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Related Concept Videos

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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Related Experiment Video

Updated: Jun 2, 2026

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

Published on: June 21, 2017

2-[3-((Z)-2-{4-[Bis(2-chloro-eth-yl)amino]-phen-yl}ethen-yl)-5,5-dimethyl-cyclo-hex-2-en-1-yl-idene]propane-dinitrile

Li Liu, Ying Shao, Jie-Ping Shi

    Acta Crystallographica. Section E, Structure Reports Online
    |April 28, 2011
    PubMed
    Summary

    This study details the crystal structure of a highly conjugated compound, C(23)H(25)Cl(2)N(3). The compound exhibits near planarity, with specific groups deviating from the main plane and crystal packing influenced by intermolecular interactions.

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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

    Published on: July 28, 2022

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Highly conjugated systems often display unique electronic and optical characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(23)H(25)Cl(2)N(3).
    • To analyze the molecular geometry, including planarity and ring conformations.
    • To investigate the intermolecular interactions governing crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of bond lengths, bond angles, and torsion angles provided geometric details.
    • Intermolecular interactions such as C-H⋯Cl and C-H⋯π were identified.

    Main Results:

    • The title compound, C(23)H(25)Cl(2)N(3), is nearly planar with a mean deviation of 0.049 Å.
    • Deviations from planarity were observed in the isopropylidene and chloromethyl groups.
    • The cyclo-hexene ring adopted an envelope conformation.
    • Crystal packing is stabilized by C-H⋯Cl and C-H⋯π interactions.

    Conclusions:

    • The detailed crystal structure of C(23)H(25)Cl(2)N(3) has been determined.
    • The molecular geometry and conformation were characterized.
    • Intermolecular interactions play a significant role in the solid-state organization of this compound.