A Tale of Two Textbooks, Then & Now — RVW #2

June 6th, 2007

In the second part of his series, Retread lays out his first impressions of Jones vis-à-vis his previous orgo text in grad school, English & Cassidy.

The book for my first Organic Chemistry course (’58 – ‘59) was English and Cassidy, 2nd edition, ‘56.  Jones is the 2004 edition.

………………………………………English & Cassidy            Jones

Pages (text only)                442                          1323
Page size  (inches)            9 x 6                         10 x 8
Text width                          4.5                           5.25
Text height                         7.0                           8.50

The most striking difference is the graphics.  There were only six 3-dimensional representations in the first 100 pages of Cassidy, while Jones has TNTC (too numerous to count).  It is hard to find a page in Jones without one.

The tone is completely different.  Jones is chatty and conversational.  “Remarks for the Student” in E&C begins as follows:   ”It is usually taken for granted that the student who  takes up the study of organic chemistry has a thorough knowledge of first-year college chemistry.”  Not too warm and fuzzy.

One of the very best things about Jones, is that he tells you what is hard, and what you must learn. “The (R, S) convention looks a bit complicated.  It is easier than it appears right now, but it just must be learned and cannot be reasoned out.”   Repeat this advice 50,000 times and you’re through med school.  There is no reason the appendix is on the right, the heart is on the left, speech is usually in the left hemisphere  etc. etc.  Jones also tells you what looks  hard but really isn’t — drawing cyclohexane in the chair form for instance.

Another very good thing about Jones (which may seem rather trivial) is that when he points you back, he gives you a page number to go to.  On retirement from medicine, I indulged a lifelong taste for math by auditing some math courses (number theory, abstract algebra,  algebraic geometry) at the local colleges.   Math books almost never repeat anything.  You are referred back to theorem 10.3 (and have to hunt for it).   There are hundreds of theorems, corollaries etc. in the average upper level math book.  It gets irritating unless you have a completely flawless memory.

Also, math books don’t usually tell you what’s really important, and what will be used later.  Not all results are equally crucial for the argument.  On reading it for the first time, you can’t tell the wheat from the chaff.  Jones is excellent at this.

In one sense, the two books can’t be compared, just as stereos back then and now can’t be.  I worked all summer as a supermarket checker at $1/hour before entering college in ‘56 and bought an RCA Victor record player to take with me for $140.  The richest man in the world back then could not buy sound of today’s quality no matter what he was prepared to spend.

However today’s convenience store worker would have to work considerably more hours to buy Jones (167.74) and the answer book (80.59) than I would have had to for English & Cassidy back then.  I asked the student checking me out how anyone could afford books like
these.  He said that often students bought a single textbook and shared it.  Shades of the 19th century Ghetto.  My grandfather told me how there were people who could only read Hebrew upside down, or at a 45 degree angle, because 4 – 6 students would sit around the  same table and study the same page at the same time.

One final point.  Despite the dryness, formality, lack of graphics etc. etc. not much harm was done.  I liked the book back then as did most of us.  This includes Jones himself (Yale ‘59), who almost certainly used the book, as English and Cassidy were Yale professors and the first edition came out in ‘49.

Previous Comments

  1. Elwoodcity Says:
    June 6th, 2007 at 9:46 am My advisor is always complaining about new textbooks being in an arms race of adding bells and whistles that distract students instead of presenting the actual chemistry simply. I think that Jones is a Master at striking the right balance, and I’m glad his was the book that Excimer recommended first.
  2. Darksyde Says:
    June 6th, 2007 at 1:20 pm I don’t know R,S at all. Which is probably why I’m a biologist now. Everything to me is D,L. Biology doesn’t care about optical rotation (no matter how much the chiral-light-origins-of-life people try to spew out BS). However, Jones was the book I learned from, and it’s great. I love the self-referential Jones textbook on the desk in front of the chalkboard with the tropilium ion.Let’s not rag on all math books. Some of them are good. I think the math equivalent of Jones is Munkres, Topology. He explicitly lays out the important thing, has lots of pretty pictures, and says stuff like “Urysohn’s lemma is one of the most important theorems…”
  3. Joe Reilly Says:
    June 6th, 2007 at 4:46 pm I’ve never used Jones, but I was a huge fan of Wade during orgo. Anyone have an idea of how the two stack up side by side?
  4. Paul Says:
    June 6th, 2007 at 6:35 pm We used Wade (2nd ed.) in high school. It’s much less conversational and much more no-nonsense than Jones.
  5. provocateur Says:
    June 6th, 2007 at 7:44 pm nobody likes morrison and boyd..hmmm
    not tht i like it but i heard its popular in asia..
    and when u mean ‘jones’ its maitland jones, rite??
  6. Jose Says:
    June 6th, 2007 at 7:51 pm If you want a book that heavy on whiz-bang and *lite* on substance, check out the Bruice tome. Lots of errors have been propagated through multiple editions, and the price tag is nauseating. But hey, what else can you expect when you’re working the pre-med market?
  7. Asian Says:
    June 6th, 2007 at 10:59 pm To #,Frankly, now only I came across the Jones! My Bible was Morrison and Boyd, whose popularity is partially due to the low price(d edition here). I never considered March as a text book, for me it is a reference book.
  8. Asian Says:
    June 6th, 2007 at 10:59 pm To #5,Sorry, a typo there.
  9. Ψ*Ψ Says:
    June 6th, 2007 at 11:06 pm I am curious as to where you bought the book.
  10. Asian Says:
    June 6th, 2007 at 11:22 pm To #9,
    I assume your question is directed to me. I donot know how to answer it in your prespective. These so named ‘low priced editions, only to be sold in countries – – – ‘ can be bought from any accademic book stores in these countries.
  11. Ψ*Ψ Says:
    June 7th, 2007 at 12:25 am Oops! That was actually directed at Retread.
  12. excimer Says:
    June 7th, 2007 at 1:53 am Personally, I used McMurry as an undergrad, and I liked it. It was pretty good at explaning things (annoyingly lite on mechanisms sometimes, though) and pretty low on unnecessary crap. However, after getting a copy of Jones’ text from a prof cleaning out her bookshelves, I realized that that was the superior text. Textbooks are an industry in and of themselves, hell-bent on screwing students over as much as possible. It doesn’t matter where you buy your books, they’re still twice as expensive as they need to be. Constant new editions keep students from selling back perfectly good copies of texts that only change the garbage and little of the pertinent information. It is highway robbery, for the most part. Professors that are too lazy to not care what textbook one uses, or at the very least, treat older editions of the text as perfectly good, are also part of the problem.For analytical chemistry, nothing beats Harris’ book.
  13. Paul Says:
    June 7th, 2007 at 2:48 am Does anyone know a good instrumental analysis book?
  14. kiwi Says:
    June 7th, 2007 at 3:21 am as in Silverstein? MS, IR, NMR all covered nicely, but not more esoteric techniques. Very good appendices for research use, more tables than you can shake a stick at.http://www.amazon.com/Spectrom…..amp;sr=1-1
  15. Greg Says:
    June 7th, 2007 at 9:52 am I learned from Morrison & Boyd from an edition way out of print by now. Textbooks have come a long way. I teach from McMurray now and it’s a fine book for the large, mostly non-major, organic chemistry class. If I were to teach a majors section I would definitely use Jones. I love his mechanistic approach.
  16. Retread Says:
    June 7th, 2007 at 10:55 am Thanks for the comments. Looking at the times of the postings I wonder if some of you ever sleep. Darksyde’s comment was the most interesting to me, but the response is pretty tangential so I’ll save it for last.Paul — that must have been a pretty fancy high school you went to if you had organic chemistry there. Mine was quite small — a graduating class of 48, of which half were girls (none of whom went to college). However, there were advantages, as you didn’t have to specialize — one of my kids in a high school of 1500 was told that he could be a musician or an artist, but not both (he chose art). Most of my friends back then were on the basketball team (our school wasn’t big enough for football), class officers, in the school play, on the school paper, on the school annual etc. etc. E.g. all of the above, just like I was.Provocateur — yes it’s Maitland JonesPsi * psi — I bought the Jones etc. at the college bookstore of same state school I audited the math courses.Darksyde — I didn’t rag on all math books, just the usual ones. One of the reasons for auditing the math courses (what good would a grade or another degree do for a guy my age) was to finally understand the math we are all exposed to as chemists. We had a quantum mechanics course in grad school back then and I did well in it, but I felt that what I was doing was just like my Bar Mitzvah — mumbling incantations in a language I didn’t understand. Surprisingly, some of my friends (a cousin who was a math major now a computer jock and a guy who went through Harvard in 4 years but picking up a masters in Physics as well and who now has a business making optical instruments for NASA and various physics departments) feel the same way.
    Parenthetically, that’s one of the joys of chemistry. I think we develop a deep intuition about what those little guys are doing down there. Why? Because we can predict things — not perfectly, but more often than not. A synthesis is basically one chain of successful predictions (among the many unsuccessful predictions — but the number of unsuccessful predictions is vanishingly small compared to the number of predictions which could have been made)

    We used Dummit and Foote in the yearlong graduate math course I just finished auditing. I think Rotman’s book “Advanced Modern Algebra” is better — the proofs are shorter and some undefinable way cleaner. I’m presently working my way through it. Like Jones, Rotman adopts a pleasant conversational tone. The book has 11 chapters. Theorems and examples are numbered sequentially. Chapter 7 ends with Theorem 7.105. So there are > 1000 things to refer back to in the course of the proofs and discussions — none of which have pages to go to. It gets pretty tiresome.

    Another point about Rotman — normal subgroups are introduced by the properties they have. No mention is made of how important they are. Eventually you see this, because normal subgroups let you factor groups into smaller ones similar to the way primes factor numbers. None of the introductory abstract algebra books I’ve looked at (at least 10) tell you who invented them (Galois) or why. A fairly bizarre definition is given, properties follow logically etc. etc. It is not satisfying on a first exposure. Hopefully Munkres is quite different.

  17. Milkshake Says:
    June 7th, 2007 at 11:00 am How about the worst available mainstream organic chemistry textbook? I would vote for Amos Smith the thirdest. I think his textbook is perfectly awfull. (Back in Prague we had something similar, it was universally known as “The green Monster” and the joke was that the only concievable use for such book would be to drop it on its authors from a library roof.)
  18. Hap Says:
    June 7th, 2007 at 11:17 am I don’t think it’s a bad textbook, but the students in the same org. chem. class as me uniformly despised Kemp and Vellachio (which is sort of ironic, because Kemp was viewed as one of the best teachers there). It is highly mechanistic, and it seemed sound – I think it was disliked because it wasn’t easy to read. The colors in MoBoyd are neat, but it seemed lighter on mechanism than I would like.
  19. DrSnowboard Says:
    June 7th, 2007 at 11:38 am Undergrad text was Streitweiser and Heathcock here in the UK way back in the mists of the 80’s.
    Never ever liked March, meaningless attempt to overcomplicate and overcategorise, bit like Patai’s (or should that be Rappoport’s ) ‘chemistry of functional groups’. Dire.
    Disconnection Approach by Warren was far more useful.
  20. syregnask Says:
    June 7th, 2007 at 1:15 pm My first organic chemistry course was taught using McMurry’s “Fundamentals of Organic Chemistry”, but at the first lecture the professor was so nice as to recommend the unabridged version “Organic Chemistry” (4th ed) for those of us interested in a little more. As I didn’t already have the book I followed this recommendation. I absolutely loved the book – granted, I may have been biased by loving the subject, but it did serve as a welcoming introduction to the subject for me.
    My second organic chemistry course was taught using Morrison & Boyd’s “Organic Chemistry” (I forget which edition) – this book initially struck me as a little more dry than McMurry’s, but not very different in content. They do have humour, though – as one will discover if one carefully goes over the problems in the book.
    My third organic chemistry course was taught using Carey & Sundberg’s “Advanced Organic Chemistry, A & B” (3rd ed). I have to say that the first time I read these 2 books I really didn’t appreciate them very much at all. But when I read them a second time getting ready for the exam I started to see them making sense and actually felt that they were really good.
    I guess this was around the time Clayden, Greeves, Warren, & Wothers released their “Organic Chemistry” and virtually everybody I knew (in organic chemistry) started hyping it’s greatness. Of course I got my own copy and read it. And I must say that I agree – it is good.
  21. Darksyde Says:
    June 7th, 2007 at 2:15 pm Funnily, Wikipedia does mentions in the first sentence why normal subgroups are so important. Dummit and foote is passable (but not great), but yeah, “Advanced Algebra” did look much better (never used it).What annoyed me about math was the increasing tower of definitions that get created. I couldn’t keep them in my head, just as I can’t keep sports teams or players (or reaction names) in my head. Eventually I was talking with people who were having chats about “sheaf automorphism conjugacy subclasses” and at that point I was lost. On the other hand I think I have a fairly good conceptual memory, which I think suits me for what I’m doing now.A friend of mine just wrapped up his math PhD (at UCLA; he proved a moderately important theorem) but he was so beaten down by the difficulty of innovation in math — and competition with prodigies — that he joined the navy and is now finishing basic training, and getting ready for pilot school.
  22. JSinger Says:
    June 7th, 2007 at 6:06 pm I’m a week or two behind on this chain of events, but Retread’s newfound enthusiasm prompted me to share my story:I took organic chemistry as a bio major requirement. I loved the labs (did badly as like a lot of scientists I have good hands but no patience for pointless undergrad lab notebook keeping) but hated the class, probably because I let the premeds scare me into memorizing because understanding was supposedly too hard.I got my molbio PhD and eventually wound up in a pharma job. While getting oriented there, I found In The Pipeline which was an invaluable help, but which also led me to Tenderbutton and then to the other chemistry blogs. And now to pulling out my old orgo textbook and trying to learn it right this time.Like Retread, I love the delight and irreverence of the chemistry blogs. It’s a shame that all the biologists either write whiny, bitter “Female Woman Scientist Grrl” blogs or give in to the cheap pleasures of ranting about creationism at ScienceBlogs.
  23. provocateur Says:
    June 7th, 2007 at 10:34 pm retread
    how abt finar???i guess nobody heard abt it here….
  24. Asian Says:
    June 7th, 2007 at 11:42 pm Finar was very popular in India, once upon a time. But at my time its fame has been started fading for obvious reasons.
  25. rb Says:
    June 8th, 2007 at 8:53 am milkshake:amos smith has an organic textbook?
  26. Retread Says:
    June 8th, 2007 at 10:59 am Glad to see all the interest in the comparison and in introductory organic books in general. There will be another pair of posts coming up (but much later) between Edwin Gould’s “Mechanism and Structure in Organic Chemistry” from ‘59 and Anslyn & Dougherty ‘06. Much later, because I’ve got to get a lot farther in Jones before tackling Anslyn which is far more sophisticated (it should be) than Jones (not a criticism of Jones which is introductory). What I’ve seen of Anslyn is very, very good.Gould was definitely the bible back then. I had the pleasure of playing chamber music with Dr. Gould himself at Interlaken in Michigan in ‘04 (before I realized who he was) — he’s a very good amateur violinist by the way.You don’t think anyone writing books 48 years ago is still active in research, but Dr. Gould is still pumping out papers. His CV mentions that he got his PhD from UCLA in ‘50. So much for ‘toxic chemicals’ shortening lifespan. I seem to remember that the guy who developed the mercury sealed vacuum pump and who was drenched in the stuff lived to a very ripe old age, and Dr. Westheimer just passed away in his mid90s. Woodward, of course, died young — but he smoked like a chimney. Not knowing anything about medicine back then we all thought he would die of lung cancer (apparently he didn’t). While smoking does raise the risk of lung cancer substantially, the really bad thing about it, is that smoking raises the risk of something far more common — vascular disease (e.g. heart attacks, strokes) quite substantially.Hap — too bad about Kemp’s book. Woodward thought a lot of him and he was a Junior fellow at the time. From knowing him, I would guess that his book was pretty uncompromising (I haven’t seen it). Everything comes easily to the brilliant and usually they don’t see why they should explain what is obvious to them. That’s what’s so good about Jones — from 30+ years of teaching he knows where all the bumps and hickeys are, and does his best to guide the student over them.Darksyde — exactly right about the tower of definitions. Rarely if ever is the historical background of the work necessary to achieve the definition given. Two examples — even though Galois essentially invented groups, their definition wasn’t formalized until decades after his death. Similarly, the first abstract definition of a field was by Weber in 1893 — according to David A. Cox in his book on Galois theory (p. 80). This was > 50 years after Cauchy’s construction of the complex numbers. So the definitions which are presented to the budding mathematician like the stone tablets from Mt. Sinai, weren’t graven initially, but carved out of some fairly unpromising material with much effort. All this is usually hidden from the student. If you have the time, look at Cox’s book — it’s 500 leisurely pages on Galois theory and its background. Be prepared — you don’t get to the fundamental theorem until p. 161

    Provocateur — I never heard of Finar, but the first edition seems to be ‘64 and at that point I’d been in med school for two years.

    Once again, thanks for all the comments — I find them quite interesting

  27. Jim Says:
    June 8th, 2007 at 12:10 pm Bug fan of the Clayden/Warren/Wothers textbook. Unfortunately, I used McMurry for my undergrad – IMHO it is quite poor.Other good texts include Carey/Sundbergh and Peter Sykes’ mechanism bible. For retrosynthesis I like “The disconnection approach” by Warren.My £0.02
  28. Hap Says:
    June 8th, 2007 at 1:13 pm I don’t really know what the problem was with Kemp’s book – as a lecturer he was really good and interesting, and his mechanistic approach was good as well. He spent a lot of time trying to teach the course well and observing the outcomes – he was one of the (few) professors to escape the curse of the Baker Teaching Award because he already had tenure.I didn’t think Kemp’s book was bad, but it seemed dry.
  29. provocateur Says:
    June 8th, 2007 at 9:45 pm why do great scientists not write text books??
    examples
    sykes…hv seen rarely any papers
    morrison , boyd…same here
    smith…not anything worth writing about
    march…again not tht great of a scientists..hopefully it changes..
    like anslyn, warren..
  30. Paul Says:
    June 8th, 2007 at 10:52 pm IMO, Streitweiser and Jencks were both great scientists. Not just good—great.
  31. excimer Says:
    June 8th, 2007 at 11:42 pm Both anslyn and dougherty are great scientists, I think. And although Crabtree’s book stunk, he is an outstanding inorganic chemist. But, contrary to his name, provocateur makes a good point, and I think one of the reasons for that is that writing textbooks is an extremely time-consuming process, and it must take a lot out of research time or tea time or whatever the hell it is professors do during the day. In organic chemistry, the big names are usually devoted to writing books on their subjects of interest that are usually used as reference books or graduate level texts. Writing an introductory organic text, by contrast, is a much more difficult thing to do.
  32. excimer Says:
    June 8th, 2007 at 11:43 pm Though Larock’s done some cool stuff, aside from writing that massive blue tome.
  33. squirmy Says:
    June 9th, 2007 at 2:12 am excimer, your post #12 hits me in a few ways.i was also introduced to Jones when a professor was cleaning off his shelves. i was really impressed with it. i wish i could use it now, but i’m sharing organic with a tenured prof…to be exact, we’re splitting 2 sections of organic I and he’s teaching the lone section of organic II, so i don’t want to force the students to buy a text they won’t be able to use in the 2nd semester.coincidentally, the text he’s chosen is McMurry. it’s ok, not great, but i was a little shocked when i requested a desk copy and they gave me the 7th edition…seeing as how, this professor is still using the 5th!! i actually got a call from the bookstore b/c they were so surprised they could still find enough copies. i understand he’s trying to save the students money, but i’ve wondered when was the last time he even thought about what book he was using.i really need to get a copy of anslyn & dougherty. i had anslyn for phys. org. and at the time we had lousy & richardson as the required text, but anslyn had his unpublished book chapters available for hourly checkout in the library (no copying allowed). even in that rough form, it made sooo much sense and was a very easy read. btw, anslyn was a great teacher and imho is a very creative scientist and a downright nice person.back to the subject of intro organic texts, i understand anslyn will also be on board for the next edition of Brown, Foote & Iverson. i’m interested to see what he brings to it.
  34. Retread Says:
    June 9th, 2007 at 7:49 am I sent the following to OrganometallicCurrent, but haven’t heard anything back. What do you guys think ?5 June ‘07I’m Retread, whose Rip Van Winkle series began in ChemBark 30 May. Organometallic chemistry has exploded since ‘62, and absolutely nothing on your site looks familiar to me. I’m working my way through Jones ‘04, and later will tackle Anslyn. Jones doesn’t even discuss metathesis. So what do you regard as the best introduction to organometallic chemistry?Retread
  35. bluebuns Says:
    June 9th, 2007 at 9:27 am hey fellas,
    i just read the whole blog last night and found the book vs book discussion interesting. when i took the intro course, the text was by seyhan ege and i thought it was the best thing since mashed potatoes until grad school. thats when i discovered kids from other schools had never heard of it and all those pre-meds i started tutoring were using morrison and boyd or jones… and that is when i learned the real trick. the best way to go is to have an old (aka cheaper) edition of all three (or three of your favorite flavours) on hand. usually the important stuff is in all three and at least one will do a good job explaining it.as for march, this tomb is downright unreadable. mine is closed for so long between reads it smells like a library when you open it. for someone who once swayed woodward to his line of thinking, i would have suggested bogers class notes and Carey and Sundberg to get back into the groove. classics in total synthesis I and II should follow and FMO theory by flemming needs to be in there somewhere if your not bored yet (a must have in the event some FMO superfan starts spouting off HIS explaination…).by the way, cuddos to paul and retread; i love that you have attracted mathmaticians, physifolks, biologists and biochemist into the frey. interdisciplinary discussion is always so nice.i didnt quite get what lit the fire under W the sames superfan’s bum…later
    bb
  36. Anonymous Says:
    June 10th, 2007 at 8:50 pm my bible for organometallic is the text by hegedus.I hv also liked crabtree but only barely.
  37. Bad Cop Says:
    June 10th, 2007 at 8:58 pm Many good OMET books out there, but I think Elsenbroich is one of the best (and there is a new edition soon!). Crabtree is near the top too, and the two OUP slim paperbacks by Bochmann are also pretty good (and cheap).
  38. Paul Says:
    June 10th, 2007 at 9:22 pm I am not a fan of Crabtree’s book. I don’t think the text explains important concepts that well and the figures are not particularly helpful.
  39. excimer Says:
    June 10th, 2007 at 11:17 pm Hartwig gave us drafts of the organometallics book he’s helping write (it’s the old green book, four authors, I don’t remember their names) and they’re quite excellent, though I have no idea when it’ll be published. They were very rough drafts- the figures were either chemdrawn or hand drawn. Still, far better than Crabtree’s. Be on the lookout for it.
  40. excimer Says:
    June 10th, 2007 at 11:21 pm oh i think it was collman hegedus norton and finke.
  41. DrAmazon Says:
    June 13th, 2007 at 9:11 am I teach orgo at a small liberal arts college. We use Solomons & Fryhle. I have taught from Vollhardt, McMurray and Brown and Foote. Vollhardt is a challenging text for most undergrad non-majors. McMurray is nice in that it gets to the point and is not overly verbose, which students like, but is perceived by some to be “light”. Brown and Foote is also considered “light” but recent editions have more meat. Solomons seems to be between McMurray and Vollhardt for level.I like Bruice and Janice Smith’s new text. Yes, the new texts are very heavy on graphics and textboxes-most of my students do not read a textbook the way many of us read a book or article. Most are heavily visual learners with short attention spans so the graphics help them a lot.RVW A couple of great supplementary texts are Organic Chemistry as a Second Language by Klein (good reinforcements of all 1st semester topics) Pushing Electrons by Weeks (a primer on writing good mechanisms) and Electron Flow in Organic Chemistry by Scudder (more advanced, but an excellent distillation of the essence of mechanism).
  42. TJ Says:
    June 13th, 2007 at 4:15 pm Kemp wrote two monographs that he used as his text back in the 1970’s. They were printed by MIT and sold in the COOP but were never published as a textbook for wide distribution. These were gems and are well worth tracking down . I got to know Kemp pretty well, since he was my thesis supervisor , and was around when he was writing his text . The publisher insisted upon changing Kemp’s notes into a standard format to compete with tha standard texts of the day , so essentially it lost all the charm upon becoming Kemp and Vellachio. I never knew what the latter did to merit co-authorship . He was another grad student at the time and I think spent a summer helping get the manuscript together. Dunno .Kemp was and I hear still is a great teacher .


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