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

EAS:Retrosynthesis

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

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6:30 minutes

Problem 19a

Textbook Question

Show how you would synthesize the following aromatic derivatives from benzene.
a. p-tert-butylnitrobenzene

Verified step by step guidance

Step 1: Begin with benzene as the starting material. Benzene is an aromatic compound with a planar ring structure and alternating double bonds.

Step 2: Introduce the tert-butyl group onto the benzene ring through Friedel-Crafts alkylation. Use tert-butyl chloride (C(CH₃)₃Cl) as the alkylating agent and aluminum chloride (AlCl₃) as the catalyst. This reaction will yield tert-butylbenzene.

Step 3: Nitrate the tert-butylbenzene to introduce the nitro group (-NO₂). Perform an electrophilic aromatic substitution reaction using a nitrating mixture of concentrated sulfuric acid (H₂SO₄) and concentrated nitric acid (HNO₃). This reaction will add the nitro group to the para position relative to the tert-butyl group due to steric hindrance and electronic effects.

Step 4: Carefully control the reaction conditions to ensure selective nitration at the para position. The tert-butyl group is an electron-donating group, which directs the incoming nitro group to the para position.

Step 5: Purify the product, p-tert-butylnitrobenzene, using techniques such as recrystallization or chromatography to isolate the desired compound from any side products or unreacted starting materials.

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Key Concepts

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

Electrophilic Aromatic Substitution (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for synthesizing various aromatic compounds, as it allows for the introduction of different functional groups onto the benzene ring. Understanding the mechanism of EAS, including the role of catalysts and the stability of intermediates, is essential for predicting the outcomes of reactions involving aromatic compounds.

Activating and Deactivating Groups

In the context of EAS, substituents on the aromatic ring can either activate or deactivate the ring towards further substitution. Activating groups, such as alkyl groups, increase the electron density of the ring, making it more reactive towards electrophiles. Conversely, deactivating groups, like nitro groups, withdraw electron density and make the ring less reactive. Recognizing how these groups influence the position and rate of substitution is vital for successful synthesis.

Ortho/Para vs. Meta Directing Effects

The directing effects of substituents on an aromatic ring determine where new substituents will be added during EAS. Ortho and para directing groups favor substitution at the 2 and 4 positions relative to themselves, while meta directing groups favor substitution at the 3 position. Understanding these patterns is essential for predicting the structure of the final product, such as p-tert-butylnitrobenzene, and for planning the synthetic route effectively.

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Show how you would synthesize the following aromatic derivatives from benzene.a. p-tert-butylnitrobenzene

Key Concepts

Electrophilic Aromatic Substitution (EAS)

Activating and Deactivating Groups

Ortho/Para vs. Meta Directing Effects

Watch next

Show how you would synthesize the following aromatic derivatives from benzene.
a. p-tert-butylnitrobenzene