Rearrangement of benzilic acid
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This document summarizes the rearrangement of benzilic acid from benzil. It introduces benzilic acid and notes that it can be prepared through rearrangement of the 1,2-α-diketone benzil. The document then outlines the preparation of benzil, the rearrangement mechanism involving nucleophilic addition and migration, and properties of the resulting benzilic acid including its white crystalline structure and solubility in alcohols. Hazards of benzilic acid are also mentioned, noting it is very hazardous if in contact with skin or eyes or if ingested or inhaled, and that it is chemically stable under recommended storage conditions.
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Benzil benzilic acid rearrangement
Benzilic acid rearrangement. The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid.
Birch reduction
The Birch reduction is a reaction where aromatic compounds undergo partial reduction to unconjugated cyclohexadiene compounds in the presence of alkali metals like sodium or lithium in liquid ammonia. The solvated electrons from the reaction of the metal with liquid ammonia give the solution an intense blue color. The mechanism begins with single electron transfer from the metal to the aromatic ring, forming a radical anion. Regioselectivity in the reduction depends on whether substituents on the aromatic ring are electron donating groups or electron withdrawing groups. The Birch reduction can selectively reduce the less electron-rich ring in bicyclic aromatic compounds.
Hofman rearrangement
Hoffman Rearrangement is used to convert an unsubstituted amide into a primary amine with one carbon atom less than the amide.
2. LiAlH4
Lithium aluminium hydride (LAH) is a strong reducing agent that is commonly used to reduce carbonyl groups, esters, amides, nitriles, epoxides, lactones, and haloalkanes/haloarenes. LAH is prepared through the reaction of lithium hydride with aluminum chloride. It is a white solid that reacts violently with water, producing hydrogen gas, so reactions must be performed under anhydrous conditions. The mechanism of LAH involves nucleophilic hydride attack on the carbonyl carbon to form an intermediate tetrahedral structure.
Baeyer villiger oxidation
The Baeyer-Villiger oxidation reaction converts cyclic ketones to lactones and acyclic ketones to esters using a peroxy acid as the oxidizing agent. Adolf Baeyer and Victor Villiger first reported this reaction in 1899 using menthone and tetrahydrocarvone. The reaction involves the nucleophilic attack of the peroxy acid on the carbonyl carbon, followed by migration of an alkyl group to the oxygen and formation of the ester or lactone product. This reaction has been modified using hydrogen peroxide as the oxidant and various catalysts. It has applications in synthesizing pharmaceuticals, pheromones, and other fine chemicals.
SMILES REARRANGEMENT [REACTION AND MECHANISM]
The Smiles rearrangement is an intramolecular aromatic nucleophilic substitution reaction. It involves the migration of a substituent X from one carbon of an aromatic ring to another, with an aromatic substituent Y acting as the nucleophile. A specific example provided is the migration of an SO2Ar group to the ortho position of an ArO- nucleophile, activated by an adjacent nitro group. The X group is usually S, SO, or SO2, while the Y nucleophile is typically the conjugate base of OH, NH2, NHR or SH, though even CH2 has been used.
Seminar on name reaction
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Indole is an aromatic heterocyclic organic compound. It contains a benzene ring fused to a pyrrole ring. Indole occurs naturally in human feces and has an intense fecal odor. It is also found in coal tar and contributes to the scents of many flowers. Electrophilic aromatic substitution of indole occurs preferentially on the five-membered pyrrole ring. Indole can be synthesized via Fischer indole synthesis or Leimgruber synthesis. It has several pharmaceutical and medical uses including for treating cancer, fibromyalgia, and schizophrenia.
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Benzil benzilic acid rearrangement
Benzilic acid rearrangement. The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid.
Birch reduction
The Birch reduction is a reaction where aromatic compounds undergo partial reduction to unconjugated cyclohexadiene compounds in the presence of alkali metals like sodium or lithium in liquid ammonia. The solvated electrons from the reaction of the metal with liquid ammonia give the solution an intense blue color. The mechanism begins with single electron transfer from the metal to the aromatic ring, forming a radical anion. Regioselectivity in the reduction depends on whether substituents on the aromatic ring are electron donating groups or electron withdrawing groups. The Birch reduction can selectively reduce the less electron-rich ring in bicyclic aromatic compounds.
Hofman rearrangement
Hoffman Rearrangement is used to convert an unsubstituted amide into a primary amine with one carbon atom less than the amide.
2. LiAlH4
Lithium aluminium hydride (LAH) is a strong reducing agent that is commonly used to reduce carbonyl groups, esters, amides, nitriles, epoxides, lactones, and haloalkanes/haloarenes. LAH is prepared through the reaction of lithium hydride with aluminum chloride. It is a white solid that reacts violently with water, producing hydrogen gas, so reactions must be performed under anhydrous conditions. The mechanism of LAH involves nucleophilic hydride attack on the carbonyl carbon to form an intermediate tetrahedral structure.
Baeyer villiger oxidation
The Baeyer-Villiger oxidation reaction converts cyclic ketones to lactones and acyclic ketones to esters using a peroxy acid as the oxidizing agent. Adolf Baeyer and Victor Villiger first reported this reaction in 1899 using menthone and tetrahydrocarvone. The reaction involves the nucleophilic attack of the peroxy acid on the carbonyl carbon, followed by migration of an alkyl group to the oxygen and formation of the ester or lactone product. This reaction has been modified using hydrogen peroxide as the oxidant and various catalysts. It has applications in synthesizing pharmaceuticals, pheromones, and other fine chemicals.
SMILES REARRANGEMENT [REACTION AND MECHANISM]
The Smiles rearrangement is an intramolecular aromatic nucleophilic substitution reaction. It involves the migration of a substituent X from one carbon of an aromatic ring to another, with an aromatic substituent Y acting as the nucleophile. A specific example provided is the migration of an SO2Ar group to the ortho position of an ArO- nucleophile, activated by an adjacent nitro group. The X group is usually S, SO, or SO2, while the Y nucleophile is typically the conjugate base of OH, NH2, NHR or SH, though even CH2 has been used.
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Mannich reaction
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Ozonolysis
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Mannich reaction
The Mannich reaction involves the condensation of an enolizable carbonyl compound, an aldehyde such as formaldehyde, and an amine to form a β-amino carbonyl compound known as a Mannich base. The reaction proceeds via the initial addition of the amine to the aldehyde to form an iminium ion intermediate, which then reacts with the enol form of the carbonyl compound to eliminate a proton and form the Mannich base product. While versatile building blocks in organic synthesis, the Mannich reaction has limitations in terms of substrate scope and control of regio- and stereoselectivity. Examples of applications include the synthesis of tropinone, a precursor of atropine, as well
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Rearrangement of benzilic acid
- 1. Rearrangement of benzilic acid Prepared by: Aras jabar & shaxawan rahim university of silemany school of science chemistry department
- 2. Content: Introduction Preparation of benzil Rearrangement of benzilic acid Mechanism Migration IR spectrum Property of benzilic acid Hazardouse of benzilic acid
- 3. Introduction Benzilic acid will be prepared by causing a rearrangement of a α-diketone benzil The major condition of this rearrangement ,we must have 1,2-α-diketone
- 5. Rearrangement of benzilic acid
- 9. Rearrangement of nitro benzil
- 10. If we have cyclic compound
- 11. IR spectrum for benzil
- 12. IR spectrum for benzilic acid
- 13. Property of Product Benzilic acid is a white crystalline aromatic acid soluble in many primary alcohols. It can be prepared by heating mixture of benzil, alcohol and potassium hydroxide. The other preparation way is through benzaldehyde, which dimerizates to benzil and it is further transformed by benzilic acid rearrangement to benzilic acid.
- 14. application Doering extended the reaction to the formation of the corresponding ester by replacing the normal alkali by alkoxides. Thus benzil may directly be converted into alkyl benzilate by treatment with sodium alkoxide.
- 15. application The reaction may be used for the preparation of α-hydroxy acids from the easily accessible starting materials. It is important to note that as the ethoxide and isopropoxide ions reduce benzil to benzoin these reagents do not carry out benzilic rearrangement.
- 16. Hazardous of Benzilic Acid Potential Acute Health Effects: Very hazardous in case of skin contact (irritant), of eye contact (irritant). Hazardous in case of ingestion, of inhalation. Inflammation of the eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching. Chemical stability : Stable under recommended storage conditions. Hazardous combustion products : Under fire conditions, hazardous fumes will be present and product flammable at high temperature and product of combustion (CO,CO2).
- 17. Thank you