In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. Organic chemistry is the scientific study of the structure, properties, composition, reactions, and synthesis of organic compounds that by definition contain carbon. ... An addition reaction, in chemistry, is in its simplest terms a organic reaction where two or more molecules combine to form a larger one. ... A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... Electron atomic and molecular orbitals, showing a Pi-bound at the bottom left of the picture In chemistry, pi bonds (Ï€ bonds) are bonds with a single nodal plane containing the line segment between the two species. ... Covalently bonded hydrogen and carbon in a molecule of methane. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ...

Addition reactions are limited to chemical compounds that have multiply-bonded atoms:

• molecules with carbon - hetero multiple bonds like carbonyls, imines or nitriles
• molecules with carbon - carbon double bonds or triple bonds

In organic chemistry a hetero atom refers to nitrogen, oxygen, sulfur, and the halogens. ... In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ... A nitrile is an organic compound which has a -CN functional group. ... Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ... Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ...

Addition to carbon - hetero double bonds

Addition reactions of a nucleophile to carbon - hetero double bonds such as C=0 or C=N show a wide variety. These bonds are very polar (large difference in electronegativity) and carbon carries a partial positive charge. This makes this atom the primary target for the nucleophile. Chemical polarity refers how polar a chemical bond is. ... Electronegativity is the measure of the ability of an atom or molecule to attract electrons in the context of a chemical bond. ...

YH + R₁R₂C=0 → YR₁R₂C-O^- + H⁺ → YR₁R₂C-OH

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, the reaction product is a racemate. Addition reactions of this type are numerous. With a carbonyl compound as an electrophile, the nucleophile can be: Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecules. ...

• water in hydration to a gemdiol (hydrate)
• an alcohol in acetalisation to an acetal
• an hydride in reduction to an alcohol
• an aliphatic amine to an imine
• an aromatic amine to a Schiff base
• a enolate ion in an Aldol condensation
• an organometallic nucleophile in the Grignard reaction or the related Barbier reaction

With miscelleneous electrophiles: In chemistry, hydration is the condition of being combined with water. ... Acetalisation is an organic reaction that involves is the formation of an acetal or ketal. ... An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... A hydride is a chemical compound of a hydrogen with other elements. ... A reducing agent is a substance used in electrochemistry that reduces another substance. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ... A Schiff base is a functional group or type of chemical compound containing a carbon-nitrogen double bond with the nitrogen atom connected to a aryl group . ... Enol (or, more officially, but less commonly: alkenol) is an alkene with hydroxyl group on one of the carbon atoms of the double bond. ... An aldol reaction takes the following form: 2 enolate anions ↔ aldol The reaction requires a base catalyst. ... Organometallic have classically been compounds having bonds between one or more metal atoms and one or more carbon atoms of an organyl group. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... The Barbier reaction is an organic reaction between a alkyl halide and a carbonyl group as an electrophilic substrate in the presence of aluminium, zinc, indium, tin or its salts. ...

• hydrolysis of a nitrile to a amide or a carboxylic acid
• addition of an alcohol to a isocyanate to form a urethane

The nitrile group is an electrophile in the Blaise reaction with organozinc nucleophiles and with alcohols in the Pinner reaction. A nitrile is an organic compound which has a -CN functional group. ... In chemistry, the term amide has several meanings. ... Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. The salts and anions of carboxylic acids are called carboxylates generally. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... Isocyanate is the chemical group of atoms -N=C=O (1 nitrogen, 1 carbon, 1 oxygen), as opposed to cyanate, -O-C≡N, which is formed from cyanogen in the normal -ate manner. ... Urethane 1. ... A nitrile is an organic compound which has a -CN functional group. ... In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a substance. ... The Blaise reaction is a chemical reaction that forms a β-ketoester from the reaction of zinc metal with a α-bromoester and a nitrile. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... The Pinner reaction is a chemical reaction of a nitrile with an alcohol under acid catalysis. ...

Addition to carbon - carbon double bonds

Y-Z + -C=C- → Y-C-C-Z

The driving force for this reaction is the formation of an nucleophile Y^- that forms a covalent bond with a electron-poor unsaturated system -C=C- (step 1). The negative charge on Y is transferred to the carbon - carbon bond. In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... Covalently bonded hydrogen and carbon in a molecule of methane. ... The term saturation generally means thoroughly full, and can refer to the following: In chemistry, see saturation (chemistry) for a number of meanings. ...

step (1) Y^- + -C=C(X)-Z → Y-C-C(X)^--

In step 2 the negatively charged carbanion combines with (Z) that is electron-poor to form the second covalent bond. A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. ...

step (2) Y-C-C(X)^-- + Z → Y-C-C(X)-Z

Ordinary alkenes are not susceptible to a nucleophilic attack (apolar bond). Styrene reacts in toluene with sodium to 1,3-diphenylpropane ^[1] through the intermediate carbanion: Styrene (also vinyl benzene, ethenylbenzene, phenethylene, cinnamene, diarex HF 77, styrolene, styrol, styropol) is an organic compound which is an aromatic hydrocarbon having the chemical formula C8H8. ... Toluene, also known as methylbenzene or phenylmethane is a clear water-insoluble liquid with the typical smell of paint thinners, reminiscent of the sweet smell of the related compound benzene. ... General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Atomic mass 22. ...

Ph-CH₃ + Na → Ph-CH₂^- + NaH

Ph-C=CH₂ + Ph-CH₂^- → Ph-CH₂CH₂CH₂-Ph

When X is a carbonyl group like C=0 or COOR or a cyanide group (CN), the reaction type is a conjugate addition reaction. The substituent X helps to stabilize the negative charge on the carbon atom by its inductive effect. In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... A cyanide is any chemical compound that contains the group C≡N, with the carbon atom triple bonded to the nitrogen atom. ...

In addition when Y-Z is a active hydrogen compound the reaction type a Michael reaction. A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. ... The Michael reaction is an intermolecular aldol reaction followed by a base catylized elimination reaction. ...

Perfluorinated alkenes (alkenes that have all hydrogens replaced by fluorine) are highly prone to nucleophilic addition, for example by fluoride ion from caesium fluoride or silver(I) fluoride to give a perfluoroalkyl anion. General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance pale greenish-yellow gas Atomic mass 18. ... Overview Caesium fluoride (cesium fluoride in North America), is an ionic compound usually found as a hygroscopic white solid. ... Silver(I) fluoride Silver(I) fluoride (AgF), also known as argentous fluoride, is a compound of silver and fluorine. ...

References

• ^[1] Sodium-catalyzed Side Chain Aralkylation of Alkylbenzenes with Styrene Herman Pines, Dieter Wunderlich J. Am. Chem. Soc.; 1958; 80(22)6001-6004.
• March jerry; (1885). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. ISBN 0-471-85472-7