Synthesize from benzene. (Hint: All of these require ...

Question

Synthesize from benzene. (Hint: All of these require diazonium ions.)

(d) 4-methoxyaniline

Accepted Answer

All right. Hi everyone. So for this question you must show how to synthesize the following compound from Benzie. And we have four with oxy aniline. And as a hint we are told that the synthesis requires dyas ammonium ions. So before I begin, let's recall really quickly that the Dia Sony um ion can be used as an intermediate for synthesizing a variety of groups in an aromatic system. Right. So we can go ahead and we can generate multiple groups using a Die Azzoni um intermediate. Which we can then take advantage of when synthesizing art athoc C group because our final product here is going to be for Toxie and alan, which um is gonna be a benzene ring with a primary amine attached and pere too. Um para to the primary amine here in our an allen we're going to have an epoxy group. So we're gonna have an oxygen Attached to two carbons attached to our Benzene Ring. So, like I mentioned before the Dia Sony um ion that the question mentions can be used as an intermediate for generating art with oxy group. So, let's go ahead and start with that. Right. So, if I draw benzene as my starting material here before I can introduce a di Azzoni um ion. Or rather make a dia sodium ion. I have to introduce nitrogen to the rape. Right. I have to introduce nitrogen to the system. And one common way we can do that recall is via nitrate in. Right? So if I react my benzene ring here with H. N. 03 in the presence of H two S. 04, that is going to install a nitro group but regardless. Right. Um We're still not ready for our Die Azzoni. Um Right, because recall that the dye Azzoni um um reaction is only with a primary aromatic amine. So that means we have to reduce our nitro group into a primary amine using um iron in the presence of Hcl. So instead of an N. 02, we're going to have an NH two which is therefore a primary aromatic amine that we can go ahead and um create our Die Azzoni. Um With so recall that Die Azzoni um can be made by reacting this primary aromatic amine with sodium nitrite in the presence of Hcl. So when you add those two, those three things together, you're going to replace your NH two With your n. two plus and chloride as a counter ion right stemming from your hcl. So now recall that I mentioned before that di Azzoni ums di ammonium ions are an important intermediate for generating several groups and one of these groups happens to be an age group. Right? So if you react your dyas ammonium ion with water in the presence of heat, you're going to install an O. H. Group where um where your di Azzoni um used to be. Right. So this is going to be our group, but this is not what we need necessarily. Right because we need an a foxy group. Not an O. H. But um what I want to bring to your attention is that if we go ahead And deep protein eight wrong color there. If we go ahead and deep protein eight are away troop with a strong base like sodium hydroxide, we can generate an O minus. Right? We can generate an an ion which can function as a strong a nuclear file. Right? So this nuclear file can react in a substitution reaction to add our ethyl group. Right? So if we react our nuclear file now our own minus with an ethyl hey line such as um iodide red, that's an ethyl hair light. Then our own minus is going to behave as a nuclear file and substitute itself with our iodine. Right? So iodine is going to get kicked out and our fo group is going to be associated to our oxygen instead. So this is going to be our oxygen. And now we are going to have our ethyl group attached. So now recall once again that with oxy groups and wilcox E groups in general are Ortho slash para directors. So now we can go ahead and install our primary amine to the para position relative to our epoxy group with relative ease. Right? So as we were talking about in the previous steps um a primary amine can be added to an aromatic ring by first installing a nitro group and then reducing it down to an amine. Right? So once again we're gonna have a channel three and H two S. 04 here in your nitrate in reaction. This is gonna be your aromatic ring your socks. And now you're gonna have a nitro group in the para position which is favorable due to lust eric hindrance, right? Compared to the Ortho position. So now, in our final step we can go ahead and reduce our nitro group down to an amine by reacting our nitro group with iron in the presence of HcL. So now we're going to have or aniline derivative with our primary amine that I indicated in red. So I'm gonna do the same thing here at the end. So with that being said, these are going to be all of your steps, right? So I'm gonna start from the top and um your answer in this case is going to be choice D and I'm gonna do a quick scroll through just so that you guys can see everything that we did. But um if you stuck around to the end, thank you so much for watching. And I hope you found this helpful

Synthesize from benzene. (Hint: All of these require diazonium ions.)
(d) 4-methoxyaniline

Key Concepts

Benzene and its Derivatives

Diazonium Ions

Electrophilic Aromatic Substitution

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