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Draw the organic product(s) you would expect from the following reaction. Assume products derive from the most stable carbocation intermediate(s).
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⋅ You do not have to consider stereochemistry.
⋅ If there is more than one major product possible, draw all of them.
⋅ Draw one structure per sketcher. Add additional sketchers using the dropdown menu in the bottom right corner.
Carbocations possess a positive charge on carbon atoms. Certain carbocations are more durable than others. More hydrogen-atoms that are attached to carbons with a positive charge and the lower the stability of the carbocation. Another way to look at this is that the more carbon groups that are attached to the carbocation the more stable it will be.
In general, alkenes undergo an electrophilic adding reaction. These are when electrons from Pi bonds attack the electrophiles and form the most stable carbocation. A nucleophile is used to attack carbocation in electrophilic addition to create a product. Most electrophilic addition reactions result in Markovikov products, in which a nucleophile is added at the most substituted carbon.
An arrow pushing technique is used to depict the mechanism for electrophilic addition reaction.
The following steps are required to add a hydrogen halide to an Alkene:
Step 1: An electrophilic attack on a portion of HX at the p electrons in the alkene results is the formation of a carbocation as well as the halide Ion.
Step 2: The alkyl halide is formed by the nucleophilic attack on the halide-ion carbocation.
The intermediate (carbocation), formed during the hydrohalogenation reaction determines the structure of the product.
Below is the Carbocation stability ordering:
The secondary carbocation was attacked by the generated nucleophiles to form secondary alkyl chloride.
Rearrangement:
Now, the carbocation is being attacked by Chloride Ion (Cl–)
Below are the organic products of the reaction:
And