Talk:Diels–Alder reaction

I think that it is time to remove the {{complex}} template. Does anyone object? Racepacket (talk) 04:47, 29 July 2011 (UTC)

Too soon. Have a look at the data and the comments below:

• Indication of the number of years of formal education that a person requires in order to easily understand the text on the first reading
  • Gunning Fog index : 12.70

• Approximate representation of the U.S. grade level needed to comprehend the text :
  • Coleman Liau index : 19.92
  • Flesch Kincaid Grade level : 11.41
  • ARI (Automated Readability Index) : 14.36
  • SMOG : 11.06
  • Flesch Reading Ease : 29.79

Now these numbers are only indicators. For example it could be possible to write complete gibberish that met word and sentence length, syllable counts etc. And also, complex science articles (or anything with technical jargon) is going to be hard to simplify beyond a certain point without losing accurate meaning. It may also be reasonable to argue about "who" is the audience for an article on advanced chemistry topics.

However, I would like to see much better figures (eg Flesch Reading Ease of at least 50, and ideally 60-70). I would also like to be able to read the article myself (uni educated but with no background in chemistry) and have a basic idea of what the article is about. One problem for me is linking complex terms to another complex article. That is I follow the link and I am still no better off. You (Racepacket) have said that you want a simple lead/opening paragraph, and with complexity in article proper. This could be a good start.

The first link takes a couple of clicks to find out what a chemical reaction is, and then more to go backwards and forwards to track down what it means in terms of organic compounds. Whatever a compound is. Then there is info about a "new ring" (?) and a "double bond" (?). Then there is more links to complex pages, and a then info about "decomposition of a cyclic system". Now I can get the part about the process (whatever it is) working in reverse. In the next paragraph it mentions that this is the "Mona Lisa" reaction. Why? Is it about something unknown, is it valuable, did da Vinci have a part in it, does it have an enigmatic smile?

If writing for Simple Wikipedia was easy, then anyone can could it, but this is no easy task. If you are up to the challenge then I am happy to give you my full support. Organic chemistry is not a topic we have many articles about, and will enjoy reading them. A little bit of advice: often when doing a "cut and paste and simplify" method from ENWP, it is really hard to get down to basics. I have often have to go back and actually write the article from scratch. Secondly, where there are lots of technical terms, then it becomes really important that everything else is made as simple as possible. I am happy to help you get an article (this one?) into a great simple English article that we can both be proud of. I don't know much about chemistry (well nothing actually) but I do have a lot of experience writing in Simple English. --Peterdownunder (talk) 12:31, 29 July 2011 (UTC)

Thank you for your thoughtful response. I am a bit skeptic about the numeric index approach because a number of them use word-length as a criteria. By definition, most chemical terms of art are poly-syllable words. Also, just as mathematicans talk in equations, we talk with diagrams. Those don't factor into the readability index scores.

Just as any history of art encyclopedia must include covering the Mona Lisa, the Diels-Alder reaction is so fascinating to chemists that it is a must for Simple English wiki as well.

It will probably take adding at least a dozen more linked-to articles before this article becomes accessible to the novice reader. This is a "chicken and egg" problem. Thanks, Racepacket (talk) 18:32, 29 July 2011 (UTC)

Numerical Approach

I understand your concerns about a numerical approach, so I tried a little experiment. I took a few sentences that I thought were complex and substituted "dog", "table", and "book" for some of the chemical terms, like this:

• Before

Though common, this feature is not exclusive of Diels–Alder dienophiles.

The dienophile undergoes Diels–Alder reaction with a diene introducing such a functionality onto the product molecule. A series of reactions then follow to transform the functionality into a desirable group.

To determine which is the endo and which is the exo transition state, the two molecules are oriented parallel to each other, so that diene's single bond (one which connects two double bonds) is parallel to dienophile's double or triple bond.

• After

Though common, this feature is not exclusive of Diels–Alder dogs.

The dog undergoes Diels–Alder reaction with a dog introducing such a functionality onto the product molecule. A series of reactions then follow to transform the functionality into a desirable group.

To determine which is the table and which is the book transition state, the two molecules are oriented parallel to each other, so that dog's single bond (one which connects two double bonds) is parallel to dog's double or triple bond.

I used EditCentral to check them and got these results.

• Flesch reading ease score: 59.9
• Automated readability index: 12.3
• Flesch-Kincaid grade level: 9.9
• Coleman-Liau index: 12.2
• Gunning fog index: 15
• SMOG index: 13.2

Yes, I did pick some sentences that I thought were complex. Parts of the article are getting simpler. But, I think this shows that it isn't just the chemistry terms, it is also the sentence structure. Avoid passives. Try to use direct subject-verb-object sentences without introductory phrases or clauses. Anything with a semi-colon in it is probably not simple. I hope those kind of specifics help. Gotanda (talk) 23:07, 29 July 2011 (UTC)

I take your "experiment" in the constructive spirit that it was offered. I agree with the semi-colon, appositive, dependent clause advice. However, I think your experiment was flawed. Look at:

Though common, this feature is not exclusive of beans dogs.

The dog undergoes beans with a dog introducing such a functionality onto the beans. A series of reactions then follow to transform the functionality into a bean.

To determine which is the table and which is the book bag, the two beans are oriented parallel to each other, so that dog's bone (one which connects two bones) is parallel to dog's beans.

• Flesch reading ease score: low 73.4 (above goal of 65)
• Automated readability index: low 9
• Flesch-Kincaid grade level: low 7.5
• Coleman-Liau index: medium 9.3
• Gunning fog index: medium 11.6
• SMOG index: medium 10.7

A chemistry reader seeks bigger conceptual/jargon "chunks" than Gotanda spotted in his experiment. I need more skill in drafting "compare and contrast" reasoning in terms of simple English. Thanks, Racepacket (talk) 00:42, 30 July 2011 (UTC)

This is such a challenge that I cannot resist it. I have started trying to simplify this page in my sandbox. Please feel free to check it out and see if I have it right. At the moment I am just looking at the opening paragraphs. --Peterdownunder (talk) 01:54, 30 July 2011 (UTC)

Opening paragraphs redone, the Flesch Reading Ease score for the opening is 63. --Peterdownunder (talk) 08:16, 30 July 2011 (UTC)

Numeric penalty for spelling things out in simple terms

One way to make an article simple is to state an idea both in techincal and also in simple terms. The numeric scores appear to penalize such explications. I have taken some phrases for English Wikipedia and my simplified translations of the same passages. English wikipedia:

The McLafferty rearrangement is a reaction observed in mass spectrometry. It is sometimes found that a molecule containing a keto-group undergoes β-cleavage, with the gain of the γ-hydrogen atom. This rearrangement may take place by a radical or ionic mechanism.

These reactions are usually unnamed, being categorized by the following criteria:

electrocyclic reactions are photoinduced or thermal the number of pi electrons in the species with more pi bonds determines reaction mode electrocyclic reaction can be a ring closure (electrocyclization‎) or a ring opening reaction the stereospecifity is determined by conrotatory or disrotatory mode of transition state formation as predicted by the Woodward-Hoffmann rules.

For the 5,6-dimethylcyclohexa-1,3-diene, only a disrotatory mode would result in p-orbitals having the same symmetry as the HOMO of hexatriene. For the 3,4-dimethylcyclobutene, on the other hand, only a conrotatory mode would result in p-orbitals having the same symmetry as the HOMO of butadiene.

• Flesch reading ease score: very high 25.7
• Automated readability index: very high 17.7
• Flesch-Kincaid grade level: high 15.8
• Coleman-Liau index: high 16.5
• Gunning fog index: very high 20.1
• SMOG index: high 16.8
• 1037 characters

Simple English:

The McLafferty rearrangement is a reaction observed in mass spectrometry. When a molecule is analyzed by a mass spectrometer, it breaks apart in consistent ways that chemists can predict. The McLafferty rearrangement happens in an organic molecule containing a keto-group. The keto-group undergoes β-cleavage, with the gain of the γ-hydrogen atom. This rearrangement may take place by a radical or ionic mechanism.

Electrocyclic reactions have the following in common:

electrocyclic reactions are driven by light (photoinduced) or heat (thermal) the reaction mode is determined by the the number of pi electrons in the part with more pi bonds an electrocyclic reaction can close a ring (electrocyclization‎) or open a ring the stereospecifity is determined by conrotatory or disrotatory mode of transition state formation as predicted by the Woodward–Hoffmann rules.

The above diagram shows two examples. For the 5,6-dimethylcyclohexa-1,3-diene (top row of diagram), only a disrotatory mode would result in p-orbitals having the same symmetry as the HOMO of hexatriene. The two p-orbitals rotate in opposite directions. For the 3,4-dimethylcyclobutene (bottom row of diagram), only a conrotatory mode would result in p-orbitals having the same symmetry as the HOMO of butadiene. The p-oribtals rotate in the same direction.

• Flesch reading ease score: high 39.2
• Automated readability index: high 13.4
• Flesch-Kincaid grade level: medium 12.2
• Coleman-Liau index: high 14.9
• Gunning fog index: high 16.9
• SMOG index: high 14.4
• 1342 characters

Simpler english

When you need to explain the jargon, it will take longer. In this case simpler may not mean shorter:

The McLafferty rearrangement is a chemical reaction that can be studied by using mass spectrometry. When a molecule is studied by a mass spectrometer, it breaks up in consistent ways. Because of this chemists are able to predict what those changes will be. The McLafferty rearrangement takes place in organic molecules which have a keto-group. The keto-group goes through a process called β-cleavage. During this process it gains the γ-hydrogen atom. This rearrangement can take place by a radical or ionic process. Electrocyclic reactions have the following features in common:

• they are powered by light (photoinduced) or heat (thermal)
• the type of reaction is decided by the the number of pi electrons in the part with more pi bonds
• the reaction can close a ring. This is called electrocyclization‎
• the reaction can open a ring
• the stereospecifity is decided by the way the pi electrons rotate as they open or close the ring. This can be predicted by using the Woodward-Hoffman rules. If they rotate the same way it is called conrotatory. If they rotate in opposites ways it is called disrotatory.

The above diagram shows two examples. For the 5,6-dimethylcyclohexa-1,3-diene (top row of diagram), only a disrotatory change would give the p-orbitals the same symmetry as the HOMO of hexatriene. The two p-orbitals rotate in opposite directions. For the 3,4-dimethylcyclobutene (bottom row of diagram), only a conrotatory change would give p-orbitals the same symmetry as the HOMO of butadiene. The p-orbitals rotate in the same direction.

From Edit Central:

• Flesch reading ease score:medium 61.2
• Automated readability index:medium 9.5
• Flesch-Kincaid grade level:low 8.3
• Coleman-Liau index:medium 11.7
• Gunning fog index:medium 12.6
• SMOG index:medium 11.6
• 1543 characters

There are several parts of the above passage that would need more explanation such as: radical, β-cleavage, γ-hydrogen and the chemical susbstance names used like 5,6-dimethylcyclohexa-1,3-diene and hexatriene for example.

It will not be easy, but I think it can be done.--Peterdownunder (talk) 23:24, 30 July 2011 (UTC)

My point was that I took passages from several articles where I added the extra explanations and compared them to the original English Wikipedia passages. The act of adding the explanation made the passages score as "less readable." That does not mean that the explanation should not be added. Rather it means that the scores are not a good measure of our success. Racepacket (talk) 15:36, 1 August 2011 (UTC)

Flesch

The routine you are using for readability is giving you incorrect scores. Use this one:

• Readability [1]

You will see that the passage is still far too difficult. Macdonald-ross (talk) 06:14, 1 August 2011 (UTC)