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Topic: Electrophilic substitution


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In the News (Tue 21 May 19)

  
  Aromatic Reactivity
This activation or deactivation of the benzene ring toward electrophilic substitution may be correlated with the electron donating or electron withdrawing influence of the substituents, as measured by molecular dipole moments.
For example, electrophilic chlorination of toluene occurs hundreds of times faster than chlorination of benzene, but the relative rates are such that the products are 60% ortho-chlorotoluene, 39% para and 1% meta-isomers, a ratio similar to that observed for nitration.
A practical concern in the use of electrophilic aromatic substitution reactions in synthesis is the separation of isomer mixtures.
www.cem.msu.edu /~reusch/VirtualText/benzrx1.htm   (2788 words)

  
 Electrophilic aromatic substitution - Wikipedia, the free encyclopedia
Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually Hydrogen, in an aromatic system is replaced by an electrophile.
In the multistep Lehmstedt-Tanasescu reaction, one of the electrophiles is a N-nitroso intermediate.
Examples of electrophilic substitutions to pyrrole are the Pictet-Spengler reaction and the Bischler-Napieralski reaction.
en.wikipedia.org /wiki/Electrophilic_aromatic_substitution   (1184 words)

  
 Electrophilic Substitution Mechanisms Menu   (Site not responding. Last check: 2007-09-11)
The mechanism for the substitution of an acyl group such as CH CO into benzene.
The mechanism for the substitution of an alkyl group such as CH into benzene.
The mechanism for the substitution of an alkyl group such as CH into benzene, by a reaction involving an alkene such as ethene.
www.chemguide.co.uk /mechanisms/elsubmenu.html   (154 words)

  
 Electrophilic substitution - Wikipedia, the free encyclopedia
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces another group, typically but not always hydrogen.
Electrophilic aromatic substitution is an important way of introducing functional groups on benzene rings.
In electrophilic substitution in aliphatic compounds an electrophile displaces a functional group.
en.wikipedia.org /wiki/Electrophilic_substitution   (185 words)

  
 Electrophilic Aromatic Substitution
In electrophilic aromatic substitution, the benzene ring acts as an electron donor (Lewis base or nucleophile) and reacts with an electron acceptor (Lewis acid or electrophile).
In nucleophilic aromatic substitution, halogens are substituted by a nucleophile only if the aryl halides have electron-withdrawing groups in a position ortho or para to the halogen.
Electrophilic substitutions are favored by electron-donating groups which stabilize the carbocation intermediate.
www.chem.latech.edu /~deddy/chem252/EAS.htm   (1241 words)

  
 What is electrophilic substitution?
Electrophilic substitution happens in many of the reactions of compounds containing benzene rings - the arenes.
The electrophile will either be a positive ion, or the slightly positive end of a polar molecule.
In most of benzene's reactions, the electrophile is a positive ion, and these reactions all follow a general pattern.
www.chemguide.co.uk /mechanisms/elsub/whatis.html   (909 words)

  
 Electrophilic Substitution of 3-(m-Chlorophenyl)sydnone and 3-(m-Bromophenyl)sydnone   (Site not responding. Last check: 2007-09-11)
Substitution on the ortho-position of the aryl ring (see Y in structure 1 below) and the 4-position of the sydnone ring (see Z in structure 1) would allow future preparation of fused-ring congeners (2) an active area of study.
Substitution of these sydnones involved cooling a solution of the sydnone (100 mg) dissolved in freshly distilled THF (5 mL) utilizing a liquid nitrogen/chloroform bath (-63 oC) under an atmosphere of nitrogen.
electrophile) since it was proven that this proton is successfully removed in the disubstitution reactions and that the sydnone proton is selectively removed with 1.1 eq.
www.heidelberg.edu /depts/chm/sydnone.html   (4015 words)

  
 ORGANIC CHEMISTRY MECHANISMS AROMATIC HYDROCARBONS derivative Arenes electrophilic substitution concentrated conc. ...
The electrophilic substitution of an arene - nitration
Like alkenes, arenes are susceptible to electrophilic attack because of the high electron density of the pi electrons involved in the carbon-carbon bonding and both show little reactivity towards nucleophilic reagents.
The electrophilic substitution of an arene - chlorination
www.wpbschoolhouse.btinternet.co.uk /page06/OrgMechs4.htm   (1771 words)

  
 Synthesis And Electrophilic Substitution of Pyrido[2,3,4-kl]acridines
A major target in the present investigation was the study of the electrophilic substitution of pyridoacridines for the preparation of derivatives for structure activity relationship studies.
In compounds 17a and 17b only one of rings A or E was attacked by the electrophile at the para position; their structures are tentatively suggested on the basis of the structure of compound 14 as depicted in Scheme 4.
Because of the nitro groups at the ortho positions, it was impossible to prove by NOE that the substitution is at the para position of ring A (as in the case of compound 14).
pages.unibas.ch /mdpi/ecsoc-4/a0029/a0029.htm   (1349 words)

  
 C 2131 Electrophilic Aromatic Substitution Reactions
The characteristic reactions of aromatic compounds are the electrophilic aromatic substitution reactions.
The major differences are that the electrophile involved must be a very strong electrophile (very electron deficient) and that the aromatic ring must be regenerated in the final step of the reaction.
energetically speaking, the transition state corresponds to the attack on the electrophile, there is a slight trough where the resonance stabilized carbocation intermediate resides, another transition state as the proton is abstracted and finally a plateau corresponding to the final product.
www.mta.ca /~acockshu/c2131aromsubst.html   (1395 words)

  
 Electrophilic Substitution in Benzene, Nitrobenzene and Phenol
Commonly benzene and its derivatives undergo electrophilic substitution reactions in which the delocalised system in the product molecules is restored.
Activating groups direct substitution to positions to 2- and 4- (and 6-) of the benzene ring.
In the coupling reaction, with an alkaline solution of phenol, the benzene diazonium ion becomes a sufficiently powerful electrophile to react with the benzene ring forming an azo-dye via an electrophilic substitution reaction.
www.avogadro.co.uk /brief_topics/benzno2oh.htm   (653 words)

  
 Electrophilic Substitution   (Site not responding. Last check: 2007-09-11)
Electrophilic substitution reactions therefore characterise the chemistry of benzene.
As a result of the electrophile attacking and then adding to the benzene ring, an unstable intermediate is formed which carries a positive charge and in which the delocalised system of electrons is momentarily disrupted.
As an example, consider the substitution of bromine into the benzene ring.
www.avogadro.co.uk /organic/elec-sub.htm   (195 words)

  
 Electrophilic Aromatic Substitution
Groups that donate electron density (alkyls, those with a lone pair at the point of attachment, those with less electronegative atoms connected to the atom of attachment) stabilize the carbocation intermediate that is formed during ortho and para electrophilic aromatic substitution, so these positions are favored.
There is no extra stability associated with the carbocation intermediate that is formed during meta substitution, so this position is not favored.
There is no extra instability associated with the carbocation intermediate that is formed during meta substitution, so this position is favored.
www.uwlax.edu /faculty/czerwinski/eas2.htm   (451 words)

  
 Electrophilic Aromatic Substitution   (Site not responding. Last check: 2007-09-11)
The objective of this exercise is to explain the observed effects of ortho-para and meta directing substituents of electrophilic aromatic substitution in terms of the partial charge on each aromatic carbon atom.
Similarly, determine whether -CH is ortho-para directing or meta-directing substituent for electrophilic aromatic substitution.
Thus, these positions become activated towards electrophilic aromatic substitution, and the CH group is an ortho-para director, as we learned in organic chemistry.
www.webmo.net /curriculum/eas/eas_key.html   (226 words)

  
 [No title]
Electrophilic Aromatic Substitution by Paul R. Young at the University of Illinois at Chicago
Substitution (of a hydrogen) occurs in order to retain aromaticity.
The mechanisms of most electrophilic aromatic substitution reactions are very similar.
www.mpcfaculty.net /ron_rinehart/12A/chp12pag.htm   (1512 words)

  
 Electrophilic Substitution   (Site not responding. Last check: 2007-09-11)
Generation of the electrophile follows one of two pathways, depending upon whether a Bronsted acid or a Lewis acid is present:
The mechanism of the actual attack and re-aromatization is consistent regardless of electrophile:
The number of possible reagents from which to generate the electrophile is quite large.
chemistry.umeche.maine.edu /Solving/E-sub.html   (78 words)

  
 ELECTROPHILIC AROMATIC SUBSTITUTION:   (Site not responding. Last check: 2007-09-11)
Electrophilic aromatic substitution (EAS) is one of the primary methods for functionalizing aromatic rings.
A wide variety of EAS reactions exist and the one you will be studying in this lab is nitration (see pp 576-7 in your text, there is a cool animation of this reaction at: www.cm.utexas.edu/groups/iverson/eashm2.htm).
Two substituted aromatic rings will be nitrated: veratrole and methyl benzoate.
web.centre.edu /muzyka/organic/lab/NITRATIONLAB.htm   (603 words)

  
 Electrophilic Aromatic Substitution   (Site not responding. Last check: 2007-09-11)
The common explanation for the substituent effect in electrophilic aromatic substitution, is based on the relative stability of the intermediates, which are close to the transition state.
This, in turn, is founded on the accommodation of the positive charge by the substituents.
On the left it is seen how mesomeric electron donors at the o/p positions stabilize the intermediate, and thereby enhance the reaction.
cheminf.cmbi.ru.nl /wetche/organic/eas/charexpl.html   (125 words)

  
 Electrophilic Aromatic Substitution
–system towards electrophiles compared with that of alkenes.
Reaction with electrophiles results in overall substitution since this retains aromaticity in the product.
This is in contrast to electrophilic addition reactions of alkenes.
users.ox.ac.uk /~mwalter/web_05/year1/aromatic1/el_arom_subst.shtml   (115 words)

  
 Ch12 : Electrophilic Aromatic Substitution
Now it is time to visit their chemical reactions.
A substitution implies that a group is replaced (usually H).
Electrophilic aromatic substitution reactions are the very important class of reactions that allow the introduction of substituents onto arenes.
www.chem.ucalgary.ca /courses/351/Carey5th/Ch12/ch12-0.html   (112 words)

  
 CFCC Organic Chemistry   (Site not responding. Last check: 2007-09-11)
Formation of Electrophiles Herman Ammon, University of Maryland
Electrophilic Aromatic Substitution UIC (PDF file) contributed by Dante Veal
Electrophilic Aromatic Substitution 1.7 M Quicktime movie, McMaster U. Prentice-Hall Quicktime Movies:
www.tfn.net /~pendarr/aromatic.html   (168 words)

  
 Medical Dictionary: Electrophilic substitution - WrongDiagnosis.com
The following terms can be used for Electrophilic substitution
Information provided on this site is for informational purposes only; it is not intended as a substitute for advice from your own medical team.
The information on this site is not to be used for diagnosing or treating any health concerns you may have - please contact your physician or health care professional for all your medical needs.
www.wrongdiagnosis.com /medical/electrophilic_substitution.htm   (156 words)

  
 Electrophilic Aromatic Substitution   (Site not responding. Last check: 2007-09-11)
Each EAS reaction will have one or more pre-steps in which a sufficiently electrophilic species is generated.
The electrophile for the reaction is shown in the lower left-hand corner of the slide.
Direct suggestions, comments, and questions about this page to Arlene Courtney, courtna@wou.edu.
www.wou.edu /las/physci/ch335/lecture/lect14.htm   (44 words)

  
 Experiment 1- Electrophilic Aromatic Substitution
CHEM 242/247 EXPERIMENT #1 - Electrophilic Aromatic Substitution
Chapter 16 "Chemistry of Benzene: Electrophilic Aromatic Substitution"
For technical assistance with this webpage, please email the Webmaster.
www.chem.umd.edu /organiclabs/Chem243/Expt01.htm   (127 words)

  
 [No title]   (Site not responding. Last check: 2007-09-11)
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classweb.gmu.edu /jschorni/chem318/brominationtoluene.ppt   (592 words)

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