Nucleophilic addition

A reaction in which a nucleophile bonds to an electrophilic multiple bond, adding across it and reducing the bond order. It commonly converts carbonyl groups into tetrahedral products.

Nucleophile: An electron-pair donor that forms a bond with an electron-pair acceptor. It supplies the electron pair that attacks the electrophilic multiple bond.
Electronegativity: A measure of an atom's tendency to attract shared electrons in a chemical bond. The oxygen–carbon electronegativity difference polarizes the carbonyl bond.
Cyanohydrin formation: The addition of hydrogen cyanide to an aldehyde or ketone, producing a cyanohydrin. It adds cyanide and a proton across a carbonyl bond.
Nucleophilic acyl substitution: A reaction at an acyl carbon in which a nucleophile replaces a leaving group. Unlike simple addition, collapse of its tetrahedral intermediate expels a substituent and reforms the carbonyl.
Aldehyde: An organic compound containing a terminal carbonyl group bonded to at least one hydrogen. Aldehydes commonly undergo addition and are generally more reactive than ketones.
Electrophile: A species that accepts an electron pair when forming a chemical bond. The polarized multiple bond contains the electron-poor site attacked in the addition.
Bond polarity: Unequal sharing of bonding electrons that gives bonded atoms partial charges. Partial charges identify the electrophilic atom targeted during addition.
Grignard reaction: A carbon–carbon bond-forming reaction in which a Grignard reagent adds to an electrophile, commonly a carbonyl compound. Grignard reagents add carbon groups to carbonyls, often forming alcohols after workup.
Electrophilic addition: A reaction in which an electrophile and a nucleophile add across an unsaturated bond. It begins with electrophilic attack on an electron-rich bond, reversing the usual polarity pattern.
Ketone: An organic compound whose carbonyl carbon is bonded to two carbon groups. Ketones undergo carbonyl addition, with steric and electronic effects shaping their reactivity.

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