Predict the products (if any) of the following reactions.
(b) (ex...

Question

Predict the products (if any) of the following reactions. (b) (excess) toluene + butan-1-ol + BF3

Accepted Answer

All right. Hi everyone. So for this question it says that we must predict the products of the following electra filic aromatic substitution reaction. And in this case we have a benzene ring with a church group attached and we have isopropyl alcohol. And we're reacting both of these things with um boron try fluoride. So let's get started with our reaction. And because we have um an alcohol group and an alcohol instead of a halogen, recall that this is going to be a variation of Friedel crafts um occupation. So this is free to craft calculation. I really hope I spelled the name correctly. But anyways, this is free to craft occupation. And the question then becomes on which position is our isopropyl group going to be added to our benzene ring Because recall that in a free to craft calculation, the hydrogen or the proton of an aromatic system is going to be replaced by that group. So our church butoh group on our benzene right here is what we call an activating group. It is an activating group because it's not very electro negative. Right? So that all kill group is going to donate electrons towards the aromatic system. And because it's an activating group, it is what we call Ortho slash para directing. It is or so Ortho sorry slash para directing. And just to recap, right, if you recall that if our tribunal group here is attached to carbon one, the Ortho position corresponds to carbon too. The para position is going to correspond to carbon three. Our para position is going to correspond to carbon four. So we have Ortho on two meta on three, and para on four. So if this church bugle group is activating that are isopropyl group should be either on carbon two or carbon four. So normally for this reaction, you would actually have a mixture of two products, right? You would have your Ortho and your parent product. But notice how both your church bugle group and your isopropyl group are relatively bulky, right there, relatively big. So the Ortho position would have way too much of hysteric hindrance for that product to be favored. So what's going to happen is that your product is going to be almost exclusively? Um, Para, Right? Both groups are going to be opposite of each other as a means of reducing that Starik hindrance. So in this case you would only see one product and that's going to be in the para position because there would be less Starik hindrance. So that's pretty much it. Thanks for watching. And I hope you found this helpful

Predict the products (if any) of the following reactions. (b) (excess) toluene + butan-1-ol + BF3

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