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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6:14 minutes

Problem 80d

Textbook Question

How can you prepare the following compounds with benzene as one of the starting materials?
d.

Verified step by step guidance

Step 1: Begin with benzene as the starting material. Benzene is an aromatic compound with alternating double bonds in a six-membered ring structure.

Step 2: Perform a hydroxylation reaction to introduce hydroxyl (-OH) groups onto the benzene ring. This can be achieved using a strong oxidizing agent such as potassium permanganate (KMnO4) or a similar reagent under acidic or neutral conditions.

Step 3: Ensure the reaction conditions favor the formation of multiple hydroxyl groups on the benzene ring. The hydroxylation process typically leads to the formation of hydroxybenzene derivatives, such as phenol, and further oxidation can yield compounds with multiple hydroxyl groups.

Step 4: Adjust the reaction conditions to achieve the specific substitution pattern seen in the target compound. This may involve controlling the stoichiometry of the oxidizing agent and reaction temperature to ensure the hydroxyl groups are added at the correct positions.

Step 5: Purify the final product using techniques such as recrystallization or chromatography to isolate the desired compound with three hydroxyl groups in the 1,2,3 positions on the benzene ring.

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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, such as benzene. This reaction is crucial for introducing various functional groups into aromatic compounds. The process typically involves the formation of a sigma complex, followed by deprotonation to restore aromaticity.

Hydroxyl Group Introduction

The introduction of hydroxyl groups (-OH) into aromatic compounds can be achieved through various EAS reactions, such as nitration followed by reduction or direct hydroxylation. The presence of hydroxyl groups can significantly influence the reactivity and properties of the aromatic compound, making it more susceptible to further substitutions due to the activating nature of the -OH group.

Ortho/Para vs. Meta Directing Effects

In EAS reactions, substituents on the aromatic ring can influence the position of new substituents. Activating groups, like hydroxyl, direct incoming electrophiles to the ortho and para positions relative to themselves, while deactivating groups direct them to the meta position. Understanding these directing effects is essential for predicting the outcome of multi-step synthesis involving benzene derivatives.

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