Talk:Organic chemistry/Archive 1

Archive 1

Text from September 2001

Shouldn't the information on nomenclature be on a (linked to) separate page, leaving a clearer place to put principles of organic chemistry topics? -- sodium

Vandalism

Without being high brow I think vandalism is not only inserting idiocies but also personal opinion into a scientific article --LouisBB 05:38, 3 August 2006 (UTC)

Article rating

It is a pleasure to write a good article or even to contribute to it editorially, that is, I presume, why we do it. As you begin you are asked to write an article, or to improve a stub, and you achieve 'B' standard from 'stub' standard. Well, it would increase our pride of contributors if we could advance its status a bit further, I presume. I looked at the classification and the criteria, and also the article equivalents in French, German, and Hungarian. None of these language variations even mention classification, never mind actually classifying the relevant articles. So why are we still at class B, and how could we improve our standard. Any ideas ? LouisBB 15:20, 29 June 2006 (UTC)

I have assessed the article's importance as a high importance chemistry article. It could even be 'top' importance since organic chemistry is one of the main divisions within chemistry, though I'm not sure if this qualifies it for such a status. Regarding quality, it had some wording and other small problems that I've cleaned up today, and it needs more references. Addition of a good number of textbooks under something like 'further reading' would be a good start, then citing from such texts and other sources such as scientific journals would improve the article's standing a great deal. It isn't worth nominating for GA yet because of the references, but when it has a few more I would recommend nominating it for good article status. Richard001 02:24, 27 January 2007 (UTC)

Note: Reclassified at top importance as per organic chemistry. Richard001 03:42, 27 January 2007 (UTC)

Phanes

Still trying to solve the problem of the reference to: phanes (organic chemistry) It is a struggle when you are not a very experienced editor, but we'll succeed --LouisBB 11:12, 26 July 2006 (UTC)

General; Definition; Aromatics & polymers

General The whole article needed, and still needs considerable expansion and editing. Characteristics, Molecular structure and Organic reactions titles do not represent their contents properly. Characteristics ought to have divided chemical characteristics and physical properties. I shall have a go at this. Molecular structure: The content of this section is about the characterisation of the compound by (wet or instrumental ?) analysis, not the structure itself. Organic reactions ought to give a few examples of reactions, the reaction formula does not help anybody.

Thanks to DMac for the linking and to those who corrected my inadequate English.

Definition I agree with V8rik; the January definition is better. I don't think that the later definitions were A LOT worse. I'll modify the latest to the following: Organic chemistry is a specific discipline within the subject of chemistry. It is the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or otherwise) of chemical compounds of carbon and hydrogen. They may contain any number of other elements, such as nitrogen, oxygen, halogens, and more rarely phosphorus or sulphur.

Reasons: The subject deals with preparation of compounds in general, not only synthesis Other authors call organic chemistry Carbon chemistry, but hydrogen also needs a mention Mentioning organic in the definition sounds a bit like defining something by itself

Aromatics & Polymers sub-section These sub-sections were added relatively recently as previous versions for Classifications seemed grossly inadequate. It may still is. The author of the comment may make his own contribution. Chemical bonding theory could still be expanded in the sub-section on Chemical caracteristics to be proposed later LouisBB

organic compound

I'm not ready officially to propose a merger, but could organic compound be merged with this article? Olin 21:55, 10 February 2006 (UTC)

Although there is some obvious overlap between the two articles, I think there are enough differences so that each warrants a separate article. Edgar181 15:54, 14 February 2006 (UTC)

Considering that an organic compound is a noun in the sense of being a 'physical' object, whereas organic chemistry is a concept or subject, they don't seem to be possible for merging. I can understand what organic chemistry is, but I may want specifics on organic compounds. Better to leave them divided rather than clutter this page up.--OMG LAZERS 13:57, 24 April 2006 (UTC)

definition of organic chemistry

Why don't we say that the subject of chemistry has two main divisions: 'inorganic chemistry' which deals with the elements and naturally occurring chemical compounds, and 'organic chemistry' which deals with the rest ?

From the introduction the reader does not realise the fact that the 'organic' name has become a misnomer, and how it has become such. (A hypertext reference to carbon is not enough). How the name 'organic compound' has originated from the fact that these compounds are important constituents of living, or once living organisms, and that they were found always to contain carbon, and that the 'organic' context has now been superseeded in reality by the fact that carbon compounds found in organisms and compounds like them can be and are being artificially manufactured. Thus: organic chemistry could be justifiably called 'carbon chemistry' because the number of carbon compounds that 'inorganic chemistry' could justifiably deal with is a negligible proportion of the totality. LouisBB 07:40, 14 April 2006

• I disagree with this classification on basis of factual correctness. Chemistry is not divided this way! Organic chemistry has a very specific chemical meaning: the study and synthesis of compounds formally derived from methane (this is to exclude compounds like carbon dioxide and graphite, which are not considered to be organic). Inorganic chemistry deals with the study and synthesis of the remaining compounds (e.g. metals, ionic salts, non-carbonaceous coordination complexes, et cetera). However, there are yet other branches of chemistry: physical chemistry concerns itself with the study of fundamental processes that occur in atoms and molecules (e.g. bonding, vibrational modes, thermodynamics, et cetera); organometallic chemistry is a strange hybrid of organic and inorganic and is often related to modern catalysis; biochemistry looks at organic and organometallic chemistry (often involving proteins) in living systems; supramolecular chemistry tries to scale organic and inorganic chemistry beyond the small molecule world to large, geometrically ordered complexes. Shultzc 06:08, 13 October 2006 (UTC)

I feel, that a slight re-write is needed in para 2. The fact that inorganic substances are found in organic substances does not contradict the original proposition, as the ancient belief did not state that organic substances could not coexist with inorganic ones. so the second phrase is not a logical contradiction, it ought to be stated separately. What contradicts the ancient belief is what is described later in the History section (eg by Chevreuil and Wőhler)

LouisBB 14:35, 29 January 2007 (UTC)

Reactions

My goal is to eventualy organize them by type (i.e.: amine, benzene, alkyl, etc...). Does anyone think it might be better to move them to their own page, as this list can get extensive?

It would be nice if you could flesh them out or reorganize things. As it is right now, it's sort of an indiscriminate collection of information. Isopropyl 02:44, 18 April 2006 (UTC)

The Organic reaction page, linked from the beginning of the "Organic Reactions" section that you edited, already has a good start, including links to the many existing relevant subpages. DMacks 02:48, 18 April 2006 (UTC)

I see. I didn't notice the link. I'll remove my list and work on that page. Also sorry about the indiscriminate collection of information, I did plan on working on it to make it more informative over time. Thanks for the page, though. I'm new and need to start reading more of the guidlines now that I want to post. jimktrains 12:51am 18 Apr 2006 (EST)

Naming of organic compounds

What is the correct and most common method (or most modern) for naming organic compounds? I have been taught to name the chemicals in the table below as follows (see bold names). What naming method is most commonly used in the real world?

Family name	Functional group	Example		Note No
Alcohol	-OH	Methanol	CH3OH
Aldehyde	-(H)O	Methanal	HCH(O)	1.
Ketone	=O	Propan-2-one	CH3-C(O)-CH3
Ether	-O-	Methoxymethane	CH3-O-CH3
Amines	=N-,or =NH,or –NH2	Dimethylamine	CH3-NH-CH3
Carboxylic acid	-C(O)OH	Methanoic acid	H-C(O)OH	2.
Ester	-C(O)O-	Methyl methanoate	H-C(O)O-CH3

The real question is do you want to be IUPAC-compliant or do you just want to communicate, and if the latter, what's the audience? Yours are correct by IUPAC, but they are fairly rare in modern literature (especially in the US) and most other situations where the goal is "communication" not "pedantic correctness". Maybe pay a visit to Organic nomenclature. DMacks 20:03, 5 May 2006 (UTC)

• Do we really need this table? Keeping this table up to date seems to me mission impossible IV The complete table is already maintained in functional group V8rik 23:18, 6 May 2006 (UTC)

Such a table is necessary to give at least a sample of names to the reader. Rather than removing, it ought to have been extended. I shall not attempt to re-instate it for the present till the associated wordings can be improved upon. Moreover a list of common 'readicals' used in naming ought also to be included.

However I am including a new section instead of the preamble to Classification, because it is important to be able to define the compounds before one tries to classify them. See latest edition. If hypertext liens are not extensively used it is because it is difficult to know what 'real' references exist (comment to DMacks remarks)

Do we want IUPAC compliant or just to communicate? The IUPAC naming recommendations are supposed to aid the workers and students of organic chemistry, so their mention cannot be omitted, but we ought to state also that in practice for many compounds their common names are used for convenience. LouisBB 22:03, 18 May 2006 (CET)

What I know from IUPAC they encourage you to use acetic or formic acid instead of Ethanoic and Methanoic acid. If this is correct the non systematic names should also be in! But if this table already exists in an other page, the work to maintaine both is not neccesary.--Stone 08:57, 19 May 2006 (UTC)

• A brief note has been added to this sub-section to highlight the fact that the IUPAC names serve as guide and recommendations and not as a dogma LouisBB 17:50, 22 May 2006 (CET)

opening sentence not an improvement

Currently a lot of work done on the opening line but the quality deteriorates. The text even contains redlinks. There was nothing wrong in my mind with the opening line of lets say 2 months ago:

Organic chemistry is the scientific study of the structure, properties, composition, reactions, and synthesis of organic compounds that by definition contain carbon. It is a specific discipline within the subject of chemistry. Organic compounds are molecules composed of carbon and hydrogen, and may contain any number of other elements. Many organic compounds contain nitrogen, oxygen, halogens, and more rarely phosphorus or sulphur. V8rik 23:02, 6 May 2006 (UTC)

• restated definition that already existed in this version of january 2006 V8rik 21:53, 13 May 2006 (UTC)

The above text was better than the current one, but in the light of the peer review (and the remark here, below for cleanup) I would like to propose the following modif to the opening sentence to make it less frightening but the bracketed remark could be removed:

Organic chemistry is that part of chemistry, which deals (neglecting a few exceptions) with the chemical compounds consisting primarily of carbon and hydrogen. They may contain many other elements, such as nitrogen, oxygen, halogens phosphorus, silicon sulfur and others. The scientific discipline involves the study of their structure, properties, composition, reactions, and preparation (by synthesis or by other means)

LouisBB 04:31, 31 March 2007 (UTC)

Alteration of Aromatic and Polymers sections

These two sections need extensive revision and are factually incorrect. For example, the word hydroaromatic is made up, there is no mention of the chair confomration in cyclohexanes, no mention of the rules of aromaticity i.e. cyclic, conjugated, planar, 4n + 2 pi electrons, the random placing of the words "radical" and "monomer" in the polymer section to render the first sentence inconprehensible!

Note polymers can be constructed by radical and condensation reactions and the term monomer is defined as sub unit that the polymer is derived from.

• The rarely used term of hydroaromatics has been replaced by the IUPAC alicyclics term. Cyclopropane, cyclopentane, and cyclohexane are commonly used terms. Aromaticity is not an organochemical term. The polymer section is yet to be edited. LouisBB 11:35, 24 May 2006

• It is a pity that the writer of the unsigned comment did not volunteer to put something better forward.

Re-thinking the polymer section: It does seem to me that the 'radical' name is not appropriate as the definition of radical is an atomic group (sometimes?) electrostatically charged (extra or missing electron or electrons) that pass from one molecule into another without change. However the Note attached to the unsigned comment asserts that polymers can be made by 'radical reaction' so perhaps I am wrong, in which case what is the matter with the original statement?

However, I shall re-write the first sentence trying to make it more concise.

Referring to the other polymerisation reaction mentioned there 'condensation': to my understanding this is inappropriate as the definition of 'condensation' is an organochemical reaction in which two (or more?) chemical units combine whilst they release a secondary product of small molecular weight, such as water, or ammonia etc.

No comment about the semantic argument over the 'sub-unit' term.

Does anybody else have other thoughts?

LouisBB 08:40, 9 June 2006 (UTC)

Having looked at the text under the various polymers I now realise the complexity of the subjest and the need for expansion of this section. The terms 'radical polymerisation' and 'condensation polymerisation' do exist, this latter being polymerisation in the presence of condensation. These terms with several other, such as 'cationic', 'anionic', 'ion-co-ordination', and the term 'tacticity' are to be incorporated.

LouisBB 10:27, 9 June 2006 (UTC)

• This page (being a portal) should present a broad overview of organic chemistry without much details. Expanding this article with regard to polymer is therefore unwarranted, extensive articles exist for such topic as tacticity, Cyclohexane conformation and polymerization exist and should only be briefly mentioned. Lets try to cover the basics on this page and the details on their respective pages. V8rik 15:52, 9 June 2006 (UTC)

I agree with V8rik here...discussion of the intimate details of different types of polymerization reactions and polymers doens't belong here. There's a reason we have Polymer and Polymerization pages and even pages for certain types of polymerization reactions, though those could use some diagrams and better explanations. Even the sentence about the dimer/trimer terminology might be too much detail for here. And after we say what a homopolymer is, the complex description:

When it was found that physical characteristics such as hardness, density, mechanical strength, abrasion resistance etc could be changed to advantage by the addition of a secondary monomer to the polymerising mixture a new type of polymer was born called a heteropolymer. The secondary, (property-modifying) monomer added in smaller proportions to the first to make the polymer is sometimes called a co-polymer.

(which isn't specific to heteropolymers, but sounds like it is) could be simplified to:

If more than one type of monomer unit is used in a chain, it is called a heteropolymer or co-polymer.

and then simply state:

The specific monomer(s) chosen, the chain length and amount of chain branching, and the ratio and clustering of various different monomers (if a heteropolymer) affects all properties of the resulting material, including hardness, density, strength, and abrasion resistance.

DMacks 16:28, 9 June 2006 (UTC)

• Thanks for the comments, one learns this job as one goes along. Ok.

Prior to changing the text I offer the following new text to go after the examples and to replace the text of paragraph 1 after "When" etc as DMacks suggest, omitting the reference to dimers:

The examples are generic terms, and many varieties of each of these exist, with their physical characteristics fine tuned for specific use. Changing the conditions of polymerisation changes the chemical composition of the product by altering chain length, or branching, or the directional arrangement of asymmetrical units. Further, secondary component(s) may be added to create a hetero-polymer (co-polymer) and the degree of clustering of the different components can also be controlled. Physical characteristics, such as hardness, density, mechanical or tensile strength, abrasion resistance, heat resistance, transparence, colour, etc. will depend on the final composition.

LouisBB 04:15, 15 June 2006 (UTC)

• Thanks again for the comments. A new text has been prepared for these two sections trying to make them more concise and perhaps more portal-like. An expert volunteer is required to write an article on disambiguation of phanes to get rid of the organic phanes reference.

LouisBB 04:52, 21 June 2006 (UTC)

• I have largely rewritten the section on cyclic compounds. Does it now appear better to everyone? Shultzc 19:43, 12 October 2006 (UTC)

Functional groups

Re-thinking the present text and organisation of Classification it seems to me that a separate section should be added with a list (as full as we can make it) of the categories characterised by the functional groups. I intend to remove the 'Functional groups' from the 'Aliphatics' section to create a new section as below. The appropriate list as table or otherwise would follow I intend to do this, say, at mid-June, having listened to colleague-editors comments.

TEXT PROPOSED

Functional groups

Certain atomic configurations within organic molecules have decisive influence on the chemical and sometimes physical characteristics of the compound and thus those containing the same atomic formations have similar characteristics, which may be miscibility with water, pH , chemical reactivity, oxidation resistance, or others. Such configurations have been named functional groups

Apart from the groups some elements, such as O, N, or Cl bond within the organic molecules similairly to the functional groups and their bonding is quite characteristic to the individual elements concerned. These though their name is not strictly appriopriate, can be classed with the functional groups. In chemistry, structure is quite synonymous with function, and so the structural categories double as categories of property or activity.

Because each functional group has its own specific effect on the molecules in which it is present they lends excellent means for characterisation and classification.

Some functional groups are also radicals , similar to those in inorganic chemistry, defined as atomic configurations which pass from one chemical compound into another during chemical reactions without change

Many, if not all of the functional groups which are typically present with aliphatic compounds are also represented within the aromatic and alicyclic group of compounds, unless they are dehydrated, which would lead to non-reacting co-optional groups.

Important functional group based categories are listed below

LouisBB

Spelling

What are the guidelines for the English Wikipedia? Is the spelling supposed to be English (UK) or English (US)? Sulfur (US) is sulphur in the UK. Searching the Oxford English dictionary has 20 entries in it as sulphur, only 2 as sulfur? Valency (UK) against valence (US) is only 6 to 2. So are we striving for cosistency, and if so why?--LouisBB 21:20, 29 July 2006 (UTC) (moved to bottom of page by Dirk Beetstra ^{T C} 21:39, 29 July 2006 (UTC))

The spelling used is the spelling used by the first editor of an article (i.e, if the original article is written in UK-EN, then that should be continued). For pages like sulphur and aluminium things are a bit different, there the name is used that is given to the compound by IUPAC. Other pages are a redirect to that page. --Dirk Beetstra ^{T C} 21:39, 29 July 2006 (UTC)

• The spelling should be US (more users). Wiki should also consider expanding their application automatically converting UK to VS and vice versa based on user preferences. V8rik 22:28, 29 July 2006 (UTC)

jchem.info removed due to copyright

Dear Sirs, I have removed the link to jchem.info because

• [1] is copied from [2]
• [3] copied from [4]
• [5] copied from [6]
• [7] copied from [8]

Jchem.info has erased any copyright remark that points to organic-chemistry.org —The preceding unsigned comment was added by 213.188.227.119 (talk • contribs).

If we are all convinced that this NAMELESS user is bona fide, then it's OK by me, but are we certain? Something important might be wiped for no good reason. If you repeat something already repeated that cannot be copyright. LouisBB 14:36, 29 March 2007 (UTC)

"Description and nomenclature" cleanup

I added a cleanup tag to the "Description and nomenclature" section, becausde certain sentances were merely fragments I don't feel I personally have the knowledge to merge together appropriately. — Lenoxus 20:55, 14 January 2007 (UTC)

I sort of take it back: There were really only a couple offending words (now changed) which had thrown the whole thing off for me. So yeah, never mind. That said, if anyone readily familiar with the topic would like to chop up some of the sentences, that would be great to help us newcomers follow along -- right now, there's a lot of clauses in a given sentence. At present, though, they don't actually violate any grammatical rules. --Lenoxus 21:56, 17 January 2007 (UTC)

Ref: to do, and where to get help

From what I've seen of it the Organic Chemistry book of Wikimedia is superbly structured by a number of eminences. Does anyone know if we can (and if not, then why not) rely on 1) its structure, 2) its links, 3) its illustrations 4) its citations etc to improve our (presumably) simplified and shortened version  ? For those (of us) who do not have good library access there are no better citations than those (indirectly) in an on-line book.

Is the Inorganic chemistry article a good example for us to imitate? In a conventional encyclopedia there are much fewer illustrations under to the same title (perhaps only one in general ?) So ought the titles be broken up there, or is Wikipedia supposed to be different ? Questions to contemplate --LouisBB 18:37, 3 February 2007 (UTC)

It should be the other way round:

• Wikibooks hardly contains internal linking which in my view is key in wikipedia. Without internal linking many of the chemistry texts are just technical jargon.
• I hardly see images that can be of use in wikipedia. Many pages in wikibooks are copies of wikipedia see for instance the article on amines
• Wikibooks does not really bother with references, I hardly see them.

I have remarked in the past that the resources in manpower that we have are too thinned out over many many different projects, wikibooks one of them

V8rik 22:08, 3 February 2007 (UTC)

Looking at the peer review

Since I looked at this article last it has much improved, mainly the first part, but I think that the introductory sentence would be clearer broken into two.

1) Heeding the peer reviewer I agree, that there are several brief statements made here and there without explanation or even a link

Historic highlights last para last sentence promising = promising what?

Historic highlights penultimate para too hard to follow

Hydrocarbons and functional groups third para after ...unless etc = explain?/reference?/wipe?

2) Characteristics section still needs reorganising:

Because both characteristics and organic reactions depend on the same factors (molecular structure/atomic structure which are factors thoroughly discussed in other works on Organic chemistry but not YET by us) I would group them one after the other

I would break up Characteristics to Chemical, and Physical, and detail under characteristics why and how atomic and molecular structure influences them

I would explain as explained by Richard and Sally Daley (Ref 2.)why we pick on those few physical characteristics that we discuss here: because they give us clues on determining what compound we are looking at in the lab.

I think it is important to at least mention the effect of the prevailing conditions on both the physical and chemical characteristics: We do not mention anywhere for instance that organic compounds, like inorganic ones are found in three states of aggregation (forgetting about the fourth)

3) Organic reactions

We ought to mention I) the main reaction types of the organo-chemical reactions and II) define the Named reactions and say where we can find a list for them

All this is rather a lot still to make it really VG - I think. I shall do something in my sandbox User:LouisBB/OrgChem, because it would be too much here. Feel free to criticise.

I admit, I am poor on references, but in a small village I have no library access. LouisBB 15:33, 29 March 2007 (UTC)

Vitalism and Wöhler

I don't feel that the change to include 'attack' was appropriate. Attack implies a conscious and deliberate effort, wheras someone even commented that Wöhler's action was nothing like that. LouisBB 14:18, 31 March 2007 (UTC)

Appropriate External Links

Why were the Claude Wintner Organic Chem lectures deemed inappropriate external links?

Restored, though I have doubts about the length of the external links. See here. --Rifleman 82 19:18, 9 April 2007 (UTC)

Orgo

Does anyone know why Organic Chem is called "orgo?" We are just curious. Thanks. Fbertram 16:11, 23 May 2007 (UTC)

Just a convenient short-form I guess. Gotta be something distinct ("organ" is already taken), like how there's no short-form INN name for the interferons because the obvious stems all have other meanings. I always wondered why they call us "organikers". DMacks 16:17, 23 May 2007 (UTC)

I think a lot of this comes out of undergrads. It is a Freshman that asked the question about orgo. I am actually an Analytical guy, but have always done Organic Analytical work, and some synthesis. The term "organiker" was in use in 1964 when I was taking "Orgo." It was intended to be a derogatory term, used by Chem majors who hated Organic. On the other side of the coin, The Organic people at that time kind of sneered at Analytical people, because they felt we were less than worthy. That came from the fact that most of the early analytical techniques were developed by Organic people, and had been used by them for years. Obviously, the discipline of Analytical has grown and bloomed, and I hope that such animosity no longer exists anywhere within Chemistry. I have been out of the academic scene for a number of years now, so I don't know. Thanks for your reply.Fbertram 14:36, 29 May 2007 (UTC)

Ah well this rivalry will never end. Where I am, we synthetic chemists think analytical chemists, surface scientists, catalysis guys and other applied chemists as somewhat deficient as chemists. And among the synthetic chemists, we organometallic chemists believe we can do organic reactions as well as organic chemists can, while they know nuts about inorganic chemistry. --Rifleman 82 14:48, 29 May 2007 (UTC)

Thanks for your perspective Rifleman. I have found that it comes down to whatever the job requires. If you are going to keep your job, you learn fast. I worked as an engineer for a few years, and even became pres of the local EE society. Was glad to get back in Chem, though. BTW, I see you were in the Singapore military. Congrats on that. I take it that's where the screen name comes from. I was an expert marksman in the US Army. Gotta get back to the lab. Later.

organic chemistry is absolutely the most positively gargantuant subject in the human organism —Preceding unsigned comment added by 216.229.196.25 (talk) 16:31, 23 April 2008 (UTC)

History

Shouldn't history be one of the first sections? Mathew551 (talk) 15:35, 15 November 2009 (UTC)

I moved it to the end, thinking that most readers would want to know what is organic chemistry, not where it came from. But you can certainly move it to where you think it should be, that's the nature of this project.--Smokefoot (talk) 15:57, 15 November 2009 (UTC)