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Related Concept Videos

Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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.
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Related Experiment Video

Updated: Jun 1, 2026

Green Synthesis of Quinoline-Based Ionic Liquid
05:59

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

(+)-hexacyclinol.

David M Pinkerton1, Martin G Banwell, Anthony C Willis

  • 1Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

Enantioselective synthesis produced a complex organic molecule, C(23)H(28)O(7). Hydrogen bonding stabilizes the crystal structure, though absolute configuration requires further study.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Complex organic molecules are synthesized using enantioselective methods.
  • Crystal structure analysis provides insights into molecular interactions and stability.

Purpose of the Study:

  • To synthesize a specific title compound via enantioselective synthesis.
  • To analyze the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

  • Enantioselective synthesis of the title compound (C(23)H(28)O(7)).
  • X-ray crystallography to determine the crystal structure and asymmetric unit composition.
  • Analysis of hydrogen bonding interactions within the crystal lattice.

Main Results:

  • Successful enantioselective synthesis of the target molecule.
  • Identification of three molecules in the crystallographic asymmetric unit.
  • Observation of hydrogen bonding between hydroxyl and keto groups, contributing to structural stability.
  • The compound was enantiomerically pure, but absolute configuration was not directly determined.

Conclusions:

  • The synthesized compound is enantiomerically pure, stabilized by intermolecular hydrogen bonds.
  • The absolute configuration was inferred from the chiral precursor, highlighting the importance of synthetic route.
  • Further studies may be needed to definitively determine the absolute configuration.