In particular you should be prepared to show how an aromatic compound containing two or more substituents could be synthesized, taking care to introduce the substituents into the ring in the correct order. As you can see, the product is now going to be a mono-halogenated benzene, which is great. One combination would be HF and a double bond. And you want to use the same X in both of them as you're going to see in the catalyst, it might actually matter. design multistep syntheses using the reactions discussed in this and the preceding chapters. Clutch Prep is not sponsored or endorsed by any college or university. They literally are saying feed me electrons. As of this date, Scribd will manage your SlideShare account and any content you may have on SlideShare, and Scribd's General Terms of Use and Privacy Policy will apply. Alkylation gives us an alkyl group, literally just a R group. Great job, guys! All right. That's what we have at the top. The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Enter your friends' email addresses to invite them: If you forgot your password, you can reset it. Chemistry of Benzene• Benzene is an organic chemical compound with the molecular formula C6 H6.. Benzene is a colorless and highly flammable liquid .• Benzene is a natural constituent of crude oil, and may be synthesized from other compounds present in … Sulfonic acid. The periodic table—the transition metals, Topic 11: Measurement and data processing, 3. But they're really the same thing. C) a Lewis acid. 26 - Amino Acids, Peptides, and Proteins, Resonance Theory of EAS Directing Effects. With it being half term here in the UK, what better use of sudden vast amounts of free time could […] Chemistry | Pearltrees says: February 25, 2015 at 6:38 am […] Organic Chemistry Reaction Map. Ch. When we discuss nucleophilic aromatic substitution, you will see that it can be achieved by two different mechanisms, one of which involves the formation of an unusual looking intermediate, benzyne. Benzene Concept Map. These have been made according to the syllabus 9701 and cover all the relevant topics for examination in March/June. CIE A-Level 26: Benzene and Its Compounds Notes: © 2018 A* Chemistry. Aromatic compounds are extremely important for all kinds of pharmaceuticals. Maybe making the next Viagra. Edit. Now customize the name of a clipboard to store your clips. Well, first of all, the product of sulfonation is going to make what we call a sulfonic acid group. 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Just keep in mind that the R group is what stays, whatever we had as an R group. I know that was a lot. That's going to become important later when we look into the mechanism. Well, carbocations by definition are super strong electrophiles because they have an empty p orbital. And that's going to give us actually what we call an acyl group. There's different ways to represent these reactions, but they're all really the same thing, steam, dilute H2SO4, that would take it to the desulfonation back to the original benzene. All Rights Reserved. Those are the two Friedel-Crafts reactions. You will also see how alkyl and acyl groups can be introduced on to an aromatic ring; how, once introduced, alkyl groups can be converted to carboxyl groups; and how bromine can be introduced to the alkyl side chain of alkylbenzene. Slideshare uses cookies to improve functionality and performance, and to provide you with relevant advertising. Join thousands of students and gain free access to 63 hours of Organic videos that follow the topics your textbook covers. Let's discuss what that is. We need a catalyst, guys. Memorising the reagents and conditions for these benzene reactions is an integral part of Organic Chemistry, so I've added 2 short memory tests. Now what we see is that the X actually doesn't end up on the benzene. I do want to just help you guys understand what a nitro group is by drawing it. Edit. 12 - Alcohols, Ethers, Epoxides and Thiols, Ch. So a carbonyl group. As previously discussed, benzene is going to require very strong electrophiles in order to react through EAS. Also, one thing to keep in mind is that nitric acid can also be written differently. Hope that makes sense so far. Formulae, stoichiometry and the mole concept, 7. 69% average accuracy. Regardless of how you draw it, it's really going to produce the same product. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. That Lewis acid catalyst for Friedel-Crafts reactions is going to be an aluminum catalyst, so it's going to be AlX3. It can be written as HONO2. Friedel-Crafts acylation would use an acid chloride. Now, we're not going to have to go back and remember every single carbocation intermediated reaction. Slideshare uses cookies to improve functionality and performance, and to provide you with relevant advertising. Aromatic compounds usually undergo which type of reaction? 0. 26: Benzene and Its Compounds. The whole point here is at the end that we're adding some kind of R group to our benzene ring. It's the most common version. But just keep in mind that you can also generate this electrophile just through using concentrated HNO3. Whereas acylation gives us a acyl group. However, this reaction proceeds slowly, which is inconvenient (dangerous) since hot, conc. It's important that when you discuss this mechanism, you call it EAS halogenation because specifically, this is the one that requires a Lewis acid catalyst. It's important to distinguish this mechanism from another reaction we learned in the past, which is called halogenation. As you can see they use the same reagents or the same Lewis acid catalyst, but there are some differences that we'll explore later. D) peroxide. For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. The single bonded O has a negative charge. Awesome. That would be one, these are very common. Topic: Benzene (Arenes), Organic Chemistry, A Level Chemistry, Singapore Another combination that can produce carbocations which be actually BF3, so a strong Lewis acid with alcohol. E) ultraviolet light. Again, I'm writing it in multiple ways so that you're not going to get stumped on an exam or on an online homework. 1. Usually a ketone. Download free Organic Chemistry concept maps here! Play this game to review Organic Chemistry. The next one we want to discuss is nitration. 27 times. Missed the LibreFest? Notes for the CIE O Level Chemistry – 26: Benzene and Its Compounds. Now let's work on the Friedel-Crafts reactions. You can make a million bucks. If you continue browsing the site, you agree to the use of cookies on this website. You're going to wind up getting a carbocation on the square on cyclobutane and then that winds up getting attacked by the benzene. We're going to see later how BF3 and alcohol can also produce carbocation-like structures that will react with benzene and produce an R group. 4 months ago. Clipping is a handy way to collect important slides you want to go back to later. If you can add R groups and make them bigger, that's awesome. What ends up on the benzene is the R group. A ketone. For the rest of the reactions that I work with you guys, I'm always going to be working with AlCl3. Let's use red. A) a hydroxide ion. Some professors and texts might even refer to these as Friedel-Crafts reactions, but I prefer to discuss more their mechanism and highlight the fact that they are carbocation intermediated reactions, so you can really instead of trying to remember how that's a Friedel-Crafts, think of it more just as a carbocation reaction that will basically tempt the benzene to react with it.