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Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoWade 9th EditionCh. 22 - Condensations and Alpha Substitutions of Carbonyl CompoundsProblema 75d
Capitolo 22, Problema 75d

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.
(d)

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Step 1: Identify the product structure. The given compound contains a conjugated system with a C=C bond adjacent to a cyano group (-CN) and an ester group (-COOEt). This suggests it was formed via a Knoevenagel condensation reaction.
Step 2: Recall the general mechanism of Knoevenagel condensation. It involves the reaction of an aldehyde or ketone with an active methylene compound (a compound with acidic hydrogens between two electron-withdrawing groups).
Step 3: Analyze the product to deduce the active methylene compound. The presence of the cyano group (-CN) and ester group (-COOEt) indicates that the active methylene compound is ethyl cyanoacetate (EtOOC-CH2-CN).
Step 4: Determine the aldehyde or ketone used in the reaction. The aromatic ring with a single substituent (the conjugated C=C bond) suggests that benzaldehyde (C6H5CHO) was the aldehyde used.
Step 5: Combine the components. The Knoevenagel condensation between benzaldehyde (C6H5CHO) and ethyl cyanoacetate (EtOOC-CH2-CN) in the presence of a secondary amine catalyst would yield the given product.

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Knoevenagel Condensation

The Knoevenagel condensation is a reaction where an active methylene compound reacts with an aldehyde or ketone in the presence of a basic catalyst, typically a secondary amine. This reaction results in the formation of a carbon-carbon double bond (C=C) and is characterized by the elimination of a small molecule, often water. It is a key reaction in organic synthesis for forming α,β-unsaturated carbonyl compounds.
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Condensation Reactions

Active Methylene Compounds

Active methylene compounds are organic molecules that contain a methylene group (–CH2–) adjacent to a carbonyl group (C=O) or another electron-withdrawing group. This configuration makes the methylene hydrogen atoms particularly acidic, allowing them to be deprotonated to form a nucleophile that can attack electrophiles, such as aldehydes or ketones, in reactions like the Knoevenagel condensation.
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Defining meso compounds.

Aldol Condensation

Aldol condensation is a fundamental reaction in organic chemistry where aldehydes or ketones with α-hydrogens undergo a reaction to form β-hydroxy carbonyl compounds, which can further dehydrate to yield α,β-unsaturated carbonyl compounds. The Knoevenagel condensation can be viewed as a specific type of aldol condensation where the reaction involves an active methylene compound, highlighting the versatility of carbonyl chemistry in forming complex molecules.
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Crossed Aldol
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Domanda del libro di testo

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

(a)

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Domanda del libro di testo

Predict the products from this sequence of reactions.

1381
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Domanda del libro di testo

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

(c)

952
views
Domanda del libro di testo

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

(f)

601
views
Domanda del libro di testo

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

(e)

594
views
Domanda del libro di testo

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

(b)

1053
views