Electron-rich species that are attracted to a positively polarized atom (i.e. a carbonyl carbon)
The electron-rich species that are attracted to a positively polarized atom, such as a carbonyl carbon, are nucleophiles
The electron-rich species that are attracted to a positively polarized atom, such as a carbonyl carbon, are nucleophiles. Nucleophiles are molecules or ions that have a lone pair of electrons or a pi bond that can form a new covalent bond with a positively charged or partially positively charged atom.
In the case of a carbonyl carbon, it is partially positively charged due to the difference in electronegativity between carbon and oxygen in the carbonyl group. This partial positive charge on the carbon atom creates an electrostatic attraction for nucleophiles.
Some common examples of nucleophiles that can react with carbonyl compounds include:
1. Alcohols: Alcohols have a lone pair of electrons on the oxygen atom and can attack the carbonyl carbon to form a hemiacetal or acetal compound.
2. Amines: Amines have a lone pair of electrons on the nitrogen atom and can react with a carbonyl carbon to form an imine or enamines.
3. Grignard reagents: Grignard reagents, typically represented as RMgX, have a negatively charged carbon atom and can react with a carbonyl carbon to form an alcohol after protonation.
4. Cyanide ions: Cyanide ions, represented as CN-, are strong nucleophiles and can react with a carbonyl carbon to form a cyanohydrin compound.
5. Organolithium compounds: Organolithium compounds are another type of strong nucleophile that can attack carbonyl carbons to form alcohols or alkoxides.
The reaction between nucleophiles and carbonyl compounds is known as nucleophilic addition, where the nucleophile adds to the carbon of the carbonyl group, breaking the pi bond and forming new covalent bonds. This reaction is vital in organic synthesis and plays a key role in many important reactions such as the formation of alcohols, amines, and other functional groups.
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