3 edition of The mechanism of the condensation of indene with acetone and side reactions. found in the catalog.
The mechanism of the condensation of indene with acetone and side reactions.
Per Erik Ahlberg
Bibliography: p. 342.
|Series||Arkiv för kemi,, bd. 29, nr. 26|
|LC Classifications||QD1 .S923 bd. 29, nr. 26|
|The Physical Object|
|Number of Pages||342|
|LC Control Number||73392120|
ABSTRACT: Although aldol condensation is one of the most important organic reactions, capable of forming new C−C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones, is the ﬁnal loss of hydroxide and. Per Ahlberg has written: 'The mechanism of the condensation of indene with acetone and side reactions' -- subject(s): Acetone, Condensation products (Chemistry), Indenes, Rearrangements (Chemistry).
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Self-condensation is an organic reaction in which a chemical compound containing a carbonyl group acts both as the electrophile and the nucleophile in an aldol is also called a symmetrical aldol condensation as opposed to a mixed aldol condensation in which the electrophile and nucleophile are different species.
For example, two molecules of acetone condense to a single. However, mesityl oxide is formed when acetone is treated with dry HCl due to subsequent dehydration of initially formed diacetone alcohol.
The mesityl oxide may further condense with another molecule of acetone to give phorone. 2) An intra-molecular version of aldol condensation is. Aldol condensations are important in organic synthesis, because they provide a good way to form carbon–carbon bonds.
For example, the Robinson annulation reaction sequence features an aldol condensation; the Wieland–Miescher ketone product is an important starting material for many organic syntheses.
Aldol condensations are also commonly discussed in university level organic chemistry Organic Chemistry Portal: aldol-condensation. Use this lesson to learn about aldol condensation, a very interesting organic chemistry reaction. Read about the purpose of an aldol condensation and understand its mechanism and reaction.
The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone. It is named after Rainer Ludwig Claisen, Organic Chemistry Portal: claisen-condensation.
The products of these reactions are β-hydroxyaldehydes or aldehyde-alcohols = aldols. The simplest aldol reaction is the condensation of ethanal.
This is shown below in 2 different representations (the line diagrams are less cluttered). Crossed Claisen reactions are very important in biological processes.
The first step of the citric acid cycle is an enzyme catalyzed condensation of acetyl-CoA, a thioester, with oxaloacetate. The amino acid side chains in the active site hold the substrate molecules in place through hydrogen bonding.9File Size: KB.
Cyclization of electron-rich 2-alkylethynylbenzene derivatives was catalyzed by TpRuPPh 3 (CH 3 CN) 2 PF 6 in hot toluene to form 1-substituted-1H-indene and 1-indanone products.
The cyclization mechanism involves a 1,5-hydrogen shift of an initial metal-vinylidene intermediate. Odedra, S. Datta, R.-S. Liu, J. Org. Chem.,72, Condensations The Aldol Condensation. (Condensation reaction between 2 aldehydes or ketones) Mechanism under basic conditions. Can form the β-hydroxy carbonyl or the αβ-unsaturated carbonyl.
H O H O H H O H O H O O HOH H OH O H OH O H OH O H O HOOH-heat Mechanism under acidic conditions. Will probably eliminate to form the αβ File Size: 36KB. Step 1 is a Claisen ester condensation with loss of ethoxide from the ester acting as the carbonyl part.
The product is the $\beta$-ketoester (2). Upon acidification and heating, the ester is cleaved, the resulting $\beta$-ketoacid decarboxylates to yield the symmetrical ketone. 1) 4-hydroxymethylpentanone forms when acetone reacts with itself (does not spontaneously dehydrate to form a,b-unsat ketone because it is not conjugated) a.
NOTE: this product is less likely to form because ketones are less reactive than aldehydes. Condensation reaction: A reaction in which two or more molecules combine to form a larger molecule, with the simultaneous loss of a small molecule such as water or this occurs in many reactions, the term is usually reserved for reactions in which a new carbon-carbon bond is formed.
The Aldol Condensation This part of the mechanism is just like the mechanism for the addition reactions of Chapter In this example the enolate anion can be derived only from acetone. The electrophile is the more reactive carbonyl carbon, that of Size: KB.
Mechanism, references and reaction samples of the Claisen Condensation. The selectivity for the indenes is much higher than that starting from acetone with benzaldehyde, which shows that the aldol condensation product is an intermediate species to indene.
As Table 2 shows, butanone and 2-pentanone afforded 2-methylmethyleneindene (2a) and 2-ethylmethyleneindene (2b) with their hydrogenation products Cited by: Aldol reaction is an important organic reaction of aldehydes and ketones.
This reaction is shown by aldehydes and Ketones having alpha-hydrogen atom in the compound. Such a. A crossed aldol condensation uses two different aldehyde and/or ketone reactants.
Such reactions usually give a mixture of multiple condensation products, because there are two or more possible enolate nucleophiles, and two different carbonyl electrophiles.
In this crossed aldol condensation reaction example, four condensation products are. MECHANISM OF REACTION ALDOL CONDENSATION: An aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β‐ hydroxyaldehyde or β‐hydroxyketone, followed by a dehydration to give a conjugat.
The solid base catalysed aldol condensation of acetone was performed over a CsOH/SiO 2 catalyst using a H 2 carrier gas. The products observed were diacetone alcohol, mesityl oxide, phorone, iso-phorone and the hydrogenated product of mesityl oxide, methyl isobutyl ium tracer experiments were performed to gain an insight into the reaction by: The condensation portion of an aldol condensation reaction proceeds through an E2 mechanism false The driving force for the aldol condensation you performed was the thermodynamic stability gained from making a conjugated carbon-carbon double bond.
The condensation reaction of acetone, (CH3)2CO (propanone), in aqueous. solution is catalyzed by bases, B, which react reversibly with acetone to form the carbanion C3H5O. The carbanion then reacts with a molecule of acetone to give the product. The reaction of carbonyl compound enolates with aldehydes and ketones to form a β-hydroxy carbonyl compound is the Aldol Reaction, if conditions result in a subsequent dehydration to form the α,β-unsaturated compound, then the reaction is termed the Aldol Condensation (loss of a molecule of water).
A Double Aldol Condensation The Synthesis Of Dibenzalacetone H O O O 2 + NaOH Procedure: 1. In a 10xmm reaction tube, place 2 ml of 3 M NaOH solution, g of benzaldehyde (you might want to find the density of the benzaldehyde as it is easier to measure volumes of this liquid then mass) and ml of a % solution of acetone in File Size: 10KB.
The Knoevenagel condensation is an organic reaction used to convert an aldehyde or ketone and an activated methylene to a substituted olefin using an amine base as a catalyst. The reaction begins by deprotonation of the activated methylene by the base to give a resonance stabilized enolate.
1) The main mechanistic steps of the aldol condensation are shown in figures Using this information, propose a complete electron pushing mechanism for the formation of dibenzalacetone from acetone and benzaldehyde.
2) Figure 5 describes the formation of 4 different aldol condensation products. Draw theFile Size: KB. Crossed Claisen condensation is a variation of Claisen condensation. Claisen Condensation: Crossed Claisen Condensation: eg: mechanism: Step 1: The alkoxide ion deprotanates the enolizable ester reversibly.
Step 2 and 3: Enolate ion 1 undergoes a nucleophilic acyl substitution preferentially with the non-enolizable ester, which has the sterically less hindered and, therefore, more accessible.
I've provided diagrams for the self-condensation of acetaldehyde, however you should be able to draw an analogous mechanism for the self-condensation of butanal (your aldehyde).
Your mechanism is essentially correct, except for the final elimination step, which as you've drawn it gives the wrong product. Enolisation of the aldehyde.
Benzaldehyde, whose formula is (C 6 H 5 CHO), does not undergo aldol condensation, because it lacks alpha-hydrogen within its structure. This alpha-hydrogen is the hydrogen attached or adjacent to the carbon in the carbonyl group. Aldol condensation is a reaction between an aldehyde or a ketone and an enolate that subsequently leads to the formation of a new carbon-carbon double bond that.
Hydrolysis reactions: acid-catalyzed and saponification/base hydrolysis Chapter 14 – Amino Acids and Proteins Structure and parts of amino acids, classes of side chains D vs. L amino acids Amide-forming reactions of amino acids Drawing and naming and peptides (Ser-Lys-Ala) Structure of amino acids at different pH conditionsFile Size: 83KB.
Per Ahlberg has written: 'The mechanism of the condensation of indene with acetone and side reactions' -- subject(s): Acetone, Condensation products (Chemistry), Indenes, Rearrangements (Chemistry. Any aldehyde or ketone which contain at least one Alpha hydrogen, in the presence of base (Dil.) or acid undergoes condensation reaction and gives beta hydroxy aldehyde or ketone.
This condensation reaction is known as aldol condensation. Base may. The name aldol condensation is also commonly used, especially in biochemistry, to refer to the aldol reaction itself, as catalyzed r, the aldol reaction is not formally a condensation reaction because it does not involve the loss of a small molecule.
The reactions between a ketone and an aldehyde (crossed aldol condensation) or between two aldehydes also go by the /5(6). an aldol condensation.
Aldol condensation can be catalyzed by acids, but more we are using basic catalysis. Fig. 1 shows a reaction scheme for base-catalyzed aldol condensation, which involves the formation of an enolate (equilibrium reaction).
In the next step, the resulting enolate adds to the carbonyl group of the second Size: KB. The Knoevenagel condensation is a key step in the commercial production of the antimalarial drug lumefantrine (a component of Coartem): The initial reaction product is a mixture of E and Z isomers but because both isomers equilibrate rapidly around their common hydroxyl precursor, the more stable Z-isomer can eventually be c Chemistry Portal: knoevenagel-condensation.
Intramolecular Aldol condensations happen when a single molecule contains 2 reaction aldehyde/ketone groups. When the alpha carbon of one group attacks the other, the molecule attacks itself forming a.
Mechanism, references and reaction samples of the Knoevenagel Condensation. Crossed aldol reactions are possible with weak bases such as hydroxide or an alkoxide when one carbonyl reactant does not have an a hydrogen.
A reactant without a hydrogens cannot self-condense because it cannot form an enolate. We avoid self-condensation of File Size: KB. However, previously both the Knoevenagel reaction  and synthesis of coumarin by the Knoevenagel condensation  have been the subject of microwave induced reactions, in the case of coumarins the only example that has been always given is the synthesis of 3-ethoxycarbonylcoumarin (i.e., ethyl 2Hbenzopyranoxocarboxylate).
Aldol reactions are useful in organic chemistry synthesis for creating new carbon to carbon bonds. This reaction can occur as an aldol addition reaction at lower temperatures forming a beta-hydroxy aldehyde or ketone, or as an aldol condensation reaction at higher temperatures forming an alpha-beta unsaturated product.
The crossed-aldol condensation of 4-hydroxybenzaldehyde with acetone gives an adduct (4-(4-hydroxyphenyl)butenone), which is hydrogenated cleanly over.
Due to the relatively high acidity of the CH-acidic compounds applied in the Knoevenagel condensation, only a relatively weak base, such as an amine or KOH, is required.
Much like in aldol reactions, the addition of the carbanion to the carbonyl compound is frequently followed by dehydration.Chapter 17 25 Regioselective Formation of Enolate Anions Unsymmetrical ketones can form two different enolates The thermodynamic enolate is the most stable enolate i.e.
the one with the more highly substituted double bond A weak base favors the thermodynamic enolate because an equilibrium between the enolates is estabilished The kinetic enolate is the enolate formed fastest and it usually isFile Size: KB.Acylation of Ketones Reaction type: Nucleophilic Acyl Substitution.
Summary. Ketone enolates can be acylated with non-enolisable esters (i.e. an ester that lacks a-hydrogens).; Reagents: most commonly the base would be the alkoxide, RO- matching the alcohol portion of the ester (Remember enolates are good nucleophiles and the ester carbonyl C are electrophilic, and undergo nucleophilic.