Question

Since you cannot make a primary carbocation with alkylation, how do you add alkyl chains onto the aromatic ring on the primary carbon?

Answer 1

Alkyl chains can be added onto the primary carbon of an aromatic ring using Electrophilic Aromatic Substitution (EAS) without forming primary carbocations by using catalysts like aluminum chloride to facilitate the reaction.

Step-by-step explanation:

To add alkyl chains onto the primary carbon of an aromatic ring when primary carbocations are not favorable, we generally use a reaction technique known as Electrophilic Aromatic Substitution (EAS). In EAS, a strong electrophile attacks the aromatic ring, forming a highly unstable intermediate. Aluminum chloride is often used as a catalyst to facilitate the alkylation of benzene with alkyl halides. For instance, in the reaction of benzene with chloroethane catalyzed by aluminum chloride, ethylbenzene is produced without the intermediate formation of a primary carbocation.