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Related Concept Videos

E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
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α-Alkylation of Ketones via Enolate Ions01:10

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

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Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the...
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Related Experiment Video

Updated: Jun 13, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Electrochemical allylations in a deep eutectic solvent.

Sophia Taylor1, Scott T Handy1

  • 1Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN, USA.

Beilstein Journal of Organic Chemistry
|September 17, 2024
PubMed
Summary
This summary is machine-generated.

Electrosynthesis using deep eutectic solvents offers a greener approach to carbonyl allylation. These solvents enable metal recovery, presenting a novel recycling strategy for electrochemical reactions.

Keywords:
allylationelectrosynthesiseutectic solventrecyclingtin

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Area of Science:

  • Green chemistry
  • Electrochemistry
  • Organic synthesis

Background:

  • Electrosynthesis is gaining traction due to its environmental benefits.
  • Electrosynthesis necessitates solvents and electrolytes, which are consumed unless recycled.
  • Deep eutectic solvents (DES) are explored as sustainable alternatives.

Purpose of the Study:

  • To investigate the use of recyclable deep eutectic solvents for the allylation of carbonyls.
  • To develop greener conditions for electrochemical allylation reactions.
  • To address the challenge of reagent consumption in electrosynthesis.

Main Methods:

  • Exploration of deep eutectic solvents for carbonyl allylation.
  • Development of various reaction conditions.
  • Investigation of metal recovery and recycling within the DES system.

Main Results:

  • Several reaction conditions for carbonyl allylation using DES were established.
  • The complete avoidance of stoichiometric metal reagents remained challenging.
  • Deep eutectic solvents demonstrated the ability to plate out and recover metals.

Conclusions:

  • Deep eutectic solvents show promise for sustainable electrosynthesis.
  • Metal recovery using DES provides a new avenue for electrochemical allylation.
  • Further research is needed to fully eliminate stoichiometric metal reagents.