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Topic: Electrophilic addition

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	What is electrophilic addition?
		Electrophiles are strongly attracted to the exposed electrons in the pi bond and reactions happen because of that initial attraction - as you will see shortly.
		An electrophilic addition reaction is an addition reaction which happens because what we think of as the "important" molecule is attacked by an electrophile.
		The slightly positive X atom is an electrophile and is attracted to the exposed pi bond in the ethene.
	www.chemguide.co.uk /mechanisms/eladd/whatis.html (1270 words)

	Electrophilic addition - Wikipedia, the free encyclopedia
		In organic chemistry, an electrophilic addition reaction is an addition reaction where in chemical compound a pi bond is removed by the creation of two new covalent bonds.
		In electrophilic additions common substrates have a carbon-carbon double bond or triple bond.
		In all asymmetric addition reactions to carbon regioselectivity is important and often determined by Markovnikov's rule.
	en.wikipedia.org /wiki/Electrophilic_addition (215 words)

	Electrophilic addition -- Facts, Info, and Encyclopedia article (Site not responding. Last check: 2007-10-24)
		In electrophilic additions common substrates have a carbon-carbon (A covalent bond in which two pairs of electrons are shared between two atoms) double bond or (additional info and facts about triple bond) triple bond.
		The exact nature of the electrophile and the nature of the positively charged intermediate is not always clear and depends on reactants and reaction conditions.
		In all asymmetric addition reactions to carbon (additional info and facts about regioselectivity) regioselectivity is important and often determined by (additional info and facts about Markovnikov's rule) Markovnikov's rule.
	www.absoluteastronomy.com /encyclopedia/e/el/electrophilic_addition.htm (235 words)

	Addition reaction - Wikipedia, the free encyclopedia
		An addition reaction, in chemistry, is in its simplest terms a organic reaction where two or more molecules combine to form a larger one.
		An addition reaction is the opposite of an elimination reaction.
		The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, rearrangement reactions and organic redox reactions.
	en.wikipedia.org /wiki/Addition_reaction (135 words)

	Organic Chemistry at Penn State: Reactions (Site not responding. Last check: 2007-10-24)
		Electrophilic addition of hydrogen halides (HX) to alkenes.
		Electrophilic addition of halogens to alkenes in the presence of water.
		Electrophilic addition of hydrogen halides (HX) to alkynes.
	courses.chem.psu.edu /chem38/reactions/reactions.html (982 words)

	Alkene - Wikipedia, the free encyclopedia
		This is an alloy of nickel and aluminium.
		This is the catalytic hydrogenation of ethylene to yield ethane: CH Electrophilic addition: Most addition reactions to alkenes follow the mechanism of electrophilic addition.
		Addition of a carbene or carbenoid yields the corresponding cyclopropane
	en.wikipedia.org /wiki/Alkenes (1065 words)

	Encyclopedia: Electrophilic addition (Site not responding. Last check: 2007-10-24)
		In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a substance.
		An electrophilic aromatic substitution is a chemical reaction in which a hydrogen atom of an aromatic ring is replaced by an electrophile.
		A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon-carbon double bond of an alkene functional group.
	www.nationmaster.com /encyclopedia/Electrophilic-addition (773 words)

	Electrophilic Addition (Site not responding. Last check: 2007-10-24)
		Electrophilic addition is demonstrated by hydrogen halide addition to an alkene.
		Another electrophilic addition reaction is Hydration, the addition of the elements of water to an alkene.
		Molecular bromine simultaneously acts as the electrophile and the nucleophile.
	www.scientia.org /cadonline/Organic_Chem/hydrocarbons/electrophilic.ASP (492 words)

	[No title]
		In addition reactions of alkenes, the pi bond is broken and two new sigma bonds are formed.
		Addition of Aqueous Acids Like the addition of hydrogen halides, the proton adds first to the pi system and a carbocation intermediate is formed.
		It differs from the electrophilic addition reactions seen earlier in that boron is the electrophile (species attracted to the system) and adds to the least highly substituted carbon atom.
	www.geocities.com /CapeCanaveral/Lab/4433/131A/ADDNRXN.HTM (864 words)

	Electrophilic Reactions (Site not responding. Last check: 2007-10-24)
		In the electrophilic reactions we have seen, the electrophile accepts electrons from the pi-bond of an alkene or benzene generating a carbocation where the pi-bond used to be.
		Electrophilic addition involves sequentional addition of an electrophile to a pi-bond, followed by attack by a nucleophile.
		Step-by-step breakdown of the mechanism of electrophilic addition.
	www.sienahts.edu /~swathen/organic/ephilic.html (169 words)

	Chapter 8 Outline
		Electrophilic addition - The alkene attacks an electrophile resulting in a carbocation.
		Anti-Markovnikov addition - free radical addition of HX to an alkene.
		Hydrogenation - reduction of an alkene to the saturated hydrocarbon (addition of H
	www.anselm.edu /homepage/cweinreb/org/outlines/Ch8.html (186 words)

	Carbonyl Reactivity
		The fundamental transformation in this reaction is a dimerization of an aldehyde (or ketone) to a beta-hydroxy aldehyde (or ketone) by alpha C–H addition of one reactant molecule to the carbonyl group of a second reactant molecule.
		The exception, reaction #3, is conducted under mild conditions with an excess of the reactive aldehyde formaldehyde serving in the role of electrophilic acceptor.
		Modestly electrophilic reactants such as alkyl halides are not sufficiently reactive to combine with neutral enol tautomers, but the increased nucleophilicity of the enolate anion conjugate base permits such reactions to take place.
	www.cem.msu.edu /~reusch/VirtualText/aldket2.htm (3411 words)

	PSIgate - Physical Sciences Information Gateway: Search/Browse Results (Site not responding. Last check: 2007-10-24)
		The tutorial covers the fundamentals of addition polymerisation including sources of petroleum, introduction to cracking, catalytic cracking of petroleum, properties of alkanes and alkenes, example addition polymers (polyethylene), free radical polymerisation, and commercial polymers and their structure and properties.
		Electrophilic addition is introduced, with illustrated notes on the structure of ethene, electrophiles, and the electrophilic addition mechanism.
		This section covers electrophilic addition to alkenes, detailing the general mechanism with the aid of chemical diagrams, types of electrophilic addition, orientation of addition, and an example of electrophilic addition to alkenes.
	www.psigate.ac.uk /roads/cgi-bin/psisearch.pl?term1=addition&limit=0&subject=All (1581 words)

	Additions to Alkenes
		The acid catalyzed addition of water to an aldehyde is one such reaction and we studied it earlier.
		These steps -- first an electrophile attacks the pi bond to form a carbocation, second a nucleophile attacks the carbocation -- are the key steps in the most important reactions of alkenes, electrophilic addition reactions.
		is thus the electrophile and the Br is the nucleophile.
	chemistry2.csudh.edu /rpendarvis/AlkeneAddn.html (1583 words)

	Grignard Synthesis
		Later steps, which depend upon the structure of the nucleophile, determine whether the overall reaction is addition or replacement of the oxygen by the nucleophilic atom.
		Since we have learned that the carbonyl carbon of aldehydes reacts as an electrophile, we must conclude that the carbon which started out attached to the bromine is behaving as a nucleophile.
		If we look at the product of our shorthand description and remember that the addition of a Grignard reagent makes a new carbon-carbon bond in which one of the carbons is attached to an OH group, we can see that there are two such bonds (thicker and longer in the drawing) in our product molecule.
	chemistry2.csudh.edu /rpendarvis/grignard.html (1716 words)

	addition (Site not responding. Last check: 2007-10-24)
		Electrophilic addition reactions are transformations in which reagents are added to compounds containing multiple (double or triple) bonds.
		Overall, the reaction results in addition of an electrophile and nucleophile to the multiple bond.
		Essentially, the major product of addition will be the one that results from the most stable cation intermediate.
	iws.ohiolink.edu /chemistry/organic/addition.html (192 words)

	Electrophilic Addition of Polychloroalkanes to C60: Direct Observation of Alkylfullerenyl Cation Intermediates (Site not responding. Last check: 2007-10-24)
		Electrophilic Addition of Polychloroalkanes to C60: Direct Observation of Alkylfullerenyl Cation Intermediates
		We now report that the addition of a carbocation, generated from chloroform with aluminum trichloride [1.], readily occurs.
		C resulted in the addition of one molecule of chloroform, and the reaction reached completion in approximately 2 h.
	mason.gmu.edu /~sslayden/lec/313/fuller-addn/fuller-addn.htm (248 words)

	EqIsotopeEffect (Site not responding. Last check: 2007-10-24)
		The simplest case of electrophilic addition is initiated by the proton, as an electrophile, forming a bond to one of the carbons by using the pi electrons of the double bond.
		Unlike H+, all other electrophiles possess electrons, which often occupy a sufficiently high HOMO properly oriented to give an additional nucleophilic character to the initial step of the reaction.
		In favorable cases donation of the (red) pi electrons of the alkene to the LUMO of the electrophile is accompanied by "back donation) from the HOMO of the electrophile to the pi* LUMO of the alkene.
	classes.yale.edu /chem125a/125webSpring/Alkene%20Addition/AddnAnalogies.htm (755 words)

	Electrophilic Addition
		Electrophilic addition reactions are an important class of reactions that allow the interconversion of C=C and C
		The p-orbital that is not utilised in the hybrids is empty and is often shown bearing the positive charge since it represents the orbital available to accept electrons.
		As they have an incomplete octet, carbocations are excellent electrophiles and react readily with nucleophiles (substitution).
	www.mhhe.com /physsci/chemistry/carey/student/olc/ch06electrophilicaddition.html (453 words)

	Sn2
		This is followed by addition of a water molecule to the resulting carbocation.
		We have seen that the stereochemical outcome of the electrophilic addition reactions of alkenes depends upon the reaction conditions, and that both syn and anti additions have been observed.
		Regardless of whether Figure 6 accurately reflects the structure of the transition state of this reaction, the key point to remember is that the hydroboration-oxidation sequence provides a means of preparing alcohols that have the opposite regiochemistry of those prepared by acid-catalysed hydration of alkenes.
	www.usm.maine.edu /~newton/Chy251_253/Lectures/Hydroboration/Hydroboration.html (950 words)

	Understanding Chemistry - Organic Mechanisms Menu
		Free radical addition during the polymerisation of ethene and the reaction between HBr and alkenes in the presence of organic peroxides.
		Addition reactions of alkenes such as ethene and propene.
		Addition reactions of carbonyl compounds such as ethanal and propanone.
	www.chemguide.co.uk /mechmenu.html (96 words)

	addition (Site not responding. Last check: 2007-10-24)
		Electrophilic Addition reactions are transformations in which electrophilic reagents are added to compounds containing multiple (double or triple) bonds.
		Pi electrons from substrate are donated towards the electrophile, a bond is formed between one of the carbon atoms in the double bond and the electrophile.
		Donation of electrons from the pi bond to the electrophile results in carbocation formation.
	www.as.ysu.edu /~pnorris/public_html/Mechanisms/addition.htm (204 words)

	Electrophilic Addition (Site not responding. Last check: 2007-10-24)
		The reaction is completed by the subsequent addition of the anion to the carbocation (a species in which a carbon atom carries a positive charge) yielding a saturated product.
		Although the reaction mechanism involves electrophilic addition followed by nucleophilic addition, the mechanism is named after the first step.
		For the bromination of an alkene, traces of water and the surface of the glass vessel, which functions as a surface catalyst, contribute to the formation of the dipole in the Br molecule.
	www.avogadro.co.uk /organic/elec-add.htm (230 words)

	Skill Development Exercises CA 17A (Site not responding. Last check: 2007-10-24)
		In particular, explain why one disubstituted alkene in the table (2-methylpropene) undergoes electrophilic addition 100 times faster than the other disubstituted alkene in the table (trans-2-butene).
		Trans-2-butene undergoes electrophilic addition via a secondary carbocation intermediate, whereas 2-methylpropene undergoes electrophilic addition via a tertiary carbocation intermediate.
		An electrophilic addition of HX to ethane would result in a primary carbocation, which does not form.
	home.earthlink.net /~cuachemistry/organic/SDEAns/AnsSDE17A.htm (467 words)

	Electrophilic Addition (Site not responding. Last check: 2007-10-24)
		Electrophilic addition proceeds by two slightly different mechanisms, according to whether the electrophile has an unshared pair (halogen, mercury, oxygen) or not (proton, boron):
		In the first case, the nucleophilic part of the reagent attacks the more substituted end of the bridged ion; this gives the same regioselectivity as the pathway through a carbocation.
		Note that the former case results in anti- addition, whereas the latter case is not stereoselective because of the planarity of the carbocation intermediate.
	chemistry.umeche.maine.edu /Solving/E-add.html (127 words)

	ORGANIC CHEMISTRY II
		Addition of HX occurs via a carbocation intermediate generated by the protonation of a p bond
		Addition of bromine and chlorine occurs in a Markovnikov fashion when water is the solvent
		The Markovnikov addition of water to an alkyne is catalyzed by mercury (II) ion with sulfuric acid and produces a ketone
	www.muhlenberg.edu /depts/chemistry/chem202woh/exam1.htm (788 words)

	electrophilic addition reactions menu
		Covers addition to symmetrical alkenes like ethene and cyclohexene.
		A symmetrical alkene has the same groups attached to both ends of the carbon-carbon double bond.
		An explanation of the terms addition and electrophile, together with a general mechanism for these reactions.
	www.chemguide.co.uk /mechanisms/eladdmenu.html (207 words)

	[No title]
		Consider the electrophilic addition of H-Br to 2-butene: The alkene abstracts a proton from the HBr, and a carbocation and bromide ion are generated.
		Catalytic Hydrogenation This is the addition of a hydrogen molecule to a compound using a (usually Pt, Pd, Ni) catalyst.
		Addition of Carbenes Carbenes are neutral, reactive intermediates with a divalent carbon and a lone pair.
	crab.rutgers.edu /~burke/organic/Ch08.doc (3142 words)

	Addition Reactions of Alkynes
		Alkynes undergo addition reactions in an analogous fashion to those of alkenes.
		The new C-H s bonds are formed simultaneously from H atoms absorbed onto the metal surface.
		Attack of the nucleophilic water molecule on the electrophilic carbocation creates an oxonium ion.
	www.mhhe.com /physsci/chemistry/carey/student/olc/ch09additionreactionsofalkynes.html (829 words)

	[No title]
		Addition reactions by Gary Trammell and Srinivas Vuppuluri at the University of Illinois at Springfield
		Markovnikov addition by Gary Trammell and Srinivas Vuppuluri at the University of Illinois at Springfield
		Addition of Halogens by Gary Trammell and Srinivas Vuppuluri at the University of Illinois at Springfield
	www.mpcfaculty.net /ron_rinehart/12A/chap6pag.htm (1191 words)

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