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E2 Reaction: Stereochemistry and Regiochemistry

E2 Reaction: Stereochemistry and Regiochemistry

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 product and...

Inductive Effects on Chemical Shift: Overview

Inductive Effects on Chemical Shift: Overview

The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...

E2 Reaction: Kinetics and Mechanism

E2 Reaction: Kinetics and Mechanism

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...

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

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...

Relative Stabilities of Alkenes

Relative Stabilities of Alkenes

The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene. The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.

E1 Reaction: Stereochemistry and Regiochemistry

E1 Reaction: Stereochemistry and Regiochemistry

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.

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Related Experiment Video

Updated: Jun 21, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

V₂O₅ Surface Electronic Structure Suppresses Ethane Over-Oxidation, Enabling 65% Ethylene Yield.

Hongjuan Tao¹, Yan Chen¹, Suting He¹

¹Guangdong Provincial Key Laboratory of Solid Wastes Pollution Control and Recycling, School of Environment and Energy, South China University of Technology, Guangzhou, China.

Angewandte Chemie (International Ed. in English)

|June 20, 2026

Summary

Engineered solid oxide electrolysis cells (SOECs) enhance ethane conversion to ethylene by modifying electrode surfaces. This approach improves selectivity and yield, overcoming limitations of traditional methods for energy-efficient chemical production.

Keywords:

anode modification impregnation oxidative dehydrogenation of ethane solid oxide electrolytic cell

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Last Updated: Jun 21, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

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Published on: August 17, 2019

Area of Science:

Electrochemistry
Materials Science
Catalysis

Background:

Electrochemical oxidative dehydrogenation (ODH) in solid oxide electrolysis cells (SOECs) is an energy-efficient pathway to ethylene production.
Over-oxidation leads to a trade-off between ethane conversion and ethylene selectivity.
Current regulation methods to mitigate over-oxidation often reduce ethane conversion.

Purpose of the Study:

To engineer the surface electronic structure of SOEC anodes for improved ethane ODH.
To investigate the synergistic effects of surface modification on ethane adsorption, dehydrogenation, and ethylene desorption.
To enhance ethylene yield and selectivity in ethane electro-oxidation.

Main Methods:

Deposition of a V2O5 layer on SrFe0.9Ti0.1O3-δ (STF) anode material.
Density functional theory (DFT) calculations to analyze electronic structure and reaction energetics.
Operando infrared spectroscopy to study reaction mechanisms.
Electrochemical performance testing at 750°C.

Main Results:

The V2O5-modified STF anode exhibited O 2p and V 3d states closer to the Fermi level.
Enhanced ethane adsorption (ΔEads: -0.33 vs. -0.11 eV) and promoted ethylene desorption were observed.
A reduced first dehydrogenation barrier (ΔG1: 1.13 vs. 1.15 eV) was determined.
The optimized anode achieved a 65% yield and 90% selectivity for ethylene, a 10% improvement over unmodified STF.

Conclusions:

Surface electronic structure engineering via V2O5 deposition effectively regulates ethane ODH reactions.
Band-center engineering is a viable strategy for optimizing hydrocarbon electrode reactions in SOECs.
The modified anode demonstrates superior performance in producing ethylene with high selectivity and conversion.