Question

Upon reacting 1,4-di-t-butylbenzene with aluminum trichloride and t-butyl chloride, the main product formed is 1,3,5-tri-t-butylbenzene due...

Upon reacting 1,4-di-t-butylbenzene with aluminum trichloride and t-butyl chloride, the main product formed is 1,3,5-tri-t-butylbenzene due to the demand of the t-butyl group. What best explains this phenomenon? (Hint: This is still essentially a Freidel-Crafts reaction; think about the mechanism of alkylation.)

Homework Answers

Answer #1

Answer: According to question , Here you must have to know that friedel crafts alkylation is a reversible process.

Alkylating benzene with t-butylchloride will give you the 1,4 t-butyl product. However, further alkylating it will not give you the 1,2,4 t-butyl product as you might expect. What actually happens is a series of alkylations and dealkylations which ultimately lead to the most stable molecule, the 1,3,5 t-butyl product.

And Also the 1,3,5-tri-t-butylbenzene is more thermodynamically stable compounds and less hindered .

So , this is all about the given question i hope you understand it clearlly . Thank you :)

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