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Formally, a carbanion is the conjugate base of a carbon acid: R 3 CH + B − → R 3 C − + HB. where B stands for the base. The carbanions formed from deprotonation of alkanes (at an sp 3 carbon), alkenes (at an sp 2 carbon), arenes (at an sp 2 carbon), and alkynes (at an sp carbon) are known as alkyl, alkenyl , aryl, and alkynyl anions ...
The trend of carbocation stability. Note the stabilization effects from adjacent carbons that donate electrons to the positive charge. The opposite trend is seen in carbanion stability. In isotopes, a tertiary bound hydrogen is more likely to be lost because the resulting carbocation is the most stable species. Radical reactions that cleave C ...
The nucleophilic carbanion center quickly undergoes carbolithiation to the double bond, generating an anion stabilized by the adjacent sulfone group. An intramolecular S N 2 reaction by the anion forms the cyclic backbone of morphine. [14] Synthesis of morphine using lithium–halogen exchange
Carbanion alkylation is a common strategy used to create carbon-carbon bonds. The alkylating agent is usually an alkyl halide or an equivalent compound with a good leaving group on carbon. The alkylating agent is usually an alkyl halide or an equivalent compound with a good leaving group on carbon.
Both these studies show how Bent's rule can be used to aid synthetic chemistry. Knowing how molecular geometry accurately due to Bent's rule allows synthetic chemists to predict relative product stability. [14] [30] Additionally, Bent's rule can help chemists choose their starting materials to drive the reaction towards a particular product. [14]
An example of the E1cB reaction mechanism in the degradation of a hemiketal under basic conditions. The E1cB elimination reaction is a type of elimination reaction which occurs under basic conditions, where the hydrogen to be removed is relatively acidic, while the leaving group (such as -OH or -OR) is a relatively poor one.
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All feature three contiguous sp²-hybridized carbon centers and all derive stability from resonance. [6] Each species can be presented by two resonance structures with the charge or unpaired electron distributed at both 1,3 positions. Resonance structure of the allyl anion. The cation is identical, but carries an opposite-sign charge. [7]