Name Reactions pp 106–107 Cite as
Cannizzaro reaction
- Jie Jack Li 2
- First Online: 01 January 2014
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Redox reaction between aromatic aldehydes, formaldehyde or other aliphatic aldehydes without α-hydrogen. Base is used to afford the corresponding alcohols and carboxylic acids.
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Cannizzaro, S. Ann. 1853 , 88 , 129–130. Stanislao Cannizzaro (1826–1910) was born in Palermo, Sicily, Italy. In 1847, he had to escape to Paris for participating in the Sicilian Rebellion. Upon his return to Italy, he discovered benzyl alcohol synthesis by the action of potassium hydroxide on benzaldehyde. Political interests brought Cannizzaro to the Italian Senate and he later became its vice president.
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Jie Jack Li
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Li, J.J. (2014). Cannizzaro reaction. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_51
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22 Cannizzaro Reaction
From the book organic chemistry: 100 must-know mechanisms.
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Chapters in this book (107)
15.40: Nonenolizable Aldehydes to Acids and Alcohols: The Cannizzaro Reaction
Chapter 1: covalent bonding and structure, chapter 2: thermodynamics and chemical kinetics, chapter 3: alkanes and cycloalkanes, chapter 4: stereoisomerism, chapter 5: acids and bases, chapter 6: nucleophilic substitution and elimination reactions of alkyl halides, chapter 7: alkene structure and reactivity, chapter 8: reactions of alkenes, chapter 9: alkynes, chapter 10: alcohols and phenols, chapter 11: ethers, epoxides, sulfides, chapter 12: aldehydes and ketones, chapter 13: carboxylic acids, chapter 14: carboxylic acid derivatives, chapter 15: α-carbon chemistry: enols, enolates, and enamines, chapter 16: dienes, conjugated pi systems, and pericyclic reactions, chapter 17: aromatic compounds, chapter 18: reactions of aromatic compounds, chapter 19: amines, chapter 20: radical chemistry, chapter 21: synthetic polymers.
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The Cannizzaro reaction is a redox process producing an alcohol and a carboxylic acid from two aldehyde molecules in the presence of a base.
The reaction is specific with nonenolizable aliphatic or aromatic aldehydes that contain no α hydrogens.
Aldehydes bearing α hydrogens, under basic conditions, often undergo deprotonation to give the enolate ion, followed by an aldol reaction.
Nonenolizable aldehydes endure the Cannizaro reaction pathway wherein the anion of the base attacks the carbonyl carbon, forming a tetrahedral alkoxide intermediate.
The base further deprotonates the intermediate resulting in an unstable dianionic species.
The strong electron-donating ability of O - facilitates the transfer of the aldehydic hydrogen to another aldehyde molecule.
This intermolecular hydride transfer generates an alkoxide and a carboxylate ion.
The more basic alkoxide ion is protonated by water to produce an alcohol, while the less basic carboxylate ion requires an acid workup to generate the carboxylic acid.
The Cannizzaro reaction is a disproportionation reaction where one aldehyde molecule is oxidized while the other is reduced.
The Cannizzaro reaction is a base-promoted redox reaction producing a primary alcohol and a carboxylic acid from two molecules of a nonenolizable aldehyde. The reaction commences when the anionic counterpart of the base attacks the carbonyl carbon, resulting in a tetrahedral alkoxide intermediate. The base then abstracts a proton from the intermediate to generate an unstable dianionic species. This intermediate enables the release of the aldehydic hydrogen as a hydride ion. An intermolecular hydride shift to another aldehyde molecule produces an alkoxide and a carboxylate ion. The more basic alkoxide undergoes protonation by the water molecule to form an alcohol, while the carboxylate is protonated via an acid work-up to yield a carboxylic acid. A disproportionation reaction involving two different aldehydes is called a Crossed-Cannizzaro reaction.
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View Article Online. Theoretical DFT study of Cannizzaro reaction mechanism: A mini perspe ctive. Mohammad Suhail. 1,*, Sofi Danish Mukhtar, Imran Ali, Ariba Ansari. and Saiyam Arora. Department ...
Several aldehydes undergo disproportionation into corresponding acids and alcohols (Cannizzaro reaction) over calcined hydrotalcite, magnesium aluminum layered double hydroxide (LDH), in water. The reactions are slow and ~10% conversions were achieved after stirring for 24 h at room temperature. The mixed metal oxide obtained on calcination of ...
Research activities on (photo)electrocatalytic reduction of CO 2 have therefore increased exponentially, especially in the past few years. Different reaction ... aldehydes are the most important intermediates/products, because of their diverse reactivity. The Cannizzaro reaction is a base-catalyzed disproportionation reaction of an aldehyde ...
The Cannizzaro reaction is a base-catalyzed disproportionation reaction of an aldehyde, devoid of α-H atoms, into the corresponding carboxylic acid and alcohol.21−23 Aldehydes with α-H atoms do not undergo the Cannizzaro disproportionation, as the aldol reaction is much faster. In the aldol reaction, C−C bond formation occurs
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. ... Intramolecular catalysis. Part 4. The intramolecular Cannizzaro ...
Example 4, Desymmetrization by intramolecular Cannizzaro reaction 9 References 1. Cannizzaro, S. Ann. 1853, 88 , 129 130. Stanislao Cannizzaro (1826 1910) was born in Palermo, Sicily, Italy. In 1847, he had to escape to Paris for participating in the Si-cilian Rebellion. Upon his return to Italy, he discovered benzyl alcohol synthesis by
References. Cannizzaro, S. Ann. 1853, 88, 129-130. Stanislao Cannizzaro (1826-1910) was born in Palermo, Sicily, Italy. In 1847, he had to escape to Paris for participating in the Sicilian Rebellion. Upon his return to Italy, he discovered benzyl alcohol synthesis by the action of potassium hydroxide on benzaldehyde.
1.2. Mechanisms for Cannizzaro reaction observers According mechanism, benzaldehyde a tetrahedral demonstrated mechanism undergoes nucleophilic Hydroxyl addition a second of molecule OH- ion to ...
The Cannizzaro reaction is the disproportionation of an aldehyde to on equimolar mixture of primary alcohol and carboxylic acid. The first step in the mechanism is the nucleophilic attack of the hydroxide anion on the carbonyl group of the aldehyde to give a tetrahedral intermediate, which expels hydride
Introduction. The intramolecular Cannizzaro reaction that converts glyoxals [RC(O)CHO] to the corresponding α-hydroxy carboxylic acid or esters [RCHOH(CO 2 R 1)] has been known since the end of the 19 th century. 1, 2 Through the years this transformation has been intensively explored and the harsh reaction conditions initially employed (e. g. strong bases, high temperatures) have been ...
Research activities on (photo)electrocatalytic reduction of CO 2 have therefore increased exponentially, especially in the past few years. Different reaction products have been observed depending on, e.g., ... because of their diverse reactivity. The Cannizzaro reaction is a base-catalyzed disproportionation reaction of an aldehyde, ...
A tandem Cu-catalyzed oxidation-intramolecular Cannizzaro reaction leading to bioactive α-hydroxyesters from α-hydroxyketones is reported.The process uses oxygen as a sole oxidant to achieve the formation of glyoxals, which are efficiently converted in situ to important α-hydroxyesters.The mechanistic insights are provided by isotopic labeling and supported by DFT calculations.
Several aldehydes undergo disproportionation into corresponding acids and alcohols (Cannizzaro reaction) over calcined hydrotalcite, magnesium aluminum layered double hydroxide (LDH), in water. The reactions are slow and ~10% conversions were achieved after stirring for 24 h at room temperature. The mixed metal oxide obtained on calcination of the LDH gets hydrated to a meixnerite-type phase ...
The reaction in which the oxidant aldehyde differs from the reductant aldehyde is referred to as the cross (or crossed) Cannizzaro reaction, which is quite useful for synthesizing a high yield of alcohol. The aldehydes are arranged in order of diminishing susceptibility to oxidation: m ‐nitrobenzaldehyde, furfural, p ‐bromobenzaldehyde ...
Aldehydes used in microwave-assisted Cannizzaro reaction. Optimisation of process condition for furfural aldehyde (1a). a. The effect of paraformaldehyde (1k) addition to Cannizzaro reaction of ...
Studies on the Mechanism of the Cannizzaro Reaction. II. Hydroxy and Amino Aldehyde Derivatives. Elliot R. Alexander; Cite this: J. Am. Chem. Soc. 1948, 70, 7, 2592-2594. ... The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at ...
An ultimate technique for disqualifying compounds suspected of being intermediates is illustrated by the use of isotope dilution to prove that benzyl benzoate is not an intermediate in the Cannizzaro reaction of 0.5 M benzaldehyde-p-t (tritium labeled) with 0.25 M sodium hydroxide in 74% methanol to 26% water at 100/sup 0/C. The adduct from hydroxide ion and two molecules of benzaldehyde that ...
From the book Organic Chemistry: 100 Must-Know Mechanisms. 22 Cannizzaro Reaction was published in Organic Chemistry: 100 Must-Know Mechanisms on page 54.
The reaction in which two aldehyde groups are transformed into the corresponding hydroxyl and carbonyl functions, existing separately or in combination as an ester, has been termed the Cannizzaro reaction. Here the discussion is restricted to the dismutation of two similar aldehyde groups into the corresponding alcohol and carboxylic salt ...
A room-temperature convenient Cannizzaro reaction prompted by magnesium bromide ethyl etherate and triethylamine is described for smooth conversion of aromatic aldehydes into their respective alcohols and carboxylic acids. The methodology is applicable to both inter- and intramolecular reactions and could be directed to obtain the carboxylic moiety in the form of an acid, an amide, or an ester ...
The reaction in which two aldehyde groups are transformed into the corresponding hydroxyl and carbonyl functions, existing separately or in combination as an ester, has been termed the Cannizzaro reaction. Here the discussion is restricted to the dismutation of two similar aldehyde groups into the corresponding alcohol and carboxylic salt function by means of aqueous or alcoholic and alkali.
The Cannizzaro reaction is a base-promoted redox reaction producing a primary alcohol and a carboxylic acid from two molecules of a nonenolizable aldehyde. The reaction commences when the anionic counterpart of the base attacks the carbonyl carbon, resulting in a tetrahedral alkoxide intermediate. The base then abstracts a proton from the ...
A Novel Type of Cannizzaro Reaction. Edward M. Fry, E. Justin Wilson Jr., and ; C. S. Hudson; Cite this: J. Am. Chem. Soc. 1942, 64, 4, 872-873. Publication Date (Print): April 1, 1942. ... The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load ...