Friedel Crafts Question

[FridelCrafts]

---

Members do not see this ad.

What's the product of the reaction between 1-methoxy-4-nitrobenzene and bromopentane with AlCl3?

I'm confused whether or not this reacts at all. First, wouldn't the nitro group deactivate the benzene enough for Friedel-Crafts to not occur?

Also can Friedel-Crafts work when attempting to attach a bromobutane to the 1-methoxy-4-nitrobenzene and using AlCl3 instead of AlBr3?

Thanks guys!

 

[BerkReviewTeach]

What's the product of the reaction between 1-methoxy-4-nitrobenzene and bromopentane with AlCl3?

I'm confused whether or not this reacts at all. First, wouldn't the nitro group deactivate the benzene enough for Friedel-Crafts to not occur?

Also can Friedel-Crafts work when attempting to attach a bromobutane to the 1-methoxy-4-nitrobenzene and using AlCl3 instead of AlBr3?

Thanks guys!

Luckily you don't need to worry about this reaction at all, as it is not tested on the MCAT. they removed it back in 2004, so you can completely omit it from your study plans.

 

[Gauss44]

Luckily you don't need to worry about this reaction at all, as it is not tested on the MCAT. they removed it back in 2004, so you can completely omit it from your study plans.

If a question involves Fridel Crafts/benzene/rings will it automatically be eliminated or potentially be eliminated? Because I heard that they kept the questions with Fridel Crafts/benzene/rings as long as those questions could be answered without specific knowledge of Fridel Crafts/benzene/rings, or in some other round-about way.

 

[BerkReviewTeach]

If a question involves Fridel Crafts/benzene/rings will it automatically be eliminated or potentially be eliminated? Because I heard that they kept the questions with Fridel Crafts/benzene/rings as long as those questions could be answered without specific knowledge of Fridel Crafts/benzene/rings, or in some other round-about way.

They officially removed reactions of benzene rings in 2004. In all of the time since then, had they asked something on EAS, I'm guessing someone would have complained that it was unfairly tested. Because no such complaint has shown up here, I'm reasoning that it has been completely eliminated as they said they'd do.

I believe that aromaticity and it's impact on electron density is still fair game, because it addresses structure and potentially addresses acidity and basicity. But in the case of predicting a product in a EAS reaction, which is what is being asked here, you can be sure it won't be on the MCAT.

About the only thing testable on the MCAT in the original question is that if it's 1-bromopentane, then there could be a good amount of rearrangement of the carbocation that forms. But all things considered, it is not only a non-MCAT question, it uses an incompatible Lewis acid for a bromoalkane and doesn't specify where the Br is found on the pentane chain.