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

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 β elimination or...
Radical Formation: Elimination00:51

Radical Formation: Elimination

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 to...
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

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 in the...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
E2 Reaction: Stereochemistry and Regiochemistry02:43

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...

You might also read

Related Articles

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

Sort by
Same author

First Evidence for Ozonido-TMC Complexes of Iron and Cobalt.

Angewandte Chemie (International ed. in English)·2026
Same author

The Sulfur Monoxide-Water Complex.

Journal of the American Chemical Society·2026
Same author

Assessing Benzene Dimer Interactions in Solution With a Molecular Balance.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

London Dispersion Favors <i>Cis</i> Selectivity in the Johnson-Corey-Chaykovsky Epoxidation.

The Journal of organic chemistry·2026
Same author

Synthesis of an <i>o</i>-Benzoquinone Arsenic Mononitride (As≡N) Complex and Its Reaction to Singlet Arsinonitrene.

Journal of the American Chemical Society·2026
Same author

Context Rules! Special Issue on "Physical Organic Chemistry: Never Out of Style".

The Journal of organic chemistry·2026

Related Experiment Video

Updated: May 30, 2026

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
09:08

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

Heuristic chemistry--elimination reactions.

Nicole Graulich1, Henning Hopf, Peter R Schreiner

  • 1Justus-Liebig-Universität Giessen, Institute für Organische Chemie, Heinrich-Buff-Ring 58, 35390 Giessen, Germany.

Chemistry, an Asian Journal
|August 2, 2011
PubMed
Summary

This study explores 1,x-elimination reactions beyond typical 1,2-eliminations in organic synthesis. It introduces mnemonic categories to simplify and rationalize diverse elimination reaction patterns and outcomes.

More Related Videos

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Related Experiment Videos

Last Updated: May 30, 2026

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
09:08

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Elimination reactions are crucial in organic synthesis, alongside addition and substitution reactions.
  • Existing reviews often focus on 1,2-eliminations, neglecting broader 1,x-elimination patterns.

Purpose of the Study:

  • To provide a conceptual review of 1,x-elimination reactions.
  • To expand the understanding of elimination chemistry beyond common olefin formation.
  • To develop a systematic approach for rationalizing various elimination reaction patterns.

Main Methods:

  • A heuristic approach was employed to analyze elimination reactions.
  • Recurrent reaction patterns were deduced from both traditional and specific elimination examples.
  • Mnemonic categories were developed for classification and understanding.

Main Results:

  • Identified and categorized diverse 1,x-elimination reaction patterns.
  • Demonstrated that 1,x-eliminations can be systematically understood.
  • Established a framework for rationalizing the outcomes of these reactions.

Conclusions:

  • 1,x-elimination reactions are more varied than commonly reviewed.
  • The proposed mnemonic categories offer a simplified way to understand these reactions.
  • This work provides a valuable tool for synthetic chemists to predict and utilize 1,x-eliminations.