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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Problem 74c

Textbook Question

Suggest a synthesis of each of the molecules shown beginning with benzene.
(c)

Verified step by step guidance

Start with benzene as the base molecule. The target molecule is 2,4-dichloroacetophenone, which requires the introduction of two chlorine atoms and an acetyl group onto the benzene ring.

Perform a Friedel-Crafts acylation to introduce the acetyl group. Use acetyl chloride (CH3COCl) and aluminum chloride (AlCl3) as the catalyst to add the acetyl group to the benzene ring, forming acetophenone.

Next, perform a chlorination reaction to introduce the chlorine atoms. Use chlorine (Cl2) in the presence of a Lewis acid catalyst like iron(III) chloride (FeCl3) to add chlorine atoms to the ortho and para positions relative to the acetyl group.

Ensure that the reaction conditions favor the formation of the 2,4-dichloroacetophenone by controlling the temperature and the amount of chlorine used to avoid over-chlorination.

Finally, purify the product using techniques such as recrystallization or column chromatography to isolate the desired 2,4-dichloroacetophenone 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, such as benzene. This reaction is crucial for synthesizing various substituted aromatic compounds. The stability of the aromatic system allows for the introduction of different functional groups, which can be further manipulated in subsequent reactions.

Reactivity of Benzene Derivatives

Benzene derivatives exhibit unique reactivity patterns due to the presence of substituents that can either activate or deactivate the ring towards electrophilic attack. For instance, electron-donating groups enhance reactivity, while electron-withdrawing groups decrease it. Understanding these effects is essential for predicting the outcomes of synthetic routes starting from benzene.

Functional Group Transformations

Functional group transformations involve converting one functional group into another through various chemical reactions. In the context of synthesizing the given molecule from benzene, transformations such as oxidation, halogenation, and substitution are key. Recognizing how to manipulate these functional groups allows chemists to design effective synthetic pathways to achieve desired products.

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Open Question

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

c. Give two ways to prepare b-phenylethylamine from b-phenylethyl chloride.

Open Question

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

d. How can b-phenylethylamine be prepared from benzyl chloride?

Textbook Question

Ibuprofen is the active ingredient in pain relievers such as Advil, Motrin, and Nuprin. How can ibuprofen be synthesized from benzene?

Textbook Question

Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.

a. Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion, CH3C≡O+. Be careful to draw all the resonance structures of the intermediate.

Textbook Question

Acetohexamide is used to treat type 2 diabetes that cannot be well controlled by diet alone. Fill in the blanks of the synthetic scheme used to synthesize acetohexamide. [Hints have been provided below each step.]

Textbook Question

Predict the product(s) of each of the following multistep reactions.

(b)

Textbook Question

Fluoxetine, an antidepressant, is better known as Prozac®. Suggest reagents that could be used to make the indicated C–O bond of fluoxetine. [Note that CF₃, an electron-withdrawing group, is para to where the new bond will be formed.]

Open Question

Provide the reaction for each of the following reaction steps

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Suggest a synthesis of each of the molecules shown beginning with benzene.(c)

Key Concepts

Electrophilic Aromatic Substitution (EAS)

Reactivity of Benzene Derivatives

Functional Group Transformations

Watch next

Suggest a synthesis of each of the molecules shown beginning with benzene.
(c)