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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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SN2 Reaction: Mechanism02:27

SN2 Reaction: Mechanism

14.6K
The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the nucleophile and the substrate participate in the rate-determining step.
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
14.6K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

10.5K
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...
10.5K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

15.6K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
15.6K
E1 Reaction: Stereochemistry and Regiochemistry02:43

E1 Reaction: Stereochemistry and Regiochemistry

9.8K
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.
9.8K
E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

11.8K
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
11.8K

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Electrochemical organic reactions: A tutorial review.

Joyeeta Lodh1, Shounik Paul1, He Sun2

  • 1Eco-Friendly Applied Materials Laboratory (EFAML), Materials Science Centre, Department of Chemical Sciences, Mohanpur Campus, Indian Institute of Science, Education and Research, Kolkata, West Bengal, India.

Frontiers in Chemistry
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This review explores optimizing electrochemical organic reactions by examining electrodes, electrolytes, and cell design. It highlights electrochemistry as a versatile synthetic tool, driven by physical organic chemistry principles.

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Area of Science:

  • Electrochemistry
  • Organic Chemistry
  • Physical Chemistry

Background:

  • Electrochemical reactions, while based on oxidation-reduction, present complexities in organic synthesis.
  • Principles of electrochemistry are rooted in physical organic chemistry, influencing various reaction types.
  • Recent advancements have expanded the utility of electrochemical methods in organic synthesis.

Purpose of the Study:

  • To review key factors influencing the optimization of electrochemical organic reactions.
  • To summarize significant studies in electrochemical organic synthesis over the past decade.
  • To underscore the versatility of electrochemistry as a synthetic tool.

Main Methods:

  • Discussion of critical parameters: electrode materials, supporting electrolytes, and electrochemical cell design.
  • Systematic review of published research in electrochemical organic synthesis from the last 10 years.
  • Analysis of how modifying constant electrolysis current impacts reaction outcomes.

Main Results:

  • Identification of crucial factors for optimizing electrochemical reactions, enabling predictable outcomes.
  • Compilation of a decade's worth of research, showcasing progress and trends.
  • Demonstration of electrochemistry's adaptability for synthetically valuable transformations.

Conclusions:

  • Electrochemical organic reactions can be effectively optimized through careful selection of reaction conditions.
  • The field has seen substantial growth, establishing electrochemistry as a powerful synthetic methodology.
  • Modulating electrolysis current offers a versatile approach to achieving desired synthetic outcomes.