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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Structure and Nomenclature of Ethers

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

E2 Reaction: Stereochemistry and Regiochemistry

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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...

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...

E1 Reaction: Kinetics and Mechanism

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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...

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Related Experiment Video

Updated: Jun 5, 2026

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

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(E)-1,2-Bis(3-bromo-4-methyl-phen-yl)ethene.

René T Boeré¹, Steven J Robbins

¹Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB, Canada T1K 3M4.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details the molecular structure of C(16)H(14)Br(2), revealing a central carbon-carbon double bond and near-planar benzene rings. These findings offer insights into the compound's structural characteristics and potential reactivity.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Dibrominated organic compounds often serve as intermediates in various synthetic pathways.

Purpose of the Study:

To elucidate the detailed crystal structure of the title compound, C(16)H(14)Br(2).
To quantify key bond lengths and angles, particularly around the central double bond and benzene rings.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular structure.
Crystallographic data were analyzed to obtain precise bond lengths and torsion angles.

Main Results:

The central carbon-carbon double bond (C=C) was measured at 1.329(4) Å.
The two benzene rings exhibit near-planarity with the double bond, showing twist angles of 7.5(2)° and 13.6(2)°.

Conclusions:

The determined structure of C(16)H(14)Br(2) provides a precise geometric description.
The near-planar conformation suggests potential for pi-electron delocalization and influences the molecule's overall electronic properties.