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Malonic Ester Synthesis
The malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon alpha (directly adjacent) to both carbonyl groups, and then converted to a substituted acetic acid. A major drawback of malonic ester synthesis is that the alkylation stage can also produce dialkylated structures. This makes separation of products difficult and yields lower. Mechanism The carbons alpha to carbonyl groups can be deprotonated by a strong base. The carbanion formed can undergo nucleophilic substitution on the alkyl halide, to give the alkylated compound. On heating, the di-ester undergoes thermal decarboxylation, yielding an acetic acid substituted by the appropriate R group. Thus, the malonic ester can be thought of being equivalent to the −CH2COOH synthon. The esters chosen are usually the same as the base used, i.e. ethyl esters with sodium ethoxide. This is to prevent scrambling by transesterification. Variations Dialky ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diethyl Malonate
Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B1, and vitamin B6. Structure and properties Malonic acid is a rather simple dicarboxylic acid, with two carboxyl groups close together. In forming diethyl malonate from malonic acid, the hydroxyl group (−OH) on both of the carboxyl groups is replaced by an ethoxy group (−OEt; −OCH2CH3). The methylene group (−CH2−) in the middle of the malonic part of the diethyl malonate molecule is neighboured by two carbonyl groups (−C(=O)−). The hydrogen atoms on the carbon adjacent to the carbonyl group in a molecule are significantly more acidic than hydrogen atoms on a carbon adjacent to alkyl groups (up to 30 orders of magnitude). (This is known as the α position wi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sodium Ethoxide
Sodium ethoxide, also referred to as sodium ethanolate, is the Ionic compound, ionic, organic compound with the formula , , or NaOEt (Et = ethyl group, ethyl). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol. It is commonly used as a strong Base (chemistry), base. Preparation Few procedures have been reported to prepare the anhydrous solid. Instead the material is typically prepared in a solution with ethanol. It is commercially available and as a solution in ethanol. It is easily prepared in the laboratory by treating sodium metal with absolute ethanol: : The reaction of sodium hydroxide with anhydrous ethanol suffers from incomplete conversion to the ethoxide, but can still produce dry NaOEt by precipitation using acetone, or by drying using additional NaOH. Structure The crystal structure of sodium ethoxide has been determined by X-ray crystallography. It consists of layers of alternating and centres with ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetoacetic Ester Synthesis
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Mechanism A strong base deprotonates the dicarbonyl α-carbon. This carbon is preferred over the methyl carbon because the formed enolate is conjugation (organic chemistry), conjugated and thus resonance stabilized. The carbon then undergoes nucleophilic substitution. When heated with aqueous acid, the newly alkylated ester is hydrolyzed to a β-keto acid, which is decarboxylated to form a methyl ketone. The alkylated ester can undergo a second substitution to produce the dialkylated product. Double deprotonation of ethyl acetoacetate The classical acetoacetatic ester synthesis utilizes the 1:1 conjugate base. Ethyl acetoacetate is however diprotic: :CH3C(O)CH2CO2Et + NaH → CH3C(O)CH(Na)CO2Et + H2 :CH3C(O)CH(Na)CO2 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Knoevenagel Condensation
In organic chemistry, the Knoevenagel condensation () reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation. A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule of water is eliminated (hence ''condensation''). The product is often an α,β-unsaturated ketone (a conjugated enone). In this reaction the carbonyl group is an aldehyde or a ketone. The catalyst is usually a weakly basic amine. The active hydrogen component has the forms: * or for instance diethyl malonate, Meldrum's acid, ethyl acetoacetate or malonic acid, or cyanoacetic acid. * , for instance nitromethane. where Z is an electron withdrawing group. Z must be powerful enough to facilitate deprotonation to the enolate ion even with a mild base. Using a strong base in this reaction would induce self-condensation of the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Barbiturate
Barbiturates are a class of depressant, depressant drugs that are chemically derived from barbituric acid. They are effective when used medication, medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as well as overdose potential among other possible adverse effects. They have been recreational drug use, used recreationally for their anti-anxiety and sedative effects, and are thus prohibition of drugs, controlled in most countries due to the risks associated with such use. Barbiturates have largely been replaced by benzodiazepines and nonbenzodiazepines ("Z-drugs") in routine medical practice, particularly in the treatment of anxiety disorders and insomnia, because of the significantly lower risk of overdose, and the lack of an antidote for barbiturate overdose. Despite this, barbiturates are still in use for various purposes: in general anesthesia, epilepsy, treatment of acute migraines or cluster headaches, acute t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Berichte Der Deutschen Chemischen Gesellschaft
''Chemische Berichte'' (usually abbreviated as ''Ber.'' or ''Chem. Ber.'') was a German-language scientific journal of all disciplines of chemistry founded in 1868. It was one of the oldest scientific journals in chemistry, until it merged with '' Recueil des Travaux Chimiques des Pays-Bas'' to form ''Chemische Berichte/Recueil'' in 1997. ''Chemische Berichte/Recueil'' was then merged with other European journals in 1998 to form '' European Journal of Inorganic Chemistry''. History Founded in 1868 as ''Berichte der Deutschen Chemischen Gesellschaft'' (, CODEN BDCGAS), it operated under this title until 1928 (Vol. 61). The journal was then split into: * ''Berichte der Deutschen Chemischen Gesellschaft, A: Vereins-Nachrichten'' (, CODEN BDCAAS), and * ''Berichte der Deutschen Chemischen Gesellschaft, B: Abhandlungen'' (, CODEN BDCBAD). Vol. 78 and 79 (1945–1946) were omitted and not published due to World War II. The journal was renamed ''Chemische Berichte'' (, CODEN CHBEAM) in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
William Henry Perkin, Jr
William is a masculine given name of Germanic origin. It became popular in England after the Norman conquest in 1066,All Things William"Meaning & Origin of the Name"/ref> and remained so throughout the Middle Ages and into the modern era. It is sometimes abbreviated "Wm." Shortened familiar versions in English include Will or Wil, Wills, Willy, Willie, Bill, Billie, and Billy. A common Irish form is Liam. Scottish diminutives include Wull, Willie or Wullie (as in Oor Wullie). Female forms include Willa, Willemina, Wilma and Wilhelmina. Etymology William is related to the German given name ''Wilhelm''. Both ultimately descend from Proto-Germanic ''*Wiljahelmaz'', with a direct cognate also in the Old Norse name ''Vilhjalmr'' and a West Germanic borrowing into Medieval Latin ''Willelmus''. The Proto-Germanic name is a compound of *''wiljô'' "will, wish, desire" and *''helmaz'' "helm, helmet".Hanks, Hardcastle and Hodges, ''Oxford Dictionary of First Names'', Oxford Unive ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alicyclic Compound
In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. Cycloalkanes The simplest alicyclic compounds are the monocyclic cycloalkanes: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and so on. Bicyclic alkanes include decalin, housane, and norbornane. Polycyclic alkanes include cubane, basketane, and tetrahedrane. Spiro compounds have two or more rings that are connected through only one carbon atom. The mode of ring-closing in the formation of many alicyclic compounds can be predicted by Baldwin's rules. Otto Wallach, a German chemist, received the 1910 Nobel Prize in Chemistry for his work on alicyclic compounds. Cycloalkenes Monocyclic cycloalkenes are cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, and so on. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Halide
In chemistry, a halide (rarely halogenide) is a binary chemical compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fluoride, chloride, bromide, iodide, astatide, or theoretically tennesside compound. The alkali metals combine directly with halogens under appropriate conditions forming halides of the general formula, MX (X = F, Cl, Br or I). Many salts are halides; the ''hal-'' syllable in ''halide'' and '' halite'' reflects this correlation. A halide ion is a halogen atom bearing a negative charge. The common halide anions are fluoride (), chloride (), bromide (), and iodide (). Such ions are present in many ionic halide salts. Halide minerals contain halides. All these halide anions are colorless. Halides also form covalent bonds, examples being colorless TiF4, colorless TiCl4, orange TiBr4, and brown TiI4. The heavier members TiCl4, TiBr4 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
