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

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

14.7K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
14.7K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.8K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.8K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

13.9K
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....
13.9K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.4K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.4K
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

4.0K
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
4.0K
Preparation of Alcohols via Substitution Reactions01:38

Preparation of Alcohols via Substitution Reactions

7.2K
Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group.  The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2,  depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
7.2K

You might also read

Related Articles

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

Sort by
Same author

Covalency control of photomagnetic relaxation in a manganese(II) photoswitch.

Nature chemistry·2026
Same author

1-(2,2-Di-phenyl-ethen-1-yl)tropylium perchlorate.

IUCrData·2026
Same author

20-Oxa-penta-cyclo-[15.2.1.0<sup>2,16</sup>.0<sup>3,8</sup>.0<sup>10,15</sup>]icosa-2(16),3,5,7,10(15),11,13,18-octaen-9-one.

IUCrData·2026
Same author

How to Handle Hard-to-Purify Polymers: Ammonium Sulfate Precipitation of rPEG as a Prototype for Amorphous and Flexible Polymers.

ACS macro letters·2026
Same author

<i>rac</i>-4<i>H</i>,5<i>H</i>,6<i>H</i>,7<i>H</i>,8<i>H</i>,9<i>H</i>,10<i>H</i>,11<i>H</i>-Cyclo-deca-[<i>d</i>][1,2,3]selena-diazol-4-ol.

IUCrData·2026
Same author

5-{4-[(1<i>R</i>,3<i>S</i>,4<i>S</i>)-Neomenth-yloxy]phen-yl}-1<i>H</i>-tetra-zole.

IUCrData·2026

Related Experiment Video

Updated: Jan 11, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.4K

(1R*,2R*,5R*,6S*)-6-Bromo-9-oxabi-cyclo-[3.3.1]nonan-2-ol.

Lea Simon1, Heiner Detert1, Dieter Schollmeyer1

  • 1University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.

Iucrdata
|November 12, 2025
PubMed
Summary

This study reveals that the bicyclo-[3.3.1] system adopts a chair conformation. Molecules form zigzag chains via hydrogen bonds, creating single-enantiomer crystal structures along the b-axis.

Keywords:
brominecrystal structureheterocyclehydrogen bridge

More Related Videos

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.2K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.6K

Related Experiment Videos

Last Updated: Jan 11, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.4K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.2K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.6K

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Bicyclo-[3.3.1] systems are prevalent in organic chemistry.
  • Understanding molecular conformation and intermolecular interactions is key to crystal engineering.

Purpose of the Study:

  • To elucidate the conformational preferences of a specific bicyclo-[3.3.1] system (C8H13BrO2).
  • To investigate the role of hydrogen bonding in the self-assembly of these molecules.
  • To characterize the resulting crystal structure and chain formation.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Conformational analysis of the bicyclo-[3.3.1] core.
  • Identification and analysis of intermolecular hydrogen bonding networks.

Main Results:

  • Both six-membered rings within the bicyclo-[3.3.1] system adopt a chair conformation.
  • Intramolecular hydrogen bonds between the hydroxy group and ether bridge link molecules into zigzag chains.
  • These chains form a crystal structure with single-enantiomer propagation along the b-axis.

Conclusions:

  • The chair conformation is favored in this bicyclo-[3.3.1] derivative.
  • Hydrogen bonding dictates the formation of one-dimensional supramolecular chains.
  • The study provides insights into crystal engineering of bicyclic compounds.