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The reaction most often occurs at an aliphatic sp 3 carbon center with an electronegative, stable leaving group attached to it, which is frequently a halogen (often denoted X). The formation of the C–Nu bond, due to attack by the nucleophile (denoted Nu), occurs together with the breakage of the C–X bond.
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 ...
Others, however, insist that such a usage is an abuse of terminology, and limit the Michael addition to the formation of carbon–carbon bonds through the addition of carbon nucleophiles. The terms oxa-Michael reaction and aza-Michael reaction [2] have been used to refer to the 1,4-addition of oxygen and nitrogen nucleophiles, respectively. The ...
Also, because the intermediate is partially bonded to the nucleophile and leaving group, there is no time for the substrate to rearrange itself: the nucleophile will bond to the same carbon that the leaving group was attached to. A final factor that affects reaction rate is nucleophilicity; the nucleophile must attack an atom other than a hydrogen.
When a nucleophile X − adds to an alkene, the driving force is the transfer of negative charge from X to the electron-poor unsaturated-C=C- system. This occurs through the formation of a covalent bond between X and one carbon atom, concomitant with the transfer of electron density from the pi bond onto the other carbon atom (step 1). [1]
Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form.
The terms nucleophile and electrophile are sometimes interchangeable with Lewis base and Lewis acid, respectively. These terms, especially their abstract noun forms nucleophilicity and electrophilicity , emphasize the kinetic aspect of reactivity, while the Lewis basicity and Lewis acidity emphasize the thermodynamic aspect of Lewis adduct ...
A nucleophile reacts with a α,β-unsaturated carbonyl compound in the β position. The negative charge carried by the nucleophile is now delocalized in the alkoxide anion and the α carbon carbanion by resonance. Protonation leads through keto-enol tautomerism to the saturated carbonyl compound.