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Related Concept Videos

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...
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation01:14

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.
Types of Enols and Enolates01:19

Types of Enols and Enolates

Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional instability of enols...
Intramolecular Aldol Reaction01:18

Intramolecular Aldol Reaction

Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to those formed...
[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.
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.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

24-Methyl-enecyclo-artanone.

Hui-Ping Xiong, Zhi-Jun Wu, Fa-Tang Chen

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

    A novel tetra-cyclic triterpene, C(31)H(50)O, was isolated from Ainsliaea henryi. This molecule features a unique ring structure with specific conformational properties.

    Area of Science:

    • Natural Products Chemistry
    • Organic Chemistry
    • Phytochemistry

    Background:

    • Ainsliaea henryi is a plant species known for its potential chemical constituents.
    • Triterpenes are a class of organic compounds with diverse biological activities.

    Purpose of the Study:

    • To isolate and characterize a novel tetra-cyclic triterpene from Ainsliaea henryi.
    • To elucidate the structural features and conformational analysis of the isolated compound.

    Main Methods:

    • Isolation of the title compound using chromatographic techniques.
    • Structure elucidation employing spectroscopic methods (e.g., NMR, Mass Spectrometry).
    • Conformational analysis of the ring systems.

    Main Results:

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    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

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    Published on: June 13, 2022

    Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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    Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

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    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

    • Isolation and identification of a tetra-cyclic triterpene, C(31)H(50)O.
    • The molecule possesses a three-membered ring, a five-membered ring (envelope conformation), and three six-membered rings (chair conformations).

    Conclusions:

    • A new tetra-cyclic triterpene has been identified from Ainsliaea henryi.
    • The detailed structural and conformational analysis provides insights into the stereochemistry of this natural product.