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Concept
Electrophile
Summary
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.
Electrophiles mainly interact with nucleophiles through addition and substitution reactions. Frequently seen electrophiles in organic syntheses include cations such as H+ and NO+, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl2 and Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH3 and DIBAL.
These occur between alkenes and electrophiles, often halogens as in halogen addition reactions. Common reactions include use of bromine water to titrate against a sample to deduce the number of double bonds present. For example, ethene + bromine → 1,2-dibromoethane:
C2H4 + Br2 → BrCH2CH2Br
This takes the form of 3 main steps shown below;
Forming of a π-complex
The electrophilic Br-Br molecule interacts with electron-rich alkene molecule to form a π-complex 1.
Forming of a three-membered bromonium ion
The alkene is working as an electron donor and bromine as an electrophile. The three-membered bromonium ion 2 consisted of two carbon atoms and a bromine atom forms with a release of Br−.
Attacking of bromide ion
The bromonium ion is opened by the attack of Br− from the back side. This yields the vicinal dibromide with an antiperiplanar configuration. When other nucleophiles such as water or alcohol are existing, these may attack 2 to give an alcohol or an ether.
This process is called AdE2 mechanism ("addition, electrophilic, second-order"). Iodine (I2), chlorine (Cl2), sulfenyl ion (RS+), mercury cation (Hg2+), and dichlorocarbene (:CCl2) also react through similar pathways.
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Markovnikov's rule
In organic chemistry, Markovnikov's rule or Markownikoff's rule describes the outcome of some addition reactions. The rule was formulated by Russian chemist Vladimir Markovnikov in 1870. The rule states that with the addition of a protic acid HX or other polar reagent to an asymmetric alkene, the acid hydrogen (H) or electropositive part gets attached to the carbon with more hydrogen substituents, and the halide (X) group or electronegative part gets attached to the carbon with more alkyl substituents.
Nucleophile
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. Nucleophilic describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic character and is often used to compare the affinity of atoms.
Alkylation
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins.