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The Mannich reaction is a chemical reaction in organic chemistry and is a amino alkylation of an acidic proton placed next to a carbonyl functional group with formaldehyde and ammonia or any primary or secondary amine. The final product is a β-amino-carbonyl compound A chemical reaction is a process involving one, two or more substances (called reactants), characterized by a chemical change and yielding one or more product(s) which are different from the reactants. ...
Organic chemistry is the scientific study of the structure, properties, composition, reactions, and synthesis of organic compounds. ...
In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ...
In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ...
The chemical compound formaldehyde (also known as methanal), is a gas with a strong pungent smell. ...
Ammonia is a chemical compound with the formula NH3. ...
Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ...
History The reaction is named after Chemist Carl Mannich. A chemist is a scientist who specializes in chemistry. ...
Classification The Mannich reaction is an example of nucleophilic addition of an amine to a carbonyl group followed by elimination of a hydroxyl anion to the Mannich base. The Mannich base is an electrophile which reacts in step two in a second nucleophilic addition with a carbanion generated from a compound containing a acidic proton. The Mannich reaction is also considered a condensation reaction. Nucleophilic addition involves the addition of a nucleophile to a chemical compound. ...
In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ...
An elimination reaction is a type of organic chemical reaction in which two groups are removed from a molecule in either a one or two-step mechanism. ...
Hydroxide is a functional group consisting of oxygen and hydrogen: -O−H It has a charge of 1-. The term hydroxyl group is used when the functional group -OH is counted as a substituent of an organic compound. ...
A mannich base is the reaction product of an amine and a carbonyl compound that engage in a nucleophilic addition reaction followed by elimination to the imine salt. ...
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. ...
Nucleophilic addition involves the addition of a nucleophile to a chemical compound. ...
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). ...
A condensation reaction (also known as a dehydration reaction) is a chemical reaction in which two molecules or moieties react with each other with the concurrent loss of water or ammonia. ...
Reactants In the Mannich reaction ammonia or primary or secondairy amines are employed for the activation of formaldehyde. Tertairy amines and aryl amines stop at the Mannich base because it lacks a proton to form the intermediate imine. α-CH-acidic compounds (Nucleophiles) are Carbonyl compounds, Nitrile compounds, Acetylene compounds, aliphatic Nitro compounds, α- alkyl-pyridine compounds or Imine compounds. Ammonia is a chemical compound with the formula NH3. ...
Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ...
The chemical compound formaldehyde (also known as methanal), is a gas with a strong pungent smell. ...
An aryl is a functional group of an organic molecule derived from an aromatic compound such as benzene. ...
An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ...
In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ...
In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ...
A nitrile is an organic compound which has a -CN functional group. ...
The chemical compound acetylene, also called ethyne, was discovered in 1836 by Edmund Davy, in England; its chemical formula is C2H2 and its structure is: Acetylene is a colorless and extremely flammable gas at standard temperature and pressure, with a melting point of -80. ...
Nitro may refer to: nitro functional group, a functional group with chemical formula NO2 nitroglycerin, an extremely volatile explosive chemical compound nitromagnesium, a fertilizer. ...
Pyridine is a clear liquid with an odor that is sour, putrid, and fish-like. ...
An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ...
Products This reaction yields β-amino carbonyl compounds and Mannich base compounds. See for example tropinone. A mannich base is the reaction product of an amine and a carbonyl compound that engage in a nucleophilic addition reaction followed by elimination to the imine salt. ...
tropinone is an alkaloid, synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. In organic chemistry the synthesis is considered a milestone in total synthesis. ...
Reaction conditions The Mannich reaction requires high reaction temperatures, long reaction times and a protic solvent. Formation of undesired reaction by-product is a common phenomenon.
Reaction mechanism The Mannich Reaction has a two part reaction mechanism - Formation of the Mannich base electrophile in a nucleophilic addition
- amino alkylation of an acidic hydrogen containing compound
 A mannich base is the reaction product of an amine and a carbonyl compound that engage in a nucleophilic addition reaction followed by elimination to the imine salt. ...
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. ...
Nucleophilic addition involves the addition of a nucleophile to a chemical compound. ...
In the second step of the reaction a carbanion is generated from a CH acidic compound (in the example below malonic acid) under the influence of a base which then attacks the iminium salt in a second nucleophilic addition. 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). ...
Malonic acid (1,3-Propanedioic Acid) is the bi-carboxylic acid with structure CH2(COOH)2. ...
A base is: in mathematics: A number that is raised to a power, or base of an exponential function. ...
Nucleophilic addition involves the addition of a nucleophile to a chemical compound. ...
Applications The Mannich-Reaction is employed in the organic synthesis of natural compounds like for instance Peptides-Nucleotides-Antibiotics und Alkaloids. Other applications are in agro chemicals, paint- and polymer chemistry, catalysts and crosslinking. Organic synthesis is the construction of organic molecules via chemical processes. ...
Peptides (from the Greek πεπτος, digestable), are the family of molecules formed from the linking, in a defined order, of various amino acids. ...
A nucleotide is a monomer or the structural unit of nucleotide chains forming nucleic acids as RNA and DNA. A nucleotide consists of a heterocyclic nucleobase, a pentose sugar, and a phosphate or polyphosphate group. ...
An antibiotic is a drug that kills or slows the growth of bacteria. ...
An alkaloid is a nitrogenous organic molecule that has a pharmacological effect on humans and other animals. ...
Polymer chemistry is the scientific study of the structure, properties, composition, and reactions of polymers. ...
A catalyst (Greek: καταλύτης, catalytis) is a substance that accelerates the rate of a chemical reaction, at some temperature, but without itself being transformed or consumed by the reaction (see also catalysis). ...
References - Original translated from German Wiki
- Recent practical example: synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid Flávia A. F. da RosaI, Ricardo A. RebeloI, Maria G. NascimentoII J. Braz. Chem. Soc. vol.14 p. 11 2003[1] open access publication
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