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Basic Reactions in Organic Chemistry - Interactive

R. Ehrler, Germany, Contact: e-mail

Modelling Basic Organic Reactions by VRML 2.0 Techniques.

Playing the VRML 2.0 files requires a VRML PlugIn for example :


  • Energy function added
  • Bond types now visible: darker colors indicate stronger (double, triple) bonds
  • Animation starts by approximation - get closer to the molecules, using viewpoints, and the reaction will start
  • Now running best with Cortona VRML Client
  • Now compressed wrl-Files (very fast loading)

Awards:  Britannica Internet Guide


First Order Nucleophilic Substitution.

The nucleophilic substitution of a chlorine atom by a fluoride ion is described. The reaction is catalysed by a proton. 

A proton attacks the chlorine atom and forms hydrochloric acid. A tertiary carbon cation is formed as an intermediate (planar). From the right side hydrofluoric acid flies in. A proton is lost and t-butylfluoride is formed.


Second Order Nucleophilic Substitution.

The reaction of methylchloride with a fluoride ion is described. 

The fluoride ion (nucleophil) approaches from the right and substitutes the chloride ion in the molecule. A transition state is passed, where all 3 hydrogen atoms and the central carbon atom are arranged in a plane. Methylfluoride is formed. 


Second Order Nucleophilic Substitution with a Tetragonal Transition State

The reaction of acetylchloride with a methoxy ion is described. 

The methoxy ion (nucleophil) adds to the carbonyl group of the acetylchloride (tetragonal intermediate). The chloride ion will be lost, acetic acid methylester is formed. 



Second Order Vinylogous Nucleophilic Substitution.

The hydrolysis of allylchloride in water is described. 

A water molecule approaches the vinyl group of allylchloride at position 1 an substitutes the chloride ion at position 3. Hydrochloric acid is formed. The reaction product is allylic alcohol (propen-3-ol). 

Electrophilic Aromatic Substitution 

The nitration of phenol by a NO2 cation is described. 

The cation (linear) approaches at o-position of the phenole molecule and substitutes a hydrogen atom. The intermediate has a tetragonal structure. o-nitrophenole is the product. 



Pericyclic 4+2 Cycloaddition. 

The reaction of cyclohexadiene with maleic acid anhydride is described. A bicyclic ring system is formed. The reaction runs in concerted matter. 



Formation of styrene. 

The elimination of HCl promoted by a methoxide anion is described. Styrene is formed. First the chloroethylbenzene is deprotonated then the chloride-ion is lost. 



Addition of an alkylgroup (methyl) to ethylene at the active site of a Ziegler-type catalysator [TiCl4 AlH2CH3]. 



More??   See some basic stereochemical properties of organic molecules
VRML applications in chemistry from other authors:
    University of Aberystwyth
    Univeristy of Bristol
    University TH Darmstadt
All calculations are performed for gas phases. Solvent effect are not taken in consideration


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 Latest update:  2005-03-13 by Dr. Ehrler