Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Elimination Reactions02:25

Elimination Reactions

16.4K
A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
16.4K
Radical Formation: Elimination00:51

Radical Formation: Elimination

2.1K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect...
2.1K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

12.1K
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...
12.1K
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

13.7K
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:
13.7K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.0K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

17.4K
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...
17.4K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Dynamics of CO<sub>2</sub> activation by gas-phase transition metal ions: the importance of intersystem crossing.

Physical chemistry chemical physics : PCCP·2026
Same author

Dichography: two-frame ultrafast imaging from a single diffraction pattern.

Nature communications·2026
Same author

Double Rotational Rainbows in Collisions of Homonuclear Diatoms Stemming from Steric Charge Transfer.

Journal of the American Chemical Society·2026
Same author

Redox Chemistry and Photophysics of the <b>[V(dgpy)</b><sub><b>2</b></sub><b>]</b><sup><b>3+/2+</b></sup> Redox Pair.

Inorganic chemistry·2026
Same author

Full-dimensional potential energy surface for the H2 + N2 system and quantum scattering calculations of collision-induced rotational energy transfer.

The Journal of chemical physics·2026
Same author

Unveiling a flip-over retention mechanism in the gas-phase Cl<sup>-</sup> + (CH<sub>3</sub>)<sub>3</sub>CI S<sub>N</sub>2 reaction.

Nature communications·2026

Related Experiment Video

Updated: Jan 2, 2026

Inducible and Reversible Dominant-negative DN Protein Inhibition
08:35

Inducible and Reversible Dominant-negative DN Protein Inhibition

Published on: January 7, 2019

8.7K

Unexpected Indirect Dynamics in Base-Induced Elimination.

Jennifer Meyer1, Eduardo Carrascosa1, Tim Michaelsen1

  • 1Institut für Ionenphysik und Angewandte Physik , Universität Innsbruck , Technikerstrasse 25 , 6020 Innsbruck , Austria.

Journal of the American Chemical Society
|November 30, 2019
PubMed
Summary
This summary is machine-generated.

Investigating base-induced elimination (E2) and nucleophilic substitution (SN2) reactions, this study reveals distinct dynamic mechanisms. Unexpectedly, product ion kinetic energy distributions were independent of collision energy, challenging static predictions.

More Related Videos

Following the Dynamics of Structural Variants in Experimentally Evolved Populations
04:52

Following the Dynamics of Structural Variants in Experimentally Evolved Populations

Published on: February 3, 2023

1.3K
Inherent Dynamics Visualizer, an Interactive Application for Evaluating and Visualizing Outputs from a Gene Regulatory Network Inference Pipeline
10:44

Inherent Dynamics Visualizer, an Interactive Application for Evaluating and Visualizing Outputs from a Gene Regulatory Network Inference Pipeline

Published on: December 7, 2021

2.6K

Related Experiment Videos

Last Updated: Jan 2, 2026

Inducible and Reversible Dominant-negative DN Protein Inhibition
08:35

Inducible and Reversible Dominant-negative DN Protein Inhibition

Published on: January 7, 2019

8.7K
Following the Dynamics of Structural Variants in Experimentally Evolved Populations
04:52

Following the Dynamics of Structural Variants in Experimentally Evolved Populations

Published on: February 3, 2023

1.3K
Inherent Dynamics Visualizer, an Interactive Application for Evaluating and Visualizing Outputs from a Gene Regulatory Network Inference Pipeline
10:44

Inherent Dynamics Visualizer, an Interactive Application for Evaluating and Visualizing Outputs from a Gene Regulatory Network Inference Pipeline

Published on: December 7, 2021

2.6K

Area of Science:

  • Physical Chemistry
  • Chemical Dynamics
  • Reaction Mechanisms

Background:

  • Base-induced elimination (E2) and bimolecular nucleophilic substitution (SN2) are fundamental organic reactions.
  • These reactions compete, with anti-elimination often favored over syn-elimination.
  • Understanding intrinsic reaction dynamics requires single-collision condition studies.

Purpose of the Study:

  • To investigate the intrinsic dynamics of base-induced elimination reactions.
  • To explore the competition between E2 and SN2 reactions under single-collision conditions.
  • To analyze the reaction mechanisms of the fluoride anion with tert-butyl halides.

Main Methods:

  • Utilized reactive scattering experiments under single-collision conditions.
  • Focused on the prototype reaction system of fluoride anion and tert-butyl halides.
  • Analyzed mechanistic fingerprints, transition state energetics, and scattering signatures.

Main Results:

  • Steric hindrance at the alpha-carbon suppressed the SN2 pathway, favoring E2.
  • Energetically submerged anti-transition states were favored over syn-transition states.
  • Three distinct indirect dynamic mechanisms were identified across various collision energies.
  • Product ion kinetic energy distributions were unexpectedly independent of collision energy, attributed to dynamic trapping.

Conclusions:

  • Atomistic reaction dynamics cannot be solely predicted by stationary state arguments.
  • Dynamic trapping in a prereaction well, influenced by centrifugal potential, plays a significant role.
  • The study provides crucial insights into the complex interplay of factors governing E2 and SN2 reaction pathways.