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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.
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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...
[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.
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

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Related Experiment Video

Updated: Jun 1, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

cis-Cyclo-heptane-1,2-diol.

Richard Betz1, Peter Klüfers, Peter Mayer

  • 1Ludwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13 (Haus D), 81377 München, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study characterizes cis-cycloheptane-1,2-diol, a vicinal diol. Its molecular structure and crystal packing reveal specific torsion angles and hydrogen bonding patterns, contributing to understanding cycloalkane diol conformations.

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

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Last Updated: Jun 1, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Cycloheptane derivatives are less studied than their five- and six-membered ring counterparts.
  • Vicinal diols are important functional groups in organic synthesis and biochemistry.
  • Understanding the conformational preferences of cycloalkane diols is crucial for predicting their reactivity and properties.

Purpose of the Study:

  • To determine the crystal structure and molecular conformation of cis-cycloheptane-1,2-diol.
  • To analyze the O-C-C-O torsion angles and compare them with related cyclic systems.
  • To investigate the intermolecular interactions, specifically hydrogen bonding, in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was used to elucidate the three-dimensional structure.
  • Analysis of crystallographic data included determination of molecular symmetry and torsion angles.
  • Identification and analysis of hydrogen bonding networks within the crystal lattice.

Main Results:

  • The crystal structure of cis-cycloheptane-1,2-diol (C(7)H(14)O(2)) was determined.
  • Molecules exhibit no non-crystallographic symmetry.
  • Observed O-C-C-O torsion angles are comparable to trans-cyclohexane derivatives and rac-trans-cycloheptane-1,2-diol, but smaller than in trans-cyclopentane derivatives.
  • The crystal structure features sheets formed by O-H⋯O hydrogen bonds parallel to the [110] plane.

Conclusions:

  • The conformational analysis provides insights into the preferred geometry of seven-membered rings with vicinal diol functionalities.
  • The hydrogen bonding network dictates the packing in the solid state, forming extended sheet structures.
  • This study contributes to the understanding of stereochemistry and intermolecular forces in cycloalkane diols.