Chapter 15
α-Carbon Chemistry: Enols, Enolates, and Enamines
Reaktywność enoli
Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A ...
Reaktywność jonów enolanowych
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, ...
Rodzaje enoli i enolanów
Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is ...
Konwencje mechanizmu enolatu
When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an ...
Regioselektywne tworzenie enolanów
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, ...
Stereochemiczne efekty enolizacji
The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound ...
Katalizowana kwasem α-halogenowanie aldehydów i ketonów
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first ...
Wspomagane zasadą α-halogenowanie aldehydów i ketonów
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base. ...
Wielokrotne halogenowanie ketonów metylowych: reakcja haloformowa
A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with ...
α-halogenowanie pochodnych kwasów karboksylowych: przegląd
Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, ...
α-bromowanie kwasów karboksylowych: reakcja Hella-Volharda-Zelinskiego
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the ...
Reakcje związków α-halokarbonylowych: substytucja nukleofilowa
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out ...
Nitrozacja enoli
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in ...
Tworzenie wiązań C-C: przegląd kondensacji aldolowej
Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. ...
Katalizowana zasadą reakcja addycji aldoli
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy ...
Katalizowana kwasem reakcja addycji aldoli
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The ...
Odwodnienie aldoli do enali: kondensacja aldoli katalizowana zasadą
This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy ...
Odwodnienie aldoli do enonów: katalizowana kwasem kondensacja aldoli
As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.
Figure 1. ...
Wewnątrzcząsteczkowa reakcja aldolowa
Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more ...
Rozszczepienie wiązania C-C: reakcja retro-aldolowa
The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under ...
Skrzyżowane reakcje aldolowe: przegląd
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds ...
Krzyżowa reakcja aldolowa przy użyciu słabych zasad
This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it ...
Ketony z nieennolizowanymi aldehydami aromatycznymi: kondensacja Claisena-Schmidta
Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the ...
Krzyżowa reakcja aldolowa przy użyciu silnych zasad: ukierunkowana reakcja aldolowa
The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to ...
Kondensacja aldolowa z β-Diesters: Kondensacja Knoevenagel
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as ...
Estry do β-ketoestrów: przegląd kondensacji Claisen
Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It ...
Estry do β-ketoestrów: mechanizm kondensacji Claisena
Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the ...
Kondensacja aldolowa a kondensacja Claisena
Aldol condensation is an acid or base-catalyzed condensation between aldehydes or ketones to give an α,ꞵ-unsaturated carbonyl compound. A ...
Wewnątrzcząsteczkowa kondensacja estrów dikarboksylowych Claisena: cyklizacja Dieckmanna
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic ...
Związki β-dikarbonylowe poprzez skrzyżowane kondensacje Claisen
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction ...
α-alkilowanie ketonów za pomocą jonów enolanowych
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by ...
Czynniki wpływające na α-alkilowanie ketonów: wybór zasady
α-Alkylation of ketones is achieved in the presence of alkyl halides and a base. The reaction proceeds via the formation of an enolate ion followed ...
Alkilowanie enolatów β-ketoestrów: synteza estrów acetooctowych
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide ...
Alkilowanie enolanów β-diestrowych: synteza estrów malonowych
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
The ...
Sprzężona addycja do α,β-nienasyconych związków karbonylowych
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in ...
Dodawanie sprzężone (1,4-addycja) vs bezpośrednie dodawanie (1,2-dodawanie)
α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic ...
Sprzężone dodawanie enolatanów: dodawanie Michała
The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition ...
Cykloheksenony poprzez addycję Michaela i kondensację aldolową: unieważnienie Robinsona
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, ...
Synteza α podstawionych związków karbonylowych: reakcja bociana enamina
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines ...
Aldehydy nonenolizowane do kwasów i alkoholi: reakcja Cannizzaro
The Cannizzaro reaction is a base-promoted redox reaction producing a primary alcohol and a carboxylic acid from two molecules of a nonenolizable ...
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