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A hydroxide ion acting as a nucleophile in an S N 2 reaction, converting a haloalkane into an alcohol. 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 ...
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. [1] Because electrophiles accept electrons, they are Lewis acids. [2] 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.
In the context of a specific chemical reaction between NH 3 and Me 3 B, a lone pair from NH 3 will form a dative bond with the empty orbital of Me 3 B to form an adduct NH 3 •BMe 3. The terminology refers to the contributions of Gilbert N. Lewis. [2] The terms nucleophile and electrophile are sometimes interchangeable with Lewis base and ...
The nucleophile may be electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged. An example of nucleophilic substitution is the hydrolysis of an alkyl bromide , R-Br under basic conditions, where the attacking nucleophile is hydroxyl ( OH − ) and the leaving group is bromide ( Br − ).
An application of HSAB theory is the so-called Kornblum's rule (after Nathan Kornblum) which states that in reactions with ambident nucleophiles (nucleophiles that can attack from two or more places), the more electronegative atom reacts when the reaction mechanism is S N 1 and the less electronegative one in a S N 2 reaction.
In the first type, a nucleophile, an atom or molecule with an excess of electrons and thus a negative charge or partial charge, replaces another atom or part of the "substrate" molecule. The electron pair from the nucleophile attacks the substrate forming a new bond, while the leaving group departs with an electron pair. The nucleophile may be ...
The reaction occurs only when the occupied lone pair orbital of the nucleophile donates electrons to the unfilled σ* antibonding orbital between the central carbon and the leaving group. Throughout the course of the reaction, a p orbital forms at the reaction center as the result of the transition from the molecular orbitals of the reactants ...
This reaction is similar to nucleophilic aliphatic substitution where the reactant is a nucleophile rather than an electrophile. The four possible electrophilic aliphatic substitution reaction mechanisms are S E 1, S E 2(front), S E 2(back) and S E i (Substitution Electrophilic), which are also similar to the nucleophile counterparts S N 1 and ...