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While nucleophilic acyl substitution reactions can be base-catalyzed, the reaction will not occur if the leaving group is a stronger base than the nucleophile (i.e. the leaving group must have a higher pK a than the nucleophile). Unlike acid-catalyzed processes, both the nucleophile and the leaving group exist as anions under basic conditions.
This type of reaction is also called a 1,2-nucleophilic addition. The stereochemistry of this type of nucleophilic attack is not an issue, when both alkyl substituents are dissimilar and there are not any other controlling issues such as chelation with a Lewis acid, the reaction product is a racemate. Addition reactions of this type are numerous.
Without added salt the main products are alcohol B (42%) from nucleophilic addition to the carbonyl group and diene C (48%) as its dehydration reaction product. With added salt the main product is 1,4-adduct A (82%) with some C (7%). A 1,6-addition is also possible, for example in one step of the commercial-scale production of fulvestrant: [12]
Two common modes of Lewis acid catalysis in reactions with polar mechanisms. In reactions with polar mechanisms, Lewis acid catalysis often involves binding of the catalyst to Lewis basic heteroatoms and withdrawing electron density, which in turn facilitates heterolytic bond cleavage (in the case of Friedel-Crafts reaction) or directly activates the substrate toward nucleophilic attack (in ...
Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polarity , unless the alkene is activated with special substituents .
In the case of enone substrates, where two sites of nucleophilic addition are possible (1,2 addition to the carbonyl carbon or 1,4 conjugate addition to the β carbon), most highly reactive organolithium species favor the 1,2 addition, however, there are several ways to propel organolithium reagents to undergo conjugate addition. First, since ...
Compared to a ketone, the polarization of an oxocarbenium ion is accentuated: they more strongly resemble a "true" carbocation, and they are more reactive toward nucleophiles. In organic reactions, ketones are commonly activated by the coordination of a Lewis acid or Brønsted acid to the oxygen to generate an oxocarbenium ion as an intermediate.
The mechanism of the Michaelis–Arbuzov reaction. The Michaelis–Arbuzov reaction is initiated with the S N 2 attack of the nucleophilic phosphorus species (1 - A phosphite) with the electrophilic alkyl halide (2) to give a phosphonium salt as an intermediate (3).