carboxylic acid reactions in one chapter then the derivatives in another. Ege intersperses carboxylic acid reactions with derivatives.
The presentation of graphics and the type setting is not easy on the eye. Brown & Foot had more white spaces on each page, hence its not as intimating. The text, problems and figures are crowded with little graphic distinction to delineate sub headings and sections and problems. Visually, reading this book for too long would strain my eyes.

Ege (Ch 20)
Likes:
A better job at explaining directing effects. The structures are well displayed with all their resonance forms. The NO2 group is shown as a resonance with charges vice just NO2.
Uses a lot more illustrations in its discussion.
A lot of "visualizing the reaction" boxes.
The summary table of the reactions are separated into different tables, one for electrophilic and one for nucleophilic.
Dislikes:
Again, too many "Problem 20.X", interrupting the flow of the reading.
No captions in its "visualizing the reaction" boxes.
The summary table lacks captions and references making it hard to go back to the text to review a certain reaction.

Ege (Ch 20)
I really liked the order of the ideas presented (ortho/para and meta discussions first, then the mechanisms were discussed). The explanations were clear, the colors were soft, and the tables and mechanisms were clear and well displayed. The only problem with this book was that it had no sample problems, and its ortho/para vs. meta, and activating vs. deactivating table was not as good as Brown and Foote's. Overall, I really liked this book a lot. It was the only one that discussed aromatic substitution near the end of the book, after its discussion of mass spec, NMR, and IR and UV. I think that learning about mass spec, NMR, IR and UV first, and then about the substituents, gives us a better understanding of the substituents. Therefore, students can understand why they react the way they do and why they have certain special properties. It does not make sense to place NMR at the end of a textbook when all the while you can be learning about it.

Ege (Ch 20)
Commentary:
In general, after reading Ege isn't necessarily the easiest verbiage to read, but it certainly runs smoothly. Often, there are transition statements/questions that gently guide the reader to the next topic. Brown & Foote is employs only subheading within each section to introduce another topic.
Things I like:
Ege placed the Nitrogen and Sulfur Reactions after the Friedel-Crafts. It flowed better than in Brown & Foote which also seems to place nitrogen and sulfur reactions in the oddest places. It almost appears that Brown & Foote would just slap on a remotely similar nitrogen/sulfur reaction adjacent to the carbon counterparts. If they had to intersperse amino thiol reactions, they should have decided to put it at the end.
I also liked the occasional rhetorical question in Ege's chapter, which served as a transition from once topic to another.
Synthesis questions are GREAT!!! It provides a step by step plan toward approaching synthesis questions. This gives students a different focus when learning mechanisms. Instead of memorizing them as "vocabulary", they would be memorizing them within the context of other reactions. I prefer to have a synthesis discussion within the text instead of just as a homework section at the end of the chapter as in Brown & Foote.
I also like the fact that the answers are always located on the next page so you have the chance to work it out without being too tempted to look at the answers right away.
Things I didn't like:
The presentation of graphics and the type setting is not easy on the eye. Brown & Foot had more white spaces on each page, hence its not as intimating. The text, problems and figures are crowded with little graphic distinction to delineate sub headings and sections and problems. Visually, reading this book for too long would strain my eyes.

Ege (Ch 20)
Reasons and comments:
Table 20.1 in Ege was not as good as B&F's Table 20.1;
Ortho/para and activation/deactivation between Halogens and Nitration reactions should have been introduced after the having gone over all of the reactions first; substituent effects should have come later, like in B&F;
Its information is too spread out and could have been more condensed like in B&F;
Halogenation and Nitration are together, but there mechanisms are not introduced until later; B&F has its organization more logical;
Problems, but no solutions throughout the text; I thought that theses were helpful in B&F because it enabled you to test knowledge before going on with reading;
I liked Ege's Sulfonation reaction, which B&F didn't go over in depth;
Ege has many drawings on the delocalization of the positive charges, shown like in lecture and why certain structures are favored or not;
Meisenheimer complex was explained more clearly compared to B&F;
Fiedel-Craft reactions should have been presented with the Halogenations because it's somewhat similar (same catalyst);
Overall, I think that Ege has its information too much spread apart in a non-logical manner, it could have been condensed more like B&F. I really liked B&F's Ch 20 because it presents its info really well, therefore, I would have preferred this book over Ege's.

Ege (Ch 22)
WHAT I LIKED:
1) SUMMARY AT END (OF REACTIONS)
2) THE CONNECTION BETWEEN BIO AND CHEM
3) MECHANISMS VERY CLEAR 4)SECTION ON DYES AND BASE INDICATORS VERY
INTERESTING
WHAT I DIDN'T LIKE:
1) EGE NEEDED TO BE A LITTLE CLEARER ON SECTION 22.5 REACTION WITH NITROUS ACID. I WOULD HAVE LIKED TO SEE: RXN WITH TERTIARY, RXN WITH SECONDARY...ETC.
OVERALL I RECOMMEND EITHER B&F OR JONES. I AM BIASED WHEN IT COMES TO B&F, FOR IT IS THE TEXTBOOK FROM WHICH I HAVE LEARNED A GREAT DEAL OF INFORMATION. I FOUND B&F TO BE EXTREMELY WELL-WRITTEN, INTERESTING, AND FOR THE MOST PART WITHOUT ERROR. KEEPING THIS TEXTBOOK FOR NEXT YEAR WOULD BE A HELP TO FUTURE ORGANIC CHEMISTRY STUDENTS. THANKS-

Ege (Ch 22)
Obviously I felt this chapter was a step down from the other I reviewed. The chapter seemed to get somewhat complex quickly, which was not helpful. Also, again the book is very dry and bland to look at. Maybe some won't mind, but I just didn't like that at all; huge lack of color. Many of the reactions they show use large molecules, which is interesting, but when just learning basics it would be easier to use smaller ones. There are lots of biological references, so that may be a strong point in the eyes of many. The problme solving sections were also again very good, but there should be more of them. The summary was not very well done here either, it seemed a bit overwhelming. Not as good as the previous chapter and though still well written, it would be hard to study and read from.
Overall the best textbook I have reviewed has been Carey.

Ege (Ch 22)
Commentary:
In general, after reading Ege isn't necessarily the easiest verbiage to read, but it certainly runs smoothly. Often, there are transition statements/questions that gently guide the reader to the next topic. Brown & Foote is employs only subheading within each section to introduce another topic.
Things I like:
The best attribute to Ege is the "Problem Solving Skills" section. This section seems to occur in every chapter. It provides a step by step plan toward approaching synthesis questions. This gives students a different focus when learning mechanisms. Instead of memorizing them as "vocabulary", they would be memorizing them within the context of other reactions. I prefer to have a synthesis discussion within the text instead of just as a homework section at the end of the chapter as in Brown & Foote.
Things I didn't like:
Biologically Active Quaternary Nitro Compound section was placed within the main text of the chapter. There are later chapters that are devoted to biomolecules so I feel it is unnecessary to start introducing complicated molecules within this chapter. If need be, Ege should have separated this information as Brown & Foote does with their "Chemistry in Action" section.
As with the other chapters, not many mechanisms were elucidated on the text.

Ege (Ch 7 and Ch 20)
Likes - Table summaries at the end of the chapters; the manner in which it taught students what questions to go through in their mind when they see certain types of problems Dislikes - The green reaction boxes drove me nuts! That color! Ege (Ch 7 and Ch 20)
Things I like:
I appreciated some things about this text which seem subtle, yet seem to impact me when I'm spending a great deal of time with a text. The early introduction of all the varied types of reactions which will be encountered throughout the course (ch. 4) which was referred to in chapter 7 seemed logical to me. I like the way the graphics are done in a clean, simple manner using pleasing and consistent colors throughout. Each example was clearly labeled with the IUPAC name in each reaction sequence. In chapter 7 the use of a table to show the different nucleophiles used for various types of synthesis was very helpful. The problems scattered about the chapter were well placed. Each group of problems approached the topic in several ways. I was especially pleased with the "problem solving" sections which helped develop a method for working through the type of reactions being discussed. In chapter 20, I really liked the graphical and textual coverage of molecular orbits. The discussion and graphical aids for delocalization of charges and resonance was in a similar manner to your style of drawing in lecture which provided continuity. Finally I was very impressed with the summary of reactions at the end of the chapters. They had a 'flash-card' quality to them which is helpful when one doesn't need detail and commentary while trying to commit reactions to memory.
Things I don't like.
One thing I didn't care for in this text were the side bars "One Small Step". Like most of the sidebars in these texts they really get in the way and are visually distracting while trying to focus on the main material. The only other problem is the slight dryness of the text, which may or may not be so bad when attempting to resolve reactions and mechanisms ("just the facts, ma'am" approach).

Ege (Ch 7 and Ch 20)
Comments
Ege's text had nice boxes titled "visualizing the reactions."
The new text contained appropriate graphics. They were not overdone and didn't take up a lot of space like in Jones.
The text was very technical, which I appreciated.
I liked the organization of the text. It was easy to follow and topics were arranged in a logical order (see chapter 7).
Some topics were covered too briefly (e.g. solvent effects). It would require a in-depth lecture to supplement those topics for better understanding.
Sections titled "problem solving skills" would be good concept questions. The problem is broken up so that it isn't overwhelming.

Ege (Ch 7 and Ch 20)
Chapter 7 gives an example of Ege's excellent use of space in his layout of the material. Abundant space is given for the text as well as the graphics, giving clear visualization. Words are easily readable (font is good and clear). I really like the problem-solving skills section giving questions a student should ask him/herself when working through problems and reactions ("think like a molecule" type of material). In presentations of mechanisms, rather than using step-by-step mechanisms like Brown&Foote, Ege uses the method which a student would use on an exam, not a step-by-step method.
Chapter 20 has a good flow and order of subjects. The chapter begins with all nomenclature and moves on to reactions, explanations of stabilities of resonance, and reactions. Tables are well organized showing electrophiles, reagents, and their reactions they're involved in. Ege does take too much space in displaying NMR graphs. Thorough explanations about how and why conditions for reactions are appropriate add to the details of each reaction. Clear and understandable language is used in descriptions and ideas are joined smoothly. Presentation of "fundamental" concepts/terms are very clear and do not leave anything out. Ege clearly explains things using language between layman and professional terms. In Brown&Foote, I liked how they gave example questions throughout the chapter whereas Ege only gives couple questions one must answer without some kind of guidline in how he wants the student to answer the questions. Like Brown&Foote, it's great how Ege includes real-life biological examples in which the presented ideas or reactions are involved. I like how Brown&Foote included a reaction section summarizing all the reactions of the chapter. But Ege summarizes the starting reagents, intermediates, reaction reagents and products. Organization is logical and easy to follow.

Ege (Ch 7 and Ch 20)
A. The graphics were very similar to B&F - both had good quality and user-friendly graphics. The "visualizing the reaction" sections were a nice touch.
B. This text seems to be missing key components. Definition of terms were only given in text - not very conducive to a quick review of the material.
There is no topical summary at the beginning of the chapters for quick reference. The chapter summaries are too brief and often miss key points.
The problems given in the actual text are too lengthy - breaking the flow of the information given. I think that lengthy problems should be saved for the end of the chapter. I see this text as being cumbersome and not the best choice.

Ege (Ch 7 and Ch 20)
This textbook had very, very dense passages. Breaking up the text with bolding, italicizing or color would help us maintain our attention and our ability to pull out the important points of the text. As it is, it was easy to miss important information because the discussion seemed to go on and on. But the chapters did provide good problem-solving sections which prompted you to ask the right questions about how to solve a problem.
Subst./Elim.:
Organization of this chapter was not as effective because it jumped right into comparing SN1/SN2 without fully developing the mechanisms individually first. It seems that this type of layout could contribute to getting the two topics mixed up.
There was no comparison section of SN1/E1, SN2/E2. Only in the chapter summary was it available.
Arom. Subst.:
Again, difficult to pull out important points of text, because of text style monotony.
Limitations to Friedel-Crafts alkylation not completely discussed (no mention of electron withdrawing groups hindering reaction).

Ege (Ch 7 and Ch 20)
LIKE: I like the diagrams they have for visualizing the reactions better then the key reactions in Brown and Foote. They also have really nice step by step solutions to example problems after each section which show you the thought process involved in coming up with the right answer to a problem. DISLIKE: The reading seems to be "dryer" then in Brown and Foote.

Ege (Ch 7 and Ch 20)
(1) Layout of the text
The chapter content is not listed at the beginning of the chapter to show topics by section. Some pages have too much text, whereas other pages are filled with diagrams. This format does not appeal to me. The diagrams do not relay in words (in either a figure label description or bullet points within the diagram) what is occurring in, for example, a mechanism. The tables are not formatted for easy reading and reviewing the key points. There seems to be little use of margin space. Key reactions are not listed at the back of chapter 7. The homework problems are not laid out in a manner in which to distinguish the beginning of any given problem.
(2) Clarity of the presentatio
Chapter 7 does not have a summary presentation of the effects on the rate of reaction. Summary of SN1, SN2,
E1, and E2 reactions are not in table presentation to help tie everything together.
The discussion of the effects of substituents on further substitution is not clearly introduced in chapter 20. This topic should have its own subsection. The reactions at the end of chapter 20 included incomplete reaction info for electrophilic substitution, but not nucleophilic substitution.
(3) Logical organization of the material
The chapters, as well as the text, were presented in a logical, easy to follow manner.
(4) Overall usefulness as a text for this course
In comparison to our current text, I would not recommend changing to this text.

Ege (Ch 7 and Ch 22)
Layout: The layout of this text was very consistent, but rather dull, I must say. I really liked the visualizing the reaction pieces of each chapter because it provided a variation on pieces of information that are normally presented in text. However, these were still not barebones representations of the general mechanism, which we were left to hunt for until the end of chapter summary. Generally, I thought the graphics side of this text was lacking. There were no pictures and very few tables, both of which offer good alternatives of depicting the same information in varied ways. OCHEM is such a heavy topic that it is nice to have a break in the monotony of reading difficult section after difficult section. I found the reaction summaries at the end of the chapter a little less convenient (maybe just different from our way of doing things), although it does present a useful tool for quizzing yourself backwards and forwards. Clarity: The text read very well, although not as clearly as the Jones text, for example. The clarity of the presentation would have been enhanced with concise tables that extracted some of the information on trends in nucleophilicity, reactivity trends, solvent effects, Subst. vs. Elim. Comparison (Ch.7) and basicity trends, etc. in Ch. 22. In fact, he did not even emphasize trends in basicity or pKbs at all, both of which were difficult concepts for me to make sense of in our text. With such a short description, I would have been lost without my prior understanding. I liked how Ege wove a periodic review into his text, by mentioning a word and taking the time right then to review what it actually meant and how it related to the subject under current discussion.
Organization: The organization made very good sense, providing just enough review before introducing new information. Again, however, alkenes were not taught before teaching E1/E2. Ege's sections on problem-solving skills (7.2) provided excellent organization for answering problems in the text, and would help a student develop a consistent strategy for answering Subst./Elim. Problems, as well as many other problems in OCHEM. As much as we'd like to think we can devise our own foolproof strategies, we ARE students and are learning this for the first time, so this extra well-defined guidance is very appreciated.
Overall: It would be much easier if we could fuse all of these texts in to one. I like Ege's strategies of presenting heavy loads of information in this text, but thought this book was too heavy on words. If this book were to be chosen (which wouldn't be a terrible choice), it would be important for the visual learners to use Chem TV and to create their own graphical summaries of integrated information (which is an excellent learning tool). Still, of all the five books, I like this and Carey's text the best.

Ege (Ch 14/15 and Ch 20)
This text book DID NOT state things simply. For naming, instead of drop the final 'e' and add 'x' as in B&F, it was....replace the e with the name of the hydrocarbon having the same # of C atoms...not simply stated. This chapter (14) did however have very nice sections where they presented problem and then asked questions necessary to answer the problem. B&F does not do this often. They walked you through how you need to be thinking. There was a new reaction: Schotten-Baumann and plenty of questions. The end of chapter summaries do not give specific examples, it gives: R-COOR + RMgX going to CRRROH (with prime notations) but that didn't help a whole lot for anything specific.
I also thought that chapter 20 described how to identify o, m and p directors a little too late. We'd already put them on the ring and it was a 'by the way this is why you did that' section. I liked how they had descriptions under the individual mechanisms saying why they were doing what they were doing. They also had a nice way of showing resonance on benzene (little pink circles on the C bearing the charge).

Ege (Ch 14/15 and Ch 22)
Things I like The labeling of derivatives and reagents in all the examples and reaction mechanisms is well done. The nomenclature portion of the chapter is very straight forward and helpful in trying to sort that out. As in my last review of Ege, I appreciate the simple layout and organization of the reaction mechanism graphics, they are easy to keep straight and mentally group. The "problem solving skills" sections seem well placed to prepare you for doing the assigned problems. Once again my favorite portion is the simple "flash-card" style reaction summary section especially the two-way table in the carboxylic acid derivatives chapter.

Ege (Ch 14/15 and Ch 22)
Chapter 14, discussing carboxylic acids and their derivatives, has a good use of examples and including them in the text. Brown&Foote gives examples and never uses them again. Ege gives pertinent information and none is irrelevant. Visualization of mechanisms is good and the layout is excellent, clean, and clear. Many sections, once again, have the problem-solving skill sections which is great. These one-page sections show Ege's methods in "how to think about a problem." Summary Tables are wonderful, easy to read and follow; spacing is appealing. Logic in the chapter's organization is smooth in its flow, from introducing the different derivatives to reactions and a real-world application section.
Chapter 15, like previous chapters, shows how a student would write a mechanism on an exam, not step-by-step (although Brown&Foote are good in explaining the step-by-step method). This presentation gives a natural flow of mechanisms rather than steps one must memorize and know. There is a perfect balance in use of colors, not too bright, not too dull. The graphics give attractiveness to the page as well as the information presented. Ege gives a good thorough coverage of materials and details without over-discussing or omitting pertinent information from what is presented. Nothing is difficult about the organization; Ege's textbook is definitely "student-friendly."
By Chapter 22, Ege has good logical succession throughout the book from chapter to chapter. Subjects flow smoothly and relate to each other, not jumping around (e.g. placing the chapter on amino acids right after the amine sections and not waiting a couple chapters until mention). Instead of learning information that we need to know only in lecture and in a professor's notes, Ege's textbook helps in contributing to a student's broader knowledge because the information is written in the text and would not sound like anything that the student should disregard.

Ege (Ch 14/15 and Ch 22)
The Ege book appears to be the standard style textbook for O-chem. It has a similar but effective use of highlighting and boxing for mechanisms. The Mechanism boxes are somewhat less effective in displaying the Rxn. They do not have numbered steps so the reactants-->products can appear jumbled. The breakdown of sub-sections seems appropriate and consistent with the B&F text. Overall, I like the Wade book, but i see little benefit in changing from the current text to this one. Little is gained from it.

Ege (Ch 14/15 and Ch 22)
Chapter 14&15 were good chapters. Right away, I loved the fact that they separted derivatives into two chapters. Since, in my opinion, it covers the most amount of info, two separate chapters breaks up the concepts. Furthermore, the way that they grouped the two chapters was very good. I really like the organization in that they showed all of the derivative at the start (however, it wasn't over-bearing). This eased me into what we will be covering in the chapter. The text was very descriptive and the diagrams complemented the text nicely. Example is 14.1 was very helpful to understand the relative stabilities of the derivatives at hand. The chapter flowed fluently and I really liked the way that they organized the material. Everything they did was clear and helped me to master the knowledge that they were presenting. I felt as though the book really taught the info to me. Also, the choice to have two chapters instead of having twice as many sections was nice. The amines chapter opened with the same idea as the derivatives chapter and this was good. The organization of the material was logical and presented in a manner that I felt it was easy to follow. I noticed that this amines chapter has many more reactions than our B&F does in their amine chapter. I really like the way they laid out the "visualizing the reaction" boxes. The mechanisms in this book were the best of all of the textbooks. The only complaint is that they should have incorporated the tables throughout the chapters instead of, or in addition to, having the big table in the back. I really got into the text and found that the clarity of it was great and easy to follow. I especially like the "synthesis of amines" part better than in B&F.

Ege (Ch 7, 14/15, 20, and 22)
Layout was very clear and got a lot got structures and graphs A was very easy to follow, and understand
Presentation very organized and all the chapters made reallly good sense, and was very clear and short, which i really liked. and it was so easy to follow and got really good examples
Organization was very organized and materials were very clear to understand. the carboxylic chapter was really easy and they divided it to 2 chpaters and it was really easy to understand
Overall I think it will be the best book for the course

Ege (Ch 7) // Brown and Foote (Ch 8)
Positive remarks for Ege: The layout of the text made it easy on the eye in terms of transitioning from one section to another, colored box reactions, and their problem solving skills (using a step by step procedure)were excellent and very helpful. Negative remarks: Answers to the sample questions would have been better and biological info should have been placed elsewhere. Positive remarks for B&F: the additional information on "Chemistry in Action" has always been a favorite of mine, with good layout of the text in terms of charts for protic and aprotic solvents, etc... Negative remarks: when reading this chapter, I remembered at times, some of the information was not that clear and a bit vague. I remember having to rely on another text.

Ege (Ch 7) // Brown and Foote Ch 8)
The graphics used in Ege are larger and easier to follow than in B&F.Ege shows more mechanisms using different nucleophiles,B&F on the other hand shows only one example. The mechanisms in B&F are better organized and each step is labeled. Ege does not have a summary of reactions at the end of the chapter.
Overall I think B&F is the better book for this chapter.

Ege (Ch 7) // Brown and Foote Ch 8)
a) Things I liked:
Good graphic to illustrate protic solvent e.g. fig 7.6
I liked the background coloring for the "visualizing the reaction" which sets it apart from the text.
b) Things I didn't like:
Ege did not include a summary list of key reactions at the end of the Ch.
Problems in the middle of the text were not preceded by worked out examples.
B&F location of fig 8.7 for E1 was in the E2 text section -> confusion.
Ege fig 7.1 shows a "bimolecular substitution" that uses Br as both the incoming and the outgoing molecule. B&F on pg277 does a better job of showing SN2 reactions as involving two different species.
_ B&F could have done a better job of describing solvation.

Ege (Ch 7) // Brown and Foote (Ch 8)
Brown and Foote is a far superior text in my opinion. Ege has a poor summary, some of the print is too small ( example is on page 256) , there are not enough tables to organize the most important points. The section "visualizing the reaction" is good, however.

Ege (Ch 7) // Brown and Foote (Ch 8)
Liked: The Problem Solving Skills sections in Ege were helpful, as well as the section for visualizing the reaction.
Didn't like: Ege doesn't summarize the Key Rxns like Brown and Foote.

Ege (Ch 7) // Brown and Foote Ch 8)
Comments: Ege had the problem solving skill questions that walk one through the analysis of substitution and elimination products seem useful for introduction to the concept, leading the student and showing how to analyze, step by step.
B&F 's graphics are much better for comparing nucleophiles, nucleophilicities, etc. More refined as well.
Ege jumps all over when introducing new concepts and refers to later chapters; ie. stability of alkenes.
Ege is useful to see the visualizing the reaction boxes right when a reaction is discussed, but they are kind of thrown out all at once.
Energy diagrams in B&F are easier to read & understand.
Biological leaving groups-too much, too fast.

Ege (Ch 7) // Brown and Foote (Ch 8)
Reasons and comments:
"Visualizing the reaction" green boxes were somewhat helpful because it showed the substitution reactions using a variety of nucleophiles, however, the B&F has its reactions stated in a more systematic way that is more useful than Ege's arrows that are going from here to there; it's lacking the important and helpful mechanism steps;
Graphics with space-filling models (solvent effect) were a major plus (any computer-generated graphics);
Resonance contributing structures of 1-phenyl ethyl cation was introduced too soon;
The "A look ahead" for this chapter was clear and I found it more useful than B&F.
Problem-Solving skills section- the question & answer section was helpful to check knowledge in a quick way and there should have been more than one;
Fig 7.1 "Comparison for free energies of activity for bimolecular substitution reaction" was a very clear figure;
E1 reaction was already introduced in the substitution section (7.3);
Fig. 7.4A were clearer tables than B&F's tables 8.4-8.7'
It appears that Ege has its text less divided; B&F has more divisions, so it's easier to look something up;
B&F has a section "Subst. Versus Elimination" +
B&F has sections on "Differences between E1 and SN1/E2 and SN2" + B&F has an emphasis on polar and aprotic solvents, whereas Ege did not;
More problems in the back for Ege would be helpful;
Biological leaving groups and Sulfonate esters had a special separate section in Ege, which I found to be unnecessary;
Overall, I like B&F because of its organizations, comparisons between substitution and elimination and its layout is mechanically better.

Ege (Ch 7) // Brown and Foote (Ch 8)
Likes: Ege shows more mechanisms with different nucleophiles as examples and the graphics are larger and easier to read. In B&F, the mechanisms are better organized and labeled.
Ege does not have a summary of reactions at the end of the chapter, which B&F does, and I find that a very useful study tool.

Ege (Ch 7) // Brown and Foote Ch 8)
Commentary:
Ege attempts to answer student's questions as it arises within the text and not by Brown & Foote's method through homework or sample problems. It attempts to intercept questions that might occur in the mind of students as they are learning new concepts. It incorporates comparisons as soon as a perceived conflict or similarity occurs.
Things I liked:
Both texts are fine, but I would have had an easier time with Ege, particularly since reactions were already introduced in Chapter 4 entitled "Reaction Pathways". We did learn reaction rate concepts in general chemistry, so it wasn't difficult to understand Brown & Foote. But comparing Ege and Brown & Foote, I believe Ege's chapter was more streamlined without necessarily explaining all aspects of reaction rates as it was already covered earlier.
This chapter did a better job addressing solvent effects. The information was located in one section whereas Brown & Foot addressed this issue in two separate sections several pages apart.
It also did a better job at presenting elimination reactions than Brown & Foote which neglected to discuss E1 reactions in any length.
Things I didn't like:
This chapter incorporated biological molecules' leaving groups. This should have been left out as it complicates the presentation of the chapter. There are later chapters that are devoted to biomolecules so I feel it is unnecessary to start introducing complicated molecules in the first quarter of the textbook.
Brown & Foot had more white spaces on each page, hence its not as intimating. The text, problems and figures are crowded with little graphic distinction to delineate sub headings and sections and problems. Visually, reading this book for too long would strain my eyes.
I prefer seeing some example questions within the text as in Brown & Foote.
Brown & Foote's Substitution vs Elimination section was very helpful, but, surprisingly, a similar chapter was missing in Ege's chapter.

Ege (Ch 14/15) // Brown and Foote (Ch 17)
layout of the text: I would give B&F a B and Ege a B as well. B&F is not that bad but as mentioned 100 times they can always use more color and visuals especially regarding the mechanisms. Ege actually seems pretty boring, but I like the big green boxes with mechanisms they capture your attention. clarity of the presentation: I would give B&F an A and Ege a A. Ege seems pretty well organized sections especially their section on esters. logical organization of the material: I would give B&F an A and Ege a B-. I don't like the fact that Ege splits up this chapter into two separate chapters. overall usefulness as a text for this course: I think I would give B&F a B and Ege a B as well. I think B&F can be a little more descriptive in certain areas such as previously mentioned topics. I would not recommend Ege. This book is not much better than ours. It actually seems very boring and the table at the end of the chapter does not describe rxns.

Ege (Ch 14/15) // Brown and Foote (Ch 17)
Reasons and comments:
Introduction was well done;
B&F goes straight into the functional derivatives including nomenclature and structure; Ege has a section for properties of the functional groups in carboxylic acids and their derivatives (physical properties);
No space filling orbitals;
I like the divisions in B&F better; functional group by group, section by section;
No mass spec info;
Mechanisms are vaguely presented without any step-wise mechanisms;
Includes biological importance, which I think should be in a different section, like B&F's chemistry in action;
Transesterification goes very much in depth, unlike B&F;
Tables used to summarize reactions to prepare acids and on how to interconvert acids and acid derivatives +;
There should be more problems in chapter 14;
I think that chapters 14 and 15 should be combined because it seems like the synthetic transformation section in 15 still belongs to14 and that 15.3-15.5 should be in a separate "biological" section;
The organization is therefore not very logical, although B&F does jump around a lot from functional group to group, it seems more clear;
Tollens reagent was introduced in chapter 14; in B&F it was with the aldehyde and ketone chapter;
A number of reactions seem similar to those in lecture; a good example is section 14.3B; I think that the more samples of reactions, the better;
Overall, Ege presents its information really in depth; B&F more condensed.

Ege (Ch 14/15) // Brown and Foote Ch 17)
I finally found a book that Brown & Foote beats with regards to this the topic. The graphics, clarity of presentation, organizational method and ease of access to materials in Ege was just too poor. The text is dull to the eyes unattractive and not motivating at all.
The first obvious poor presentation of the text material that I noticed was the generalization of each sub-topic. Foe example, there was a sub-topic like "Rxns of Carboxylic acids and Acid Derivatives with alcohol as nucleophiles" But in Brown & Foote, sub-topics referred to the rxns of each derivative with other reactants. Mechanisms were also clearly provided for easier reference than in Ege.

Ege (Ch 14/15) // Brown and Foote Ch 17)
Commentary:
In general, after reading Ege isn't necessarily the easiest verbiage to read, but it certainly runs smoothly. Often, there are transition statements/questions that gently guide the reader to the next topic. Brown & Foote is employs only subheading within each section to introduce another topic.
Things I like:
Table 14.2 synthesis graph is very helpful.
The text describing the mechanism is much more lucid than in Brown & Foote.
Synthesis questions are GREAT!!! It provides a step by step plan toward approaching synthesis questions. This gives students a different focus when learning mechanisms. Instead of memorizing them as "vocabulary", they would be memorizing them within the context of other reactions.
Things I don't like:
This chapter includes biological molecules. There are later chapters that are devoted to biomolecules so I feel it is unnecessary to start introducing complicated molecules in the first half of the textbook.
I prefer Brown & Foote's treatment of carboxylic acid reactions in one chapter then the derivatives in another. Ege intersperses carboxylic acid reactions with derivatives.
The presentation of graphics and the type setting is not easy on the eye. Brown & Foot had more white spaces on each page, hence its not as intimating. The text, problems and figures are crowded with little graphic distinction to delineate sub headings and sections and problems. Visually, reading this book for too long would strain my eyes.

Ege (Ch 14/15) // Brown and Foote Ch 17)
B&F Structure & nomenclature better more useful.
B&F good generic reaction discussion/mechanism.
Ege puts mechanism off until it is too late to be effective.
Ege makes a good point of pointing out deprotonation of resultant acid during base hydrolysis.
B&F discusses each carboxylic acid derivatives separately (useful)
Ege- too busy; mechanism/processes need to be set off from text.
B&F -more concise.

Ege (Ch 20) // Brown and Foote Ch 20)
Comments: Ege-Bad intro paragraph. Needs more detail to set up discussion.
Takes too long to get to real discussion of why nucleophilic substitution takes place.
Better mechanisms in B&F. They take the mechanism step by step.
Ege has better graphics regarding resonance stabilization/directing effects but B&F sets those off better from the text.
Ege is good at synthesis considerations going step by step through the reasoning process.

Ege (Ch 20) // Brown and Foote (Ch 20)
Positive remarks for Ege: I preferred the use of circling the positive charge on the benzene ring when showing the delocalization of charge. Ege always seems to present the material in a way that is easy to comprehend, with great problem solving skills.
Negative remarks: the tables presented in the chapter for o,p-directors/activating could not compare to that of B&F. Highlights of new terms to the side of the page would have been good, as in B&F. Positive remarks for B&F: Fantastic representation of tables and material.
Overall, it was a well organized chapter.

Ege (Ch 20) // Brown and Foote (Ch 20)
Likes:
Well layout and organized. It goes from one eletrophilic reaction to the next in an orderly fashion.
Table 20.1 of the directing/activation is better organized than the one in Ege.
The "key reactions" at the end are of the chapter, for the same reasons as before.
When refering back to reactions or concepts in previous chapters it references the chapter and section making it easy to go back and review if needed.
Dislikes:
Missing some of illustrative mechanisms of reaction, i.e. mechanism for SO3/H2SO4.
Overall:
Both textbooks have their strengths and weaknesses. But I would choose the book by Ege, eventhough I have only sampled two of its chapters. I find Ege to be easier to read and it uses a lot more visual aids in its discussions.

Ege (Ch 20) // Brown and Foote Ch 20)
Ege includes sulfonation mechanism including all resonance forms whereas B&F does not show the mechanism at all. The mechanism for nucleophilic substitution in Ege is shown in much more detail than in B&F. In this chapter Ege does include a summary of reactions which shows intermediates. In my opinion Ege is the better book for this chapter.

Ege (Ch 20) // Brown and Foote Ch 20)
Like I already said, the graphic used in Ege were very dull to the eye and not motivating to a good extent. Also, the presentation in CH 20 is better than that in CH 15 of Ege's text, but the entire presentation is not as good as that in Brown & Foote. Also, the presentation of other rxns such as reduction and oxidation of the compounds are more and easily accessible for reference purposes in Brown & Foote than in Ege
Both books had their various focus points and areas but in general, I find the material more interesting, straightforward and reader friendly in Brown & Foote than in Ege.

Ege (Ch 20) // Brown and Foote Ch 20)
a) Things I liked:
The graphics were good and as above I liked the background coloring for the "visualizing the reaction".
b) Things I didn't like:
Problems in the middle of the chapter are OK by there was a lack of example problems with solutions worked out.
I think some of the figures should have included more explanation with the figure - that would make them more stand alone. I think B&F did a better job at this.

Ege (Ch 20) // Brown and Foote Ch 20)
Commentary:
In general, after reading Ege isn't necessarily the easiest verbiage to read, but it certainly runs smoothly. Often, there are transition statements/questions that gently guide the reader to the next topic. Brown & Foote is employs only subheading within each section to introduce another topic.
Things I like:
Ege placed the Nitrogen and Sulfur Reactions after the Friedel-Crafts. It flowed better than in Brown & Foote which also seems to place nitrogen and sulfur reactions in the oddest places. It almost appears that Brown & Foote would just slap on a remotely similar nitrogen/sulfur reaction adjacent to the carbon counterparts. If they had to intersperse amino thiol reactions, they should have decided to put it at the end.
I also liked the occasional rhetorical question in Ege's chapter, which served as a transition from once topic to another.
Synthesis questions are GREAT!!! It provides a step by step plan toward approaching synthesis questions. This gives students a different focus when learning mechanisms. Instead of memorizing them as "vocabulary", they would be memorizing them within the context of other reactions. I prefer to have a synthesis discussion within the text instead of just as a homework section at the end of the chapter as in Brown & Foote.
I also like the fact that the answers are always located on the next page so you have the chance to work it out without being too tempted to look at the answers right away.
Things I didn't like:
The presentation of graphics and the type setting is not easy on the eye. Brown & Foot had more white spaces on each page, hence its not as intimating. The text, problems and figures are crowded with little graphic distinction to delineate sub headings and sections and problems. Visually, reading this book for too long would strain my eyes.

Ege (Ch 20) // Brown and Foote Ch 20)
layout of the text: I would give B&F an A and Ege an A as well. Ege and B&F both lay out what we need to know however Ege also includes some neat history (buckminster fullerence). clarity of the presentation: I would give B&F an A and Ege a B. B&F places certain topics with each other such as nitration sulfonation then presents other topics whereas Ege splits up topics for no reason (ex: show how make nitronium ion as opposed to just including it in the mechanism when it actually occurs). logical organization of the material: I would give B&F an A and Ege a B-. I followed B&F well as it present all rxn then spks about effects substituents have. Ege presents a rsn then spks about orientation in electroph. subst. then presents friedel and crafts. This does not seem very organized to me. overall usefulness as a text for this course: I would give B&F an A as far as this chapter is concerned and Ege a B-. It jumps around and they need more visuals.

Ege (Ch 22) // Brown and Foote (Ch 21)
Remarks on Ege: The summary of reactions was great in terms of showing the basic outline of each reaction. However, it would have been beneficial to have shown an example and an explanation as well. Remarks on B&F: this chapter would have been better if there was additional detailed information of mechanisms. B&F tends to ignore this at times which can be frustrating.

Ege (Ch 22) // Brown and Foote (Ch 21)
Brown has much better graphics and more color to catch the eye. Brown's connections to "real life" keeps student interest.

Ege (Ch 22) // Brown and Foote (Ch 21)
Reasons and comments:
B&F has a more systematic and logical order of its text;
B&F has clear explanations of Hoffman/Cope eliminations, unlike Ege;
Ege seems (again) more in depth than necessary;
Azo dyes section in Ege is too complex and shouldn't have been too in depth;
B&F has a systematic way of presenting its nomenclature; more organization (systemic and common naming);
B&F include the purification and separation of compounds, which was not quite emphasized on in class (except for one concept question); it was not helpful for quizzes/exams; Ege does not include this info;
Ege has a good explanation of the Sandmeyer reaction;
Titles of sections in B&F are clearer and more straightforward/direct, so it is easier to look something up for future reference; with Ege, I kept having to flip the pages back and forth;
B&F's section 21.9 was a major plus compared to Ege (reactions with nitrous acid);
I noticed a mass spec problem in the back, but it was explained in the text;
Overall, Ege has a lot of emphasis on biological structures, which makes the chapter more in depth and long than necessary.

Ege (Ch 22) // Brown and Foote Ch 21)
Ege-horrible intro. This is crucial to rest of chapter. B&F sets up the rest of the chapter including reations by discussing Basicity, orbitals, etc. This is more logical than throwing student in like Ege does.
Ege-All over the place. Discussing biological compounds before basic reactions?
Ege-Messy, no structure.

Ege (Ch 22) // Brown and Foote Ch 21)
Liked: Ege did have 3 tables to sum up the rxns which was similar to Brown and Foote's Key Rxn section, and is very helpful.
Didn't like: The listing for the o,m,p directing was not clear on what all the molecules were, as Brown and Foote labels each one.

Ege (Ch 22) // Brown and Foote Ch 21)
Most of my comparison of these chapters will sound like my comparison of chapters 14 and 15 of Ege with chapter 17 of Brown and Foote.
Again, the different sections of the chapter are not divided clearly enough for my taste.
2 ) The problems in the back of the chapter could be better and more relevant.
There were several things that I found to be an improvement over Brown and Foote:
The reactions where the diazonium ion is used were explained much better in Ege. I can't really point to anything specific, but I can say that the presentation of the material seemed much more clear to me.
2) The nomenclature section of Ege is ten times better than our text! I wish I had looked at this book before the exam. Our text just seems to make a mess of this section for the amines.

3) Excellent reaction summary section!
4) "One Small Step" sections- could be interesting
Biologically active amines- This was a great inclusion in the Ege chapter! It's nice to read about connections that organic chemistry has to the real world, rather than just reading about orbitals and memorizing reactions.
For Brown and Foote I must say that the amines chapter was a horrid mess, especially the nomenclature. Of course that could have more to do with me than with the text, but I think that other people had trouble too.
After now having read all of three of the assigned Ege chapters, skimming other parts of the text and comparing them with our text, my opinion is that in general the two texts are very comparable, with the exception of the amines chapter in which Ege is far superior in its presentation, specificity, and clarity. The following would be the grades that I would assign the two books on the basis of the amines chapter only.

Ege (Ch 22) // Brown and Foote Ch 21)
Commentary:
In general, after reading Ege isn't necessarily the easiest verbiage to read, but it certainly runs smoothly. Often, there are transition statements/questions that gently guide the reader to the next topic. Brown & Foote is employs only subheading within each section to introduce another topic.
Things I like:
The best attribute to Ege is the "Problem Solving Skills" section. This section seems to occur in every chapter. It provides a step by step plan toward approaching synthesis questions. This gives students a different focus when learning mechanisms. Instead of memorizing them as "vocabulary", they would be memorizing them within the context of other reactions. I prefer to have a synthesis discussion within the text instead of just as a homework section at the end of the chapter as in Brown & Foote.
Things I didn't like:
Biologically Active Quaternary Nitro Compound section was placed within the main text of the chapter. There are later chapters that are devoted to biomolecules so I feel it is unnecessary to start introducing complicated molecules within this chapter. If need be, Ege should have separated this information as Brown & Foote does with their "Chemistry in Action" section.
As with the other chapters, not many mechanisms were elucidated on the text.


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