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Darzens Reaction
The Darzens reaction (also known as the Darzens condensation or glycidic ester condensation) is the chemical reaction of a ketone or aldehyde with an α- haloester in the presence of a base to form an α,β-epoxy ester, also called a "glycidic ester". This reaction was discovered by the organic chemist Auguste Georges Darzens in 1904. : Reaction mechanism The reaction process begins when a strong base is used to form a carbanion at the halogenated position. Because of the ester, this carbanion is a resonance-stabilized enolate, which makes it relatively easy to form. This nucleophilic structure attacks another carbonyl component, forming a new carbon–carbon bond. These first two steps are similar to a base-catalyzed aldol reaction. The oxygen anion in this aldol-like product then does an intramolecular SN2 attack on the formerly-nucleophilic halide-bearing position, displacing the halide to form an epoxide. This reaction sequence is thus a condensation reaction since there i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Auguste Georges Darzens
Auguste Georges Darzens (12 July 1867 in Moscow, Russia – 10 September 1954) was a Russian-born French organic chemist. Biography From 1886 he studied at the École Polytechnique in Paris under Louis Édouard Grimaux. In 1895 he received his agrégation in physics and in 1899 his medical doctorate. From 1913 to 1937, he was a professor of chemistry at the École Polytechnique. In the meantime, from 1897 to 1920, he served as director of a research laboratory at LT Piver, a perfumery outfit. In 1904, he discovered the Darzens reaction, a chemical reaction also known as the Darzens condensation and Darzens glycidic ester condensation.Darzens, G., Compt. Rend. 1904, 139, 1214 Other reactions named after him include the Darzens tetralin synthesis, Darzens halogenation and the Darzens synthesis of unsaturated ketones. His book, "''Initiation chimique''" (1909), was translated into English in 1913 and published with the title of "Chemistry". [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nucleophile
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. ''Nucleophilic'' describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic character and is often used to compare the affinity of atoms. Neutral nucleophilic reactions with solvents such as alcohols and water are named solvolysis. Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile becomes attracted to a full or partial positive charge, and nucleophilic addition. Nucleophilicity is closely related to basicity. History The terms ''nucleophile'' and ''electrophile'' were introduced by Christopher Kelk Ingold in 1933, replacing the terms ''anionoid'' and ''cationoid' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stereochemistry
Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which by definition have the same molecular formula and sequence of bonded atoms (constitution), but differ in structural formula (the three-dimensional orientations of their atoms in space). For this reason, it is also known as 3D chemistry—the prefix "stereo-" means "three-dimensionality". Stereochemistry spans the entire spectrum of organic, inorganic, biological, physical and especially supramolecular chemistry. Stereochemistry includes methods for determining and describing these relationships; the effect on the physical or biological properties these relationships impart upon the molecules in question, and the manner in which these relationships influence the reactivity of the molecules in question ( dynamic stereochemis ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Side Reaction
A side reaction is a chemical reaction that occurs at the same time as the actual main reaction, but to a lesser extent. It leads to the formation of by-product, so that the yield of main product is reduced: : + B ->[] P1 : + C ->[] P2 P1 is the main product if k1> k2. The by-product P2 is generally undesirable and must be Separation process, separated from the actual main product (usually in a Industrial separation processes, costly process). In organic synthesis B and C from the above equations usually represent different compounds. However, they could also just be different positions in the same molecule. A side reaction is also referred to as competing reaction when different compounds (B, C) compete for another reactant (A). If the side reaction occurs about as often as the main reaction, it is spoken of parallel reactions (especially in the kinetics, see below). Also there may be more complicated relationships: Compound A could reversibly but quickly react to substan ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acyl
In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an alkyl group (). In organic chemistry, the acyl group (IUPAC name: alkanoyl) is usually derived from a carboxylic acid, in which case it has the formula , where R represents an alkyl group that is linked to the carbon atom of the group by a single bond. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond. Compounds Well-known acyl compounds are the acyl chlorides, such as acetyl chloride (CH3COCl) and benzoyl chloride (C6H5COCl). These compounds, which are treated as sources of acylium cations, are good reagents for attac ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkoxide
In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organic substituent. Alkoxides are strong bases and, when R is not bulky, good nucleophiles and good ligands. Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis. Transition metal alkoxides are widely used for coatings and as catalysts. Enolates are unsaturated alkoxides derived by deprotonation of a bond adjacent to a ketone or aldehyde. The nucleophilic center for simple alkoxides is located on the oxygen, whereas the nucleophilic site on enolates is delocalized onto both carbon and oxygen sites. Ynolates are also unsaturated alkoxides derived from acetylenic alcohols. Phenoxides are close relatives of the alkoxides, in which the alkyl group is replaced by a derivative of be ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Journal Of Organic Chemistry
''The Journal of Organic Chemistry'', colloquially known as ''JOC'', is a peer-reviewed scientific journal for original contributions of fundamental research in all branches of theory and practice in organic and bioorganic chemistry. It is published by the publishing arm of the American Chemical Society, with 24 issues per year. According to the ''Journal Citation Reports'', the journal had a 2017 impact factor of 4.805 and it is the journal that received the most cites (100,091 in 2017) in the field of organic chemistry. According to Web of Knowledge (and as December 2012), eleven papers from the journal have received more than 1,000 citations, with the most cited paper having received 7,967 citations. The current editor-in-chief is Scott J. Miller from Yale University. Indexing ''J. Org. Chem.'' is currently indexed in: See also *Organic Letters *Organometallics ''Organometallics'' is a biweekly journal published by the American Chemical Society. Its area of focus is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid () with the hydroxyl group () replaced by an amine group (); or, equivalently, an acyl (alkanoyl) group () joined to an amine group. Common examples of amides are acetamide (), benzamide (), and dimethylformamide (). Amides are qualified as primary, secondary, and tertiary according to whether the amine subgroup has the form , , or , where R and R' are groups other than hydrogen. The core of amides is called the amide group (specifically, carboxamide group). Amides are pervasive in nature and technology. Proteins and important plastics l ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Condensation Reaction
In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a dehydration synthesis. However other molecules can also be lost, such as ammonia, ethanol, acetic acid and hydrogen sulfide. The addition of the two molecules typically proceeds in a step-wise fashion to the addition product, usually in equilibrium, and with loss of a water molecule (hence the name condensation). The reaction may otherwise involve the functional groups of the molecule, and is a versatile class of reactions that can occur in acidic or basic conditions or in the presence of a catalyst. This class of reactions is a vital part of life as it is essential to the formation of peptide bonds between amino acids and to the biosynthesis of fatty acids. Many variations of condensation reactions exist. Common examples include the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
SN2 Reaction
The SN2 reaction is a type of reaction mechanism that is common in organic chemistry. In this mechanism, one bond is broken and one bond is formed in a concerted way, i.e., in one step. The name SN2 refers to the Hughes-Ingold symbol of the mechanism: "SN" indicates that the reaction is a nucleophilic substitution, and "2" that it proceeds via a bi-molecular mechanism, which means both the reacting species are involved in the rate-determining step. The other major type of nucleophilic substitution is the SN1, but many other more specialized mechanisms describe substitution reactions. The SN2 reaction can be considered as an analogue of the associative substitution in the field of inorganic chemistry. Reaction mechanism The reaction most often occurs at an aliphatic sp3 carbon center with an electronegative, stable leaving group attached to it (often denoted X), which is frequently a halide atom. The breaking of the C–X bond and the formation of the new bond (often deno ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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