Predict the major product(s) that would result when molecules (a)–(i) are allowed to react under the following conditions. (iv) chlorocyclopentane, AlCl 3 , (v) 1-chloro-1-methylcyclohexane , AlCl 3 , (vi) PhCOCl, AlCl 3 . If no reaction will occur, indicate by writing NR. (a)

All right. Hi, everyone. So this question is asking us what are the major products of the reaction of benzene with 14 methyl benzyl chloride and ac three, 24 chloral, 12 dimethyl cyclops, ac three N 31 chloro 144 tri methyl cyclohexane ACL three. If no reaction occurs, write Nr and for your reference, I've gone ahead and actually drawn all three reactions on the screen here. And what we'll notice about all three reactions is that all three of them are examples of Freedom Crafts isolation or Oculus, right? In which either an AO or an O group is attached to a benzene ring or an aromatic ring with ACL three, which is a low acid as a catalyst. So in this case, starting off with our freedom craft's isolation in reaction one, the R group of our AO chloride is going to be attached to the benzene ring. So when I go ahead and I take the R group of my Azo chloride, right? This R group is going to attach itself to the benzene ring from the carbon carbon. So when you unite these two R groups together, your final product becomes phenyl peril methanol. But now lets go ahead and talk about our Oculus reactions for just a moment. I also did not mention this earlier, but for both types of reactions, actually, a hydrogen on the benzene ring gets replaced with either the A or the AO group of either your Ao chloride or Ayal or alkali. Just wanted to mention that. But when it comes to Freedom Craft's Oculus specifically, right, recall that one of the limitations of Freedom Craft's Oculus is the fact that a carpal cion forms after our Halide reacts with her le acid catalyst. Because when you form a Carbocaine during a mechanism, you always have to check for rearrangement, which means that you may not get your desired product due to rearrangement of the carbo cion. And so one way you can check for that is by just examining the carbon in your alky hide here that actually has your halogen because that is going to be your Karan after interacting with your Lewis acid. So as we can see in the structure of four chloral, 12 dimethyl cyclops after chlorine departs, right, we're going to end up with a secondary carbo car. However, our adjacent carbons also happened to be secondary, which means that rearrangement won't actually occur in this case because the carbo cion would not become more stable if it did so. And similarly, right, if I consider the structure of one chloral 144 tri methyl cyclohexane because chlorine is attached to a tertiary carbon, it would become a tertiary, cruel cion and therefore, would not need to rearrange. So the main point that I want to make here is that you should always check for whether or not your cruel cion can rearrange when you're dealing with fried grafts cul. But in this case, it so happens that that is not the case, right. So here one hydrogen from your benzene ring is going to be replaced by the ocho group of the O hide. So when I consider the product of reaction to right, I'm going to take my benzene ring and attached to my benzene ring will be my cyclops ring after I draw that a little bit better. Actually, there we go with my two methyl groups on the opposite side. And then for reaction three, here, I'm going to draw my benzene ring once again after I fix this pie bound and then attached to my bende ring will be my cyclo hexane ring with my three metal groups. And there you have it. Here are your three products of the following reactions. So just as a quick recap, right? All three of these reactions were examples of either fried craft's isolation or Fri Graft's Oculus. Now, f Freedom Crafts isolation or Oculus involves the replacement of a hydrogen on an aromatic ring with either an AZO group or an O group using either an Acyl Halide or an O Halide in the presence of a Luis acid catalyst. So in order to draw the product, right, the main point here is to combine the art groups of both starting materials together. However, extra consideration is required for fo craft's cul because carbo cion rearrangement is a concern. So with that being said, thank you so very much for watching and I hope you found this helpful.

Table of contents

Skip topic navigation

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

19. Reactions of Aromatics: EAS and Beyond

Electron Withdrawing Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Electron Withdrawing Groups

Previous problemNext problem

Problem 72a

Textbook Question

Predict the major product(s) that would result when molecules (a)–(i) are allowed to react under the following conditions. (iv) chlorocyclopentane, AlCl₃, (v) 1-chloro-1-methylcyclohexane , AlCl₃, (vi) PhCOCl, AlCl₃. If no reaction will occur, indicate by writing NR.
(a)

Verified step by step guidance

Identify the type of reaction: The presence of AlCl3 suggests a Friedel-Crafts reaction, which is a type of electrophilic aromatic substitution.

Analyze the reactants: The image shows a benzene ring, which is a common substrate for Friedel-Crafts reactions.

Consider the electrophile: In the case of chlorocyclopentane with AlCl3, the electrophile is a cyclopentyl cation formed by the interaction of chlorocyclopentane with AlCl3.

Predict the reaction: The cyclopentyl cation will attack the benzene ring, leading to the formation of a cyclopentylbenzene product.

Evaluate the conditions: Ensure that the reaction conditions are suitable for the Friedel-Crafts alkylation to occur, such as the presence of a strong Lewis acid (AlCl3) and an aromatic substrate (benzene).

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Friedel-Crafts Alkylation

Friedel-Crafts alkylation is a reaction that introduces an alkyl group into an aromatic ring using an alkyl halide and a Lewis acid catalyst like AlCl3. The catalyst helps generate a carbocation from the alkyl halide, which then attacks the electron-rich aromatic ring, forming a new carbon-carbon bond. This reaction is useful for synthesizing alkylbenzenes but can lead to polyalkylation and carbocation rearrangements.

Friedel-Crafts Acylation

Friedel-Crafts acylation involves the introduction of an acyl group into an aromatic ring using an acyl chloride and a Lewis acid catalyst such as AlCl3. This reaction forms a ketone and is generally more controlled than alkylation, as it avoids carbocation rearrangements and polyacylation. The acylium ion, generated in situ, is the electrophile that attacks the aromatic ring, leading to the formation of an aryl ketone.

Aromaticity and Electrophilic Aromatic Substitution

Aromatic compounds, like benzene, are characterized by their stability due to delocalized π-electrons. Electrophilic aromatic substitution (EAS) is a common reaction mechanism where an electrophile replaces a hydrogen atom on the aromatic ring. The stability of the aromatic system is temporarily disrupted during the formation of a sigma complex, but restored upon re-aromatization. Understanding EAS is crucial for predicting the outcome of reactions involving aromatic compounds.

Watch next

Master Activity and Directing Effects with a bite sized video explanation from Johnny

Start learning