EAS Reactions - how do you know which comes first?

[ballyhoo]

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Hi,

I'm doing the Destroyer for Ochem and still can't figure out why for number 19, the answer is D over A. Both are using the same reagents, and I understand what each step is for, but how do you know whether chlorination comes first or nitration comes first?

Thanks! 😀

 

[diene]

Hi,

I'm doing the Destroyer for Ochem and still can't figure out why for number 19, the answer is D over A. Both are using the same reagents, and I understand what each step is for, but how do you know whether chlorination comes first or nitration comes first?

Thanks! 😀

In this case, nitration comes first because in the product that the student wanted to synthesize, chloride is in the meta position..if you remember, halides are deactivating BUT ortho/para directors, while NO2 is a meta director. If you had wanted the ortho/para product, chlorination would have come first

Hope this helps!

 

[Saiph]

I do not have the problem, but it depends on what product you want (ortho, meta, para). Having a nitro group means anything added would be meta directed, and for chloro ortho or para.

 

[njdoc327]

i'm guessing you have a different version from me because number 19 is different in my book. i have the 2012 version but for those questions, you just have to go over your meta and ortho/para directors

 

[ballyhoo]

Ah that makes sense! I forgot that halides were ortho/para directing. Thanks so much!