Table of contents

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

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3:59 minutes

Problem 50i

Textbook Question

Predict the major products formed when benzene reacts (just once) with the following reagents.
(i) iodine + HNO₃

Verified step by step guidance

Step 1: Recognize the type of reaction. This is an electrophilic aromatic substitution (EAS) reaction, where benzene reacts with iodine (I₂) in the presence of nitric acid (HNO₃) to form a substituted benzene derivative.

Step 2: Understand the role of HNO₃. Nitric acid acts as an oxidizing agent in this reaction, converting iodine (I₂) into the electrophilic species I⁺ (iodonium ion), which is necessary for the substitution reaction.

Step 3: Identify the electrophile. The electrophile in this reaction is the iodonium ion (I⁺), which will attack the benzene ring.

Step 4: Describe the mechanism. The benzene ring donates a pair of π-electrons to the electrophile (I⁺), forming a sigma complex (also called an arenium ion). This intermediate is stabilized by resonance.

Step 5: Regenerate aromaticity. A proton (H⁺) is removed from the sigma complex by a base (often H₂O or NO₃⁻), restoring the aromaticity of the benzene ring and yielding the final product, iodobenzene (C₆H₅I).

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this process, the aromatic system retains its stability and aromaticity, which is crucial for understanding how benzene reacts with various reagents. The reaction typically involves the formation of a sigma complex, followed by deprotonation to restore the aromatic character.

Iodination of Aromatic Compounds

Iodination of aromatic compounds involves the introduction of iodine into the aromatic ring, often facilitated by a Lewis acid catalyst. In the presence of nitric acid (HNO3), iodine can generate an electrophilic species that can react with benzene. This reaction is significant as it demonstrates how halogens can be introduced into aromatic systems, impacting their reactivity and properties.

Nitration and its Role in Electrophilic Reactions

Nitration is the process of introducing a nitro group (-NO2) into an aromatic compound, typically using a mixture of concentrated nitric acid and sulfuric acid. In the context of the given reaction, HNO3 can act as a source of the nitronium ion (NO2+), which is a potent electrophile. Understanding nitration is essential for predicting the products of reactions involving benzene and other electrophiles, as it influences the regioselectivity of subsequent substitutions.

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Related Practice

Textbook Question

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(e)

Textbook Question

The first step of a reaction called electrophilic aromatic substitution is as follows:

If this step is rate-determining for the overall reaction, which benzene derivative would you expect to react most quickly? Which would react most slowly?

(a)

Textbook Question

The nitro group directs electrophilic aromatic substitution to the meta position. After reduction by hydrogenation, to which carbon(s) does it direct?

Textbook Question

Predict the major product of the following electrophilic aromatic substitution reactions.

(b)

Textbook Question

Predict the major products formed when benzene reacts (just once) with the following reagents.

d. bromine + a nail

Textbook Question

Draw the product(s) of each of the following reactions:

a. benzoic acid + HNO₃/H₂SO₄

b. isopropylbenzene + Cl₂ + FeCl₃

Textbook Question

What is the major product(s) of each of the following reactions?