Show how the following compounds can be synthesized from...

Key Concepts

Functional Group Interconversion

This concept involves transforming an existing functional group into another to achieve the desired molecular structure. In multistep synthesis from benzene, it is often necessary to modify side chains or substitute groups, through processes like oxidation, reduction, or other chemical reactions, to access functionalities that cannot be directly installed via electrophilic aromatic substitution.

Electrophilic Aromatic Substitution (EAS)

EAS is a fundamental reaction mechanism in aromatic chemistry where an electrophile replaces a hydrogen atom on a benzene ring. This class of reactions forms the basis for introducing various substituents onto benzene, allowing further modifications and the construction of more complex molecules.

Friedel-Crafts Alkylation and Acylation

These are specific types of electrophilic aromatic substitution reactions used to add alkyl or acyl groups to aromatic rings. Friedel-Crafts alkylation attaches an alkyl chain directly to benzene, while Friedel-Crafts acylation introduces an acyl group, which can be further manipulated. Both reactions typically involve a Lewis acid catalyst to facilitate the formation of the active electrophile.

Substituent Effects and Directing Groups

Understanding the electronic effects of substituents already present on the benzene ring is essential as they influence the reactivity and orientation during further electrophilic substitutions. Electron-donating groups tend to activate the ring and direct new substituents to the ortho and para positions, while electron-withdrawing groups deactivate the ring and direct to the meta position.

Transcript

00:04 Let's try some synthesis of aromatic compounds.

00:07 How would we make the molecule on the right from benzene? well, the best way to approach this is to identify what groups we have added onto our rain.

00:20 We've got a nitric group and a carbonyl group.

00:25 And we know that the best way for carbonyles is fredel craft.

00:31 A salation, that is.

00:35 And we know that nitrous, a nitro group is from, nitrification which is reacting or nitration like that which is reacting hn of 3 with h2s of 4 now the question is what should we do first well we know that this is meta directing and we know that this is also meta directing so at first it looks like we could do either way however however, if we look at the fidelc - if we look at the addition of the ketone, we know that it's fidelcraft's aisolation, which means that it cannot be done on a benzene that is already metadirecting, or it cannot be done at an aromatic compound that is already metadirecting.

01:36 It can only be done at orthoparidirecting, which means we need to add that first, otherwise the reaction wouldn't occur.

01:46 So first, we'll add our acyl chloride in the presence of our catalyst, follow it up with water, and we'll have our ketone.

02:10 And then we will use our nitration reaction, and that is how we'd synthesize that compound.

02:24 Let's try this one.

02:27 Well, we have a carbonyl group, and we have a sulfonic acid group.

02:35 The carbonyl group is metadirecting, and the sulfonic acid group is, well, also metadirecting...

Please give Ace some feedback