Talk:Organic Chemistry

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Hi! I just reviewed your book, updating your development stages . Wow! This took some time, cause it is really a BIG book with many many sub-chapters! I was impressed by the quality and clear style of writing. Keep up the work, and concentrate on the 75% chapters: I think many of them can be 100% by just finishing up the pages or including those examples that have been announced, but obviously forgotten... (See Help:Development stages for how to use this template, and if you read this, help by reviewing another book and spreading the word! Thanks!) --Andreas Ipp 23:30, 12 Jan 2005 (UTC)

I'll work on this again in the fall when I'm in the mood for organic again --Ghostal 23:00 EST, Apr 11, 2005

Contents 1 In module Ketones and aldehydes 2 New icons 3 Official Headers / Footers 4 Standard Structure Format? 5 Wikibooks:Naming policy 6 Print Version of this Wikibook 7 A page move 8 Duplication 9 Some reorganizations 10 Standard chapter structure? 11 Chapter structure 12 Ethers 13 Index 14 An outdated and copycat organisation 15 Organisation 16 Content 17 Cost 18 Image Warning 19 Image Warning 20 Image Warning

[edit] In module Ketones and aldehydes

I suggest that the topic "Preparing Aldehydes and Ketones" should have subtopics of "Preparing Aldehydes" and "Preparing Ketones". Not all of the preparation methods can be used in both instances. It would help with clarity. Glich (talk)

[edit] New icons

I have uploaded to the Commons two pictographs that I made: , . They are both public domain. Ramir 13:19, 31 May 2005 (UTC)

[edit] Official Headers / Footers

Hello all! This is an amazing book so far, and I look forward to editing it. I'm curious which pages include the 'official' Header and Footer (including the little ethane icon). I'd be happy to standardize as many as I can, but I need to know which you prefer for the standard.

Cheers! Buxtor 22:44, 2 June 2005 (UTC)

[edit] Standard Structure Format?

Hey All! There's really quite an impressive array of work here. I'm concerned, though, that there's no nice standard way to display chemical structures. While we don't have the same engine as the math guys do for displaying sturucture like they do equations, we can still try and settle on one program and settings for making structures, no? I'd recommend Chemdraw, ACS template with the bold width 2.5 and line width 1.5. --Lineweaver 08:46, 23 December 2005 (UTC)

[edit] Wikibooks:Naming policy

Great work you are doing here. However I must suggest you have a look at the Wikibooks:Naming policy.

--Krischik ^T 07:55, 16 January 2006 (UTC)

Indeed, I shall berenaming all pages in this book so that they start with "Organic Chemistry/". This will make this book consistent with most other wikibooks, plus allow for easier navigation. I trust this change will be non-controversial (especially as it is being done in a way that preserves all links), Jguk 12:41, 20 February 2006 (UTC)

[edit] Print Version of this Wikibook

If you look at Organic Chemistry/Print Version, I've put together a compilation of most of the pages for this Wikibook. I have excluded pages that have not been created yet (so if you add new pages, it might be good to put them here), and I'm still working on the appendix sections.

Feel free to edit and work on this print version, but it is looking pretty nice at the moment. Don't worry about keeping the content up to date, as if you work on adding just content to the existing parts of this Wikibook it will also be updated in the print version automatically. This is done through the transclusion process. Some minor reorganization may have to be done with the various sections, and there is some duplication of a few items that still needs to be dealt with.

Anyway, have fun with this content. BTW, I'm preparing to make a PDF version of the print version, but it would also be nice to clean up the content before we make this "official". There are far too many red linked images, and I'm not sure exactly what happened here to make them red links. I can't find any history of those images from the deletion log. --Rob Horning 17:49, 13 March 2006 (UTC)

[edit] A page move

I've started doing work on the Substitution Reactions page, but I'd like to rename the page, Nucleophilic Substitution Reactions because it's a little more accurate as well as being more descriptive. I assume this is done simply by "moving" the page. Being new at this, however, I'm reluctant to make such a change without someone saying "go ahead and do it." I read the noob stuff and it said, "be bold", but I'm drawing the line at moving a page, for the moment. --Pete 15:25, 11 November 2006 (UTC)

[edit] Duplication

The Haloalkanes page has a short section on reaction mechanisms that duplicates a lot of what is discussed (and in some cases, contradicts) in Substitution Reactions. I haven't yet gotten to the Elimination reactions page, so I don't know if there are contradictions there, but there is surely some duplication.

It's probably best to link to the Substitution Reactions and Elimination pages from Haloalkanes and move whatever is needed from the Haloalkanes page.

As for contradictions, the first thing that caught my eye (since I was updating this in the S_N2 reaction mechanism, is that in the Haloalkanes page, it says non-polar solvents are preferred. This is, as far as I know, incorrect. Aprotic polar solvents are preferred in S_N2 reactions based on nearly every book and online source I have checked. Pete 19:56, 11 November 2006 (UTC)

[edit] Some reorganizations

Okay, I've moved some stuff around a bit. I've tried to be really careful to fix all links so that they're not going to redirects or blank pages, but I have no doubt I missed something somewhere. This turned out to be a MUCH bigger project than I expected it to be.

Basically, I renamed (via a move) Alkanes and Cycloalkanes to simply Alkanes. It still has a short section on Cycloalkanes and some of this will be left there and maybe some minor changes made because it's a very short introduction to cycloalkanes.

I will add in a new section entirely on cycloalkanes, after the stereochemistry stuff which will go into much greater depth about cycloalkanes.

And the small move was Substitution Reactions was moved to Nucleophilic Substitution Reactions since that is what it was and shouldn't be confused with other types of substitution reactions.

[edit] Standard chapter structure?

Should we have a standard format for each chapter? I usually go for:

1: Methods of making this class of compound (often referring to section (3) of other chapters)

2: Properties of this class of compound (including nomenclature, uses, etc)

3: Reactions of this class of compound (often leading to section (1) of other chapters)

Ewen 10:48, 20 November 2006 (UTC)

Ewen, yeah, I think that makes a lot of sense. I assume you mean the chapters for each functional group.

Yup! Ewen 14:40, 20 November 2006 (UTC)

I haven't decided how I want to do it, but I want to bring the Nucleophilic Substitution and Elimination reactions stuff into an earlier place in the book, possibly in their own section. I'm also not happy with all those reactions being in the back of the book. Reactions should generally be with the class of compound they're with. If a reaction has been covered previously for another functional group, you just don't need to go into any depth about mechanism, as that will be covered the first time it comes up. -- Pete 14:20, 20 November 2006 (UTC)

I agree. I'd prefer that when a reaction type first occurs that it has its own section, so that it can be found more easily later. I'd prefer that to the reaction type being a sub-heading of some or other functional group chapter. Ewen 14:40, 20 November 2006 (UTC)

Precisely and I think this is how most books handle it. I mean, you go read a chapter on carboxylic acids, and in every books I think I've seen, there's a section (or actually, usually multiple sections) dealing with all the reactions related to creating carboxylic acids and reactions that carboxylic acids can take part in. Frequently, the first time that particular type of reaction is shown and it's important, the mechanism is usually laid out with electron pushing, transition states and/or intermediates... I think we need to do all that stuff. I'm all for trying new stuff, but I think the reason it's laid out in most books this way is because it makes sense to lay it out this way. -- Pete 16:30, 20 November 2006 (UTC)

As an additional note, I think we ought to move Alkenes and Alkynes an place them between Haloalkanes and alcohols. I think they should be discussed before alcoholis and I think Alkenes is probably the place to begin discussing reactions and reaction mechanisms, not haloalkanes. My reasoning on this is that haloalkanes are often used for creating different functional groups. For example, dehydrohalogenation to create an alkene. I mean, we might want to discuss halogenation of alkanes in the haloalkanes section, but I think that's probably the only thing. It's not a particularly useful reaction since it produces so many products, but that's really the only one I think would be useful there since most of the other reactions involving haloalkanes result in the creation of different functional groups that are discussed later. Anyway, just a thought. -- Pete 16:36, 20 November 2006 (UTC)

Ewen, on a related note, in regards to structure, if you look at, for example, the Alkene chapter, notice how you go to the alkene page and it simply has links to other pages. I think this is a bad way to do it. Then if you go to Haloalkanes, it's all one one page. I think having it all on one page is the better way to do it. I think for Alkenes and Alkynes and other chapters that might be laid out that way, we ought to take the information from the sub-pages and merge it into the main page.

There are alsos some things there that need reorganization. Alkenes, for example, has a section on pi bonds. Pi bonds ought to be covered in the Foundations section along with other bonding stuff. I mean, Pi bonds are certainly worth mentioning elsewhere since they play a huge role, but I think they should be introduced before Alkenes. What are your thoughts? -- Pete 20:36, 20 November 2006 (UTC)

Yup! Haloalkanes seems the way to go for structure. What sort of page length are we looking at before splitting them? Pi (and other) bonding is surely fundamental rather than a passing topic of relevance mainly to alkenes. I'll have a bash at some of these issues. I work in a different time zone to you don't I? We'll not have edit conflicts unless I stay up late or you get up very early 8-) Ewen 20:52, 20 November 2006 (UTC)

Wow, you've been busy today Ewen. I love what you've done with the Alkanes section... We might step on each other from time to time. I work from home and I sometimes get a little work in on the book during my lunch hour or something. I don't think there's too much danger, though. I'll be doing most of my work in the evenings and weekends, so the 6 hour (maybe 7) time difference should keep us from stepping on each other too often.

I've deicded I'm going to keep away from doing any big moves for a short while. I did that pretty big move of the Alkanes section over the weekend and it turned into a much bigger job than I expected (because of all the links that needed updating) and I just kinda bit off more than I think I was ready for, so I'm going to slow down a bit. I've also almost made some structural changes that I would have regretted because I didn't see some other stuff that was going on.

So, with that in mind, for a week or two, I'm just going to do additions here and there around the book, maybe a little cleanup, and just make sure I have a better feel for where everything is and how it's laid out, what's missing, what's duplicated, etc, and adding it to my To-Do List. I'm also going to try to wrap up some of the stuff I've started, like the Cycloalkanes stuff and I need to do some more work on Elimination and Nucleophilic Substitution, and then bring them together in Haloalkanes, I think. It definitely makes sense to discuss Nucleophilic Substitution and Elimination together, if for no other reason, than because they have a tendency to compete with each other and it's easier to address that with them together than it is to address it in each one separately. Anyway, just trying to give you a heads up on where I'm going, but I don't see us bumping heads too much in the near future... -- Pete 22:46, 21 November 2006 (UTC)

[edit] Chapter structure

Ewen, you originally proposed chapter layout made sense at the time, but in working on the Alkene section, I ran into problems with it. I think what we ought to do is put together a layout model somewhere off of the Outline page and then we'll use that as a basic layout model for all the chapters that are based on functional groups. Here's the problem I ran into. I was writing about the synthesis of alkenes and for dehydrohalogenation, it goes by the E2 mechanism and thus is regioselective and, depending on the alkane, can produce reliably consistent products or possibly a mix of E and Z product. The problem is, the E and Z naming isn't discussed until later in the section, which made me stop in my tracks and come here. I think we ought to consider an order like this:

1. Naming
2. Properties
3. Reactions

Properties is sort of a catch-all for everything not falling into the other two categories. Under reactions, we'd begin with synthesis reactions, followed by the rest of the reactions. But at least, at the point that you're discussing synthesis, you can name the products without there being confusion as to what the names mean. I'm also trying to cover reaction mechanisms with the reactions, as much as possible. But like I said, I think we ought to come up with a model chapter. Look around at other chapters and see if maybe there are specific things that we're not considering for these 3 categories. Maybe there should be other categories that aren't coming to mind right now. But we can then use that model as the basis for all the functional group chapters. -- Pete 03:43, 23 November 2006 (UTC)

Yes, I was thinking that too. The structure doesn't fit well with some chapters. I should have been more flexible and not imposed a structure that didn't really fit. Live and learn! Perhaps the default structure should look like this anyhow:

Introductory paragraph (no heading - puts it above the contents)

Naming

Possible structures

Properties

Physical properties (e.g. boiling point)

Chemical properties (e.g. acidity, toxicity)

Reactions

Synthesis

(other reactions)

I'm keen to list the details of synthesis reactions under their respective reactants. Haloalkanes, for example, might have a short reference to substitution of alcohols, but the main discussion is under reactions of alcohols and the haloalkanes chapter might merely reference the alcohol reaction section.

One advantage of this moving stuff around: It helps to tidy things up! There are so many sections where work is duplicated and written to very different standards. Finding one home for each section has brought them together and made the best of them all, or highlighted the need for someone to fill a gap. Ewen 06:40, 23 November 2006 (UTC)

Ewen, I think this new order makes more sense. As for reactions, I think it's okay to mention them more than once. For example, the Wittig synthesis of Alkenes, I'm going to show the reaction and write a short paragraph about it in Alkenes, but it's a reaction between an aldehyde or ketone and a triphenylphosphonium ylide. So I'm thinking, the earliest it should be discussed in detail (i.e. mechanism details) is maybe aldehydes and ketones. So, to that degree, I don't mind duplication, as long as say, the Nucleophilic Substitution and Elimination reaction mechanisms aren't covered completely in both Alkenes and Alcohols, for example. Some reactions apply to multiple functional groups and deserve at least some mention with each of those functional groups, but the degree of duplication that's been in some places is way too much.

Today is the Thanksgiving holiday here in the States, so I won't be doing much here. I'm heading off to visit my family for the traditional turkey feast and offer thanks to the native Americans for letting us steal their land and virtually wipe them out. -- Pete 13:47, 23 November 2006 (UTC)

Ewen, another thing we've forgotten is problems. Currently, there are very few problem exercises for the reader to work on. For me, this is really a low priority, but we ought to consider how they should be placed in the book. I was thinking the best way would probably be to have them as links at the end of each chapter. There would be two links: A link to the problems and a link to the answers, hopefully with explanations where appropriate. My thinking is there ought to be about 50 problems per chapter. That's a lot of work in itself, but like I said, it's low on my priorities. There are so many other things that still need work. But I didn't want it to slip through the cracks. I've added it to the to-do list. -- Pete 03:26, 25 November 2006 (UTC)

[edit] Ethers

I noticed that ethers are discussed in the module about alcohols. Might it be better to move them into a module of their own? That way, readers might be able to find them more easily. I personally would not think to look for ethers under the topic of alcohols. -- WilliamJenkins09 04:25, 28 January 2007 (UTC)

Good idea! Alternatively, we could rename 'Alcohols' as 'Alcohols and ethers'. Certainly ethers deserve a mention in the contents. Ewen 08:40, 28 January 2007 (UTC)

[edit] Index

Anybody know how we could add an index to the book? Ewen 08:40, 28 January 2007 (UTC)

[edit] An outdated and copycat organisation

Why on Earth has this book been organised by functional groups? It should be organised by reaction types and mechanisms, the true basis of organisation in organic chemistry. A functional group organisation belongs to the barbaric ages when terms such as electron density and carbocation stability were unknown. Such an organisation is a very poor effort in the twenty-first century.

Also, the book is seriously lacking in comprehensiveness. Only classically important topics are included, at the expense of overwhelmingly important modern topics such as orbital symmetry rules (pericyclic reactions), borderline mechanism in solvolysis, retrosynthetic analysis, chiral synthesis, basic organometallic chemistry etc. Physical chemistry is oversimplified. For example, entropy-controlled catalysts so important in biological systems are never discussed. In fact the whole process of kinetics is misrepresented, as is the difference and relation between rate and equilibrium (that is, equilibrium thermodynamics and kinetics).

Many experimental observations are left unexplained, such as why certain reactions proceed only at certain temperatures at the presence of a certain concentration of a certain catalyst. Catalytic mechanisms are rarely given. Overall, the book in its current form continues the long-observed tradition in chemistry textbooks of emphasising rote memorisation over logical analysis and understanding. The book is in need of major overhaul and a complete change in the organisation and outlook to make it into a truly modern organic chemistry text that actually enriches wikibooks instead of simply rehashing material from commonly available high-school texts. 59.93.198.128 08:53, 29 January 2007 (UTC)

To take your last point first: 'High-school texts' are not 'commonly available' if you can't afford them, and the scope of this book is beyond high school anyway.

We've discussed the organisation and the consensus seems to be that organising according to functional groups (the 'nouns' of organic chemistry, as it were) is preferable to organisation by reaction types (the 'verbs'). Why? It's the status quo.

Perhaps the reaction types and mechanisms organisation can be included by cross-referencing the relevant sections in the various chapters. Please go ahead and add such cross-referencing.

Your second paragraph asks about the comprehensiveness of the content: Feel free to add what you think is missing!

Ewen 10:47, 29 January 2007 (UTC)

Regular access to an internet connection and a computer is not more affordable than a low price edition or second hand version of a standard text. Also, in its current form the book is written exactly at the level of Indian high-school OChem curricula (though US curricula is probably more elementary).

Cross-referencing can not be a substitute for organisation. Where did this discussion about organisation take place? It should be reopened. It does not make sense to use functional groups rather than mechanisms, as it is mechanisms that unite OChem into a cohesive whole. Use of functional groups creates the impression that OChem is simply about memorising seemingly unconnected mechanisms of reactions of many different functional groups. I quote a professor below:

"...overall the books are criminally incoherent, much due to that substance classes rather than reaction classes form the "basis" of the chapter division [note: NOT "...the basis of the 'organization'...", since organization can only exist when the reaction classes are the basis for the discussions, the one thing that brings order to organic chemistry!]; never does anyone take a more "holistic" or just "passioned" view, to actually demonstrate the monumental versatility of the concepts discussed - and exactly the same highly vital information is left out, about how to interpret or control all the hundreds of written consecutive equillibria, or what difference it makes to use the methoxide rather than the ethoxide, or why 70% phosphoric acid is used (or, indeed, what is meant by 70%), or why precisely 780K and not 775Kis needed, or how you actually carry out a single reaction and what apparatus should be used, or how you handle and isolate the substances; or how you name those compounds that show up later than the first few chapters (when all the authors suddenly forget the previous efforts of showing completeness in presentation)."

59.93.201.127 18:26, 30 January 2007 (UTC)

I do appreciate your criticisms are well-intentioned and constructive.

If you have a problem with the content - why not write some? No amount of requests will give me, or anyone else, more time to write material. Why not use your time to add to this book instead of criticising it? You obviously have spent some time reading the book and considering its failings.

If you missed the foreword then you may have missed some of the rationale - the intention is to supersede expensive college-level texts. You're right about the cost of computing or internet access, but this book also has a printable version - it would cost no more than the printing costs to make a copy.

Your suggestion for organisation is novel and interesting (thanks for proposing and explaining it), but I'm not persuaded that it's substantially better than the system we use now. I didn't use the analogy of verbs and nouns lightly: You need both to learn a language, but vocabulary is more important than grammar (to change the analogy slightly). How can we discuss the chemical reactions before we can name the chemicals and know their physical properties?

You're right, though - I can't find any formal discussion of the organisation. Pete and I discussed whether the structure should be flatter or deeper but nobody, to my knowledge, has suggested reorganising along the lines you suggest.

Would you like to register and choose a username? I find it a bit odd writing to an IP address! You'd also be able to add pages like this to your 'watch' list which helps discussions.

Regards, Ewen 19:39, 30 January 2007 (UTC)

It takes significantly more money to print all these pages instead of buying the book. But irrespective of whether this book replaces or supplements standard texts,I think nobody will like it to become a copy of content that is already available.

As for the organisation, if the goal was to discuss nomenclature and physical properties then the best organisation would undoubtably have been functional groups. But I think you will agree that the principal objective of a general introductory OChem text is to discuss reactions, and it is here that the advantage of a mechanistic discussion arises.

Arranged by functional groups, the conversion of a halide and an alcohol into nitriles become different things, when in reality they are the same reaction, nucleophilic substitution. This separation gives a student the idea that the only way to get through OChem is to memorise the countless reaction mechanisms separately for each different class of compounds, when he would have a far easier time if only he understood that there are only a handful of basic reactions in introductory OChem and that which one occurs can be predicted (not memorised) from a knowledge of general principles and reaction conditions. Elimination of water and elimination of hydrohalide is the same reaction, but since one involves alcohol and the other halogen a student is forced to learn them separately, adding to his burden.

As for functional groups being status quo, fashion can not be the foundation of science. Writing a textbook is not less important an exercise than writing a paper, and the same principles apply. Also, this status quo is increasingly being broken and most important second level OChem texts like March, Carey and Sykes have for a very long time used reaction types as their basis of organisation. It seems meaningless to deprive beginning students from what is already considered best for their seniors. Writing a good and original textbook that not simply a conventionally-organised collage from existing textbooks with sudden and inexplicable emphasis on the author's personal interests is a difficult and time-consuming task for which I don't have the time. However this labour can be significantly lessened by the collaboration offered by a wiki system, but that first requires consensus. 59.93.162.4 07:13, 31 January 2007 (UTC)

I hope you don't me breaking your issues into some sections and deal with each in turn? Ewen 08:54, 31 January 2007 (UTC)

[edit] Organisation

Re: 59.93.162.4's comments on organisation:

Bluntly; I don't think this book will be reorganised along reaction lines unless somebody has a huge amount of time to do it. I'm not sure that the majority of readers and writers would want this to happen anyway. It's my impression, but the 'consensus' seems to be to organise the book on functional group lines. Of course you're right; progress can be stymied by consensus and the status quo, but some projects develop by evolution, not revolution. Help in evolving the project is appreciated.

I think you exaggerate the problem. We have a section on reaction types - I gues sit needs expanding and re-emphasising. We also organise reactions from the viewpoint of the products, not the reactants. You say that "Elimination of water and elimination of hydrohalide is the same reaction, but since one involves alcohol and the other halogen a student is forced to learn them separately, adding to his burden." but in fact both reactions form alkenes, and so the reactions are also dealt with in the alkene chapter. Similary, it is not exaclty the case that "the conversion of a halide and an alcohol into nitriles become different things" because both reactions come under nitriles too.

Thankyou for highlighting the problem: By organising along the lines of functional groups we have fragmented discussion of reaction types. I think all editors of this book should be conscious of this issue and ensure that common reaction types are cross-referenced as much as possible; and that the appendix on reaction types should be used to draw these common threads together as much as possible.

Ewen 08:54, 31 January 2007 (UTC)

[edit] Content

Re: 59.93.162.4's comments on content:

"Writing a good and original textbook that not simply a conventionally-organised collage from existing textbooks with sudden and inexplicable emphasis on the author's personal interests is a difficult and time-consuming task"

Agreed, and the wiki system is a way to share this task. However, this is an ambitious project and it is a work-in-progress. If some sections are currently further developed than others, and these sections are the result of one or other author's personal enthusiasms and interests, then is that so surprising? Eventually, the gaps will be filled (we hope).

You have identified many areas you consider under-developed. Do please dive in and develop them!

Ewen 08:54, 31 January 2007 (UTC)

[edit] Cost

Re: 59.93.162.4's comments on cost:

The aim of the book is to make it as comprehensive and up-to-date as can be, with constant revisions. The competition would be the books listed on the Main Page, which are more expensive than the wikibook. Of course, you could buy an inferior book or on old copy of a good one; but the quality of this wikibook should justify its limited cost. We're not there yet; but already for the many students who have free internet access through their colleges the cost of this book cannot be beaten.

Ewen 08:54, 31 January 2007 (UTC)

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