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Talk:Friedel–Crafts reaction

Mechanism
This article could perhaps do with a more thorough mechanism, explaining the action of the AlCl3? Sorry I can't do this myself, but my TeX skills are sorely lacking -- Tom

— Preceding unsigned comment added by 81.178.141.153 (talk) 20:29, 12 June 2005 (UTC)

Problem with methyl example
One of the reactions shown is the addition of a methyl group to a benzene. The mechanism for this addition involves the loss of the halogen from the alkyl halide and the formation of a carbocation. The methyl carbocation is far too unstable to allow for the addition of a methyl substituent to benzene through the Friedel-Crafts reaction. Furthermore, the reaction would not occur with even a primary alkyl halide (such as the addition of an ethyl group, as shown later in the article) as primary carbocations are also much too unstable to allow for addition. --Ian

— Preceding unsigned comment added by Asian Fury (talk • contribs) 06:01, 5 December 2005 (UTC)

Stability of carbocations
No, methyl groups and primary alkyl halides CAN react in Friedel-Crafts alkylation. In the case of secondary and tertiary halides, the carboation is formed by the removal of the halogen ion by the Lewis Acid. However, because methyl and primary carbocations are NOT stable as you stated, the halide instead forms a Lewis acid-base complex with the acid, and this acts as the electrophile in this case: CH3CH2-Cl + AlCl3 -> CH3CH2-Cl(+)-Al(-)-Cl3. I'll add this later to the main article, with some fancy drawings. Jhum101 18:40, 23 February 2006 (UTC)

Wrong molecule used for reference
The article references making 2,4,6-triethylbenzene. However, not only is this wrongly named, it does not form as such. The foot-note lists an abstract for 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene, but this is a different molecule, and the abstract doesn't even mention friedel-crafts. I'll fix this later, and add a new section on the limitations of friedel crafts reactions (specifically, polyalkylation, reactivity, and the para/ortho substitution.) Jhum101 18:40, 23 February 2006 (UTC)

Hi Jhum101, I agree that 2,4,6-triethylbenzene should be 1,3,5-triethylbenzene. This compound is the first reaction step in the eventual synthesis of 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene (consult the complete article if you want to check this information). Also even though the article does not specify a friedel-craft, it can be deduced from the reaction conditions that it is one. V8rik 19:35, 23 February 2006 (UTC)

Hmm, I just looked over the article, but my problem with this section is that this is an exception to the normal rules about activating groups and ortho/para directors vs. deactivating groups and meta directors. This is a special case, and when most Friedel-Crafts reactions take place, the alkylated product further activates the ring, and promotes additional substitution in the ortho and para positions. The reaction in the reference has nothing to do with this activation, instead, relying on overall steric hinderance. It is possible, but in the grand scheme of the Friedel-Crafts reaction, the majority of product which undergoes polyalkylation does so in the ortho and para positions. Thermodynamics and stability are important concepts when considering the reaction, but in this case, the Hammond Postulate is applied, and the stability of the intermediates determines the product results. Sorry for the lengthy note, but this could be a confusing article for someone unfamilar with the topic, and this discussion may just overcomplicate the subject. Jhum101 04:23, 24 February 2006 (UTC)   (also, I plan to update the main page with info on substituents, a detailed look at the mechanism and carbocations, other functional groups that can be used to form the carbocation (alkenes and alcohols), intramolecular Friedel-Crafts rxns, limitations with substituants, and polyalkylation. It's a lot of work, and right now, I have more pressing O-Chem labs to finish.)

Hi Jhum101, The best way to go forward I guess is to add content on general FC reactions. I am looking forward to read your contribution. My contribution does not involve an exception though, it is about reversible FC and associated with it thermodynamic reaction control. Also, Wiki readers are intelligent readers, we just have to make sure that basic topics are well separated from advanced topics in order not to get the reader confused. V8rik 23:46, 25 February 2006 (UTC)

Prehapts a seperate section on themodynamics and stability of products? This could be seperate from the general kinetics of Friedel-crafts reactions. Jhum101 02:25, 27 February 2006 (UTC)

 * sounds like a plan, happy editing! V8rik 23:35, 27 February 2006 (UTC)

 * Actually, for successive alkylations on a benzene ring, steric control is more the rule than the exception. Ortho para direction is only true for electrophilic aromatic substitution reactions that are essentially irreversible. Alsosaid1987 (talk) 14:56, 29 August 2018 (UTC)

Stability of electrophile in FC acylation
The reason for lack of rearrangement of the carbocation electrophile in FC Acylation is "there are no carbocation rearrangements as an aromatic carbocation is very stable compared to alkyl carbocations." This is just wrong - the carbocation isn't aromatic. The reason is the resonance stabilisation where the empty shell of the Carbon interacts with the lone pairs of electrons on the oxygen in the acyl group. This should be changed, no? --DapBot 00:32, 15 June 2006 (UTC)

Errors in alkylation mechanism
According to the mechanism, you start and end with the same compound (benzene) and lose the R group somewhere along the way. Also, as mentioned previously the mechanism does not directly involve an alkyl carbocation as an intermediate. It would be good if someone could edit the mechanism to rectify these things.--Joe

— Preceding unsigned comment added by Jtfletcher (talk • contribs) 22:37, 10 April 2007 (UTC)

Does anyone have a acylation mechanism?
anyone?

I could easily make a general acylation mechanism using software on my own computer however bringing the necessary files into the article is assuredly not my area of expertise — Preceding unsigned comment added by Isntitbull (talk • contribs) 02:45, 10 April 2012 (UTC)

Reaction conditions
The article mentioned 'Reaction conditions are similar to the Friedel-Crafts alkylation mentioned above' in the Friedel-Crafts acylation section.

Many different sources give different conditions for this reaction, and I'm interested to know why, and what are the true conditions.

Crazyjoe 7 12:32, 24 June 2007 (UTC)

Chemistry is an experimental science and there seldom are "true" conditions apart from some prerequisites. For example, the Friedel Crafts reaction will definitely need a Lewis acid catalyst (e.g. FeCl3, AlCl3, etc), and to prevent hydrolysis of the catalyst, anhydrous conditions are desirable. Different temperatures and pressures and catalyst loadings will probably work, though they may affect yield and reaction time. This is representative of synthetic chemistry. --Rifleman 82 13:49, 24 June 2007 (UTC)

Error in Friedel-Crafts dealkylation section
The image and description of the Friedel-Crafts dealkylation reaction portray an alkylation, not a dealkylation.
 * Incorrect: the text with the image clearly states that the product forms by a series of alkylations and dealkylations. V8rik 17:06, 12 July 2007 (UTC)
 * I think the text needs some re-working to more effectively convey that this is the result of a series of alkylations and dealkylations, as a chemistry student I was almost thrown off by this
 * I have made the text more clear V8rik 19:37, 12 August 2007 (UTC)

drugfuture.com
Sorry, but "drugfuture.com" links point to an illegal copy of the Merck index. I have already contacted Merck about the issue. 213.188.227.119 (talk) 15:08, 29 November 2007 (UTC)

F-C cyclization
the helicene article talk about Friedel-Crafts cyclization... what's that? —Preceding unsigned comment added by 72.70.182.227 (talk) 15:33, 16 June 2008 (UTC)

Friedel–Crafts acylation
I do not think, that the "catalyst" is regenerated. Most Friedel-Crafts acylations use stoichiometric amounts of lewis acid. For learning purposes it is not helpful, if people think, catalytic amounts of AlCl3 can be used. Maybe the full mechanism needs to be rechecked. There are two versions available in common textbooks and I can't judge by myself whether you have chosen the more reliable one. So the main question is, whether AlCl3 is bound to Cl or to O before formation of the acylium ion... 213.188.227.119 (talk) 02:58, 4 January 2012 (UTC)
 * Good question, but yes the catalyst is regenerated. The evolved HCl should not diminish its activity, but yes if one is acylating the resulting ketone would be a better Lewis base than the acyl chloride and slow it.  But I have not seen that it kills it.  The more grevious problems with the page are the depiction of FeX4- as square planar (probably a bitetrahedral dimer Fe2X7-) and the naked carbocation. Nice point overall because many so-called catalysts are not very catalytic. --Smokefoot (talk) 03:10, 4 January 2012 (UTC)

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Why is sulfonation listed here?
The FC reaction refers to construction of C-C bonds with electrophilic carbon. I've never seen the FC reaction used to refer to sulfonation or any other C-X bond forming reaction. It's like how people call any 1,4-addition a Michael reaction these days. If there's agreement on this issue, I move to delete this section, or merge this into the article on electrophilic aromatic substitution. Btw, is there an easy way to transfer text from one article to another? Alsosaid1987 (talk) 14:52, 29 August 2018 (UTC)
 * Question: Why is sulfonation listed here? Ans: because well-intentioned editors thought that RSO2Cl etc + ArH is an example of Friedel-Crafts repertoire without checking sacred tomes. In any case, I moved the offending section to sulfones and sulfoxides.--Smokefoot (talk) 17:29, 29 August 2018 (UTC)

Why formyl chloride is unstable?
This compound is found to be unstable at room temperature. Chlorine is a good leaving group and the hydrogen left is very acidic. The hydrogen also donates it's electron and forms HCl. In the first place, we create HCOCl by simply putting HCl and CO under high pressure. At normal conditions they go back to their constituents according to Le Chatelier's principle. 2405:201:C02C:E107:1060:510C:702:D018 (talk) 18:04, 19 February 2023 (UTC)

Largest scale reaction? production of EtPh, and other possible considerations
Many seem to emphasize alkylations of arenes with alkyl chlorides, and such reactions are indeed very instructive. But I suspect that those kinds of reactions are small change compared to alkylations using alkenes and even alcohols. Solid acids are also probably greener cheaper than AlCl3. Such commercial technologies are just not well suited for university teaching labs, so they are less often taught.--Smokefoot (talk) 22:08, 19 April 2023 (UTC)

 * I agree they're really important to include and showcase. It's just that the solid acid examples shown are only representative of Alkylation.
 * While the method using Halide's does both Alkylation and Acylation, and is the most commonly known and understood by the average reader. This doesn't mean we avoid the less known or more complex topics, just that it serves as good way to establish the reaction in the introductory section. LoomCreek (talk) 20:18, 21 April 2023 (UTC)

title: Talk:Friedel–Crafts reaction


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List of high schools in New York City

This is a list of high schools in New York City.

license: Creative Commons - Attribution Share-Alike - https://creativecommons.org/licenses/by-sa/4.0/

title: List of high schools in New York City


text:
Sampooranathevan

Sampooranathevan is a mythical figure found in Ayyavazhi mythology. He was considered a powerful Deva of Deiva Loga. In Kali Yuga, He was born, and became known in history as Mudisoodum Perumal or Muthukutty.

The exact date of birth of Mudisoodum Perumal or Muthukutty is unknown. It is mostly placed in either 1810 or 1809, while others follow the view of Akilam.

Para Devathai
Sampooranathevan of Deiva Loga and Paradevathai of Yama Loga had fallen in love. So, when Sampooranathevan asked Thirumal to be granted birth into the world, he requested the same be given to his lover. Paradevathai earlier had been married to a man of Yama Loga, but since had left him.

Thirumal refused, asserting that Para Devathai was already a wife, and that Sampooranathevan was from Deiva loga and she was from Yama Loga (a class difference). Thirumal stated that Sampooranathevan's physical birth would be great but hers would not, so Sampooranathevan's was wrong, encouraging Sampooranathevan to drop the matter. However Sampooranathevan replied, "Your Highness, only at the most lovable place does the Ultimate love (love towards God) begin and not at a random place. [Implying that his love was of divine origin.] Isn't that true? So, please fulfill my desire. Also, I promise to you, I will be most affectionate to her." [bracket added by editors] So Thirumal allowed them to perform austrity, to take birth united and sublime.

Failure of Tavam
Sampooranathevan and Para Devathai began performing austrity. When their tavam was close to an end, they saw Indra going that way. Until then their tapas had not met with any problem. But on seeing Indra a desire originated in the mind of Sampooranathevan. He asked Paradevathai, " My dear, it will be fine if you and I, with the crown of Indra, rule the world." Paradevathai replied: "Fine dear, but even if Brahma created us like that, may it be eternal." She was pointing out to him his libidinious enjoyment.

Meanwhile, in Kailai, Sivan and Thirumal were discussing how to destroy Kali, after sending Lakshmi to grow as magaram in the sea, to give birth to a child for destroying Kali (She was also asked to perform austrity in the sea). Thirumal told him about Sampooranathevan and Paradevathai and about their tavam. He also said that it was time for the closure of their tavam and time to offer birth to them, and he suggested that they all go together to them. Thirumal and Sivan came to see the tavam. On seeing them Sampooranathevan and Paradevathai welcomed and praised them.

At the very first moment of seeing them, Sivan told Thirumal that their tavam met with failure, as they had desired the crown of Indra. On hearing this Thirumal asked Sampooranathevan to illustrate. But he wondered : "I only speak of my thought with my lady with my eyes. We only communicate from mind to mind. Your greatness, How were you able to sense that." In saying this he fell on the feet of Sivan and Thirumal and asked them to excuse the misdeed. Paradevathai too cried for their rescue. They still implored Sivan and Thirumal to unite them.

Birth of Paradevathai
On seeing this Thirumal told Paradevathai that since your austrity met with failure, and because of your previous husband's sufferings due to your separation, you will be born in the world in Yamakulam and will be married to your husband of Yama Lokam. You will suffer there. You will fall ill and live without any happiness. You will not have any bodily relations with him. But still you will do all your duties to him as per the karma. At that time Sampooranathevan will be born in the world in Devakulam and will lead a joyful life in the world. Due to your previous intimacy you two will meet each other and will fall in love with each other. You will not take care of God, your father, mother, or relations, and you will consider Sampooranathevan as your husband. You will suffer due to your defamation by others. Then you will seek supreme bliss and will realise (the Ultimate real truth) God and you will be granted moksha. By saying this she was born in the world.

Acceptance of Sampooranathevan
Thirumal told Sampooranathevan that his request for Paradevathai's birth had been granted. Sampooranathevan praised them and also requested that they pardon his sin (desiring the crown of Indra). Mayon replied that, she, Paradevathai, fell in love with you even though her husband was alive. That is a sin. You performed tavam to purify her. It too failed. So you too must be born in the world and suffer like her. There, due to your deep love for her, your mind will tend to commit suicide without unifying with her. You and Paradevathai will live as husband and wife. At that time I will come and take you and transform you and give you birth as my son. And by you, I will wipe out my sorrows due to the sufferings of The Santror.

Sampooranathevan replied: "Your greatness, I was asked to be born in the world which is full of evil and sorrows. I request that you create me in the primitive Santror race. I also request that you save not only me but also the santror makkal among whom I am going to be born. And he asked Thirumal to say when he would go into the world to rescue him. Thirumal replied that he would be created in the world in the Santror race in Devakulam, and he pointed out some events which would take place in the world at the time of his arrival. Then Sampooranathevan praised Sivan and Thirumal and was born."

Birth of Sampooranathevan
The year as well as the exact date of birth of Sampooranathevan is a matter of conflict. Various historians place the year of birth as 1809 C.E while as few other sources placed his birth in 1808 C.E. The soul of Sampooranathevan was to be given birth in the world in a human body. Historians predict various dates from 12 March to 19 April. He has born as the second son to Ponnumadan - Kakaachi (also known as Veyilai) couple. The child was given birth by Kakachi, wife of Ponnu Nadar. This child grew and became known in history as Muthukutty.

Life of Sampooranathevan
Sampooranathevan also known as Muthukutty was born in 1809 to Ponnu Nadar and Veyilal Amma at Poovandanthope in the Kanyakumari District (part of Travancore then). They initially named the child Mudisoodum Perumal, meaning "Lord with a crown". But the people complained to authorities about the name and they forced the parents to change his name to Muthukutty.

The boy was initially named Mudisoodum perumal, but due to the pressure from higher castes the name was changed to Muthukutty. He started his life as a palm climber. He met Paradevathi and lived like a husband with his wife. Paradevathi soon gave birth to a son, but it was claimed that her first husband was the father. Akilam does not say anything about any birth.

Muthukutty was a religious boy who had special interest in Lord Vishnu. The holy book Akilathirattu mentions that he set a pedestal for Lord Vishnu in his house. Aged seventeen, Muthukutty started to live with Thirumalammal from the nearby village of Puviyur and she lived with him only to serve him during his public activities. Thirumalammal had been married, but left her former husband to marry Muthukutty. According to quotes found in Akilathirattu, they had a male child, who was sired by her first husband. Muthukutty earned his living as a Palmyra palm climber and as an agricultural laborer.

At the age of 17 he married [30] a woman Thirumalammal of Puviyoor, Agastheeswaram, who was left alone by her husband. There is also a view that they never get married and that the women only came to serve him in his activities. He continued his early life as a Palmyra Climber and as an Agricultural labourer. At the age of 22 he fall ill.

There is another narrative that at his age of 16, the upper classes, being irritated by the inclusionary views and activities of Vaikundar and his popularity, made several attempts to eliminate him and all of them failed. So they eventually conspired to kill him in by clandestine means. They pretend to be get convinced to his view and pretend to celebrate him and his preachings. They invited him for a banquet at Marunthuvazh Malai. He was served with poison through food.

Muthukutty in his twenty-fourth year, he was struck by illness and suffered for a year. At this time, and in a dream of his mother Lord Narayana asked her to take her son to Thiruchendur temple. His mother took her sick son to the temple at Thiruchendur, during a festival there. He went into the sea and disappeared. The parents searched for his body for one day. According to the legend, the day itself inside the sea Muthukutty also known as Sampooranathevan was granted moksha by Lord Narayana.

title: Sampooranathevan


text: File:Mac Dre - Thizzelle Washington.jpg

title: File:Mac Dre - Thizzelle Washington.jpg


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Talk:OGRE3D

Should this be REDIRECTED to OGRE_Engine? --Kricke 12 june 2005

title: Talk:OGRE3D


text:
Wikipedia:Articles for deletion/Jon Cooke

 This page is an archive of the discussion about the proposed deletion of the article below. This page is no longer live. Further comments should be made on the article's talk page rather than here so that this page is preserved as an historic record. The result of the debate was delete --cesarb 22:57, 22 Jun 2005 (UTC)

Jon Cooke
Name paired with sharp doesnt' return any relevant results. Probably vanity.

Delete

lots of issues | leave me a message 20:30, 12 Jun 2005 (UTC)

 * Let's see. He is "well respected in the world of telecommunactions, holding senior positions in many companies, most notably Sharp Corporation."  That's all very nice, but not worthy of an article. Sonic Mew 20:34, Jun 12, 2005 (UTC)
 * Speedy Hoax. Highly unlikely that anyone whould hold senior positions in many companies (except for Board of Directors).  Highly unlikely that a 25 year old would have a position in a large company senior enough to be notable.  --Xcali 20:40, 12 Jun 2005 (UTC)
 * Delete - probable hoax. --FCYTravis 22:57, 12 Jun 2005 (UTC)
 * Delete unverifiable. JamesBurns 04:42, 13 Jun 2005 (UTC)

 * This page is now preserved as an archive of the debate and, like some other VfD subpages, is no longer 'live'. Subsequent comments on the issue, the deletion, or the decision-making process should be placed on the relevant 'live' pages.  Please do not edit this page .


text:
User talk:ADINSX

ADINSX Home
HI MY NAME IS Yurivish AND I AM A NOOBLET

Oh yeah well YOUR real name is ADINSX and U R A Nublet mirite.

-

Well, Uh, umm, yer mom goes to College! Oh! What now!

You win. :(

- ADINSX: An idiot. Its natural habitat is mainly on the Internet. Strangely, this being possesses no common sense, and, consequently, fails at life.

SALAD DODGER POONS LIKE POTATOES!

YURIVISH POONS LIKE COLD PIZZA!

EXCEPT COOLER!

ICE ICE BABY :?

-

Maybe I should clarify something about this first: Yurivish called me a n00b first. Not me him.

Anyway, on with the meaningless crap, that is most likely to piss everyone at wikipedia off if they find it.

-

00:53, 5 April 2006 (UTC)

OMG! Liek teh lolz!!1 Im liek sux. ZOMG!!!1!!one!!!Eleven!!!

This "thread" is now officailly labeled as spam by me. But I still think it's hilarious. ;)

title: User talk:ADINSX