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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7:05 minutes

Problem 52b

Textbook Question

Show how the following compounds can be synthesized from benzene:
b. m-chloroethylbenzene

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.

Step 2: Perform a Friedel-Crafts alkylation reaction to introduce the ethyl group onto the benzene ring. Use ethyl chloride (C₂H₅Cl) and a Lewis acid catalyst such as AlCl₃. This reaction will yield ethylbenzene.

Step 3: Carry out a chlorination reaction to introduce a chlorine atom onto the benzene ring. Use Cl₂ and a catalyst such as FeCl₃. This reaction will produce a mixture of ortho-, meta-, and para-chloroethylbenzene.

Step 4: Separate the meta-chloroethylbenzene from the mixture using techniques such as fractional distillation or chromatography, as the meta-isomer is the desired product.

Step 5: Confirm the structure of the synthesized m-chloroethylbenzene using spectroscopic methods such as NMR or IR to ensure the correct substitution pattern 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. This process is crucial for synthesizing various aromatic compounds, including m-chloroethylbenzene from benzene. The reaction typically involves the generation of a positively charged intermediate, which then loses a proton to restore aromaticity.

Regioselectivity in Substitution Reactions

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the case of m-chloroethylbenzene synthesis, understanding the directing effects of substituents on the benzene ring is essential. The presence of an ethyl group directs the incoming electrophile to the meta position relative to itself, leading to the desired product.

Chlorination of Aromatic Compounds

Chlorination is a specific type of electrophilic aromatic substitution where chlorine is introduced into an aromatic compound. This reaction often requires a catalyst, such as iron(III) chloride, to generate the electrophilic chlorine species. In the synthesis of m-chloroethylbenzene, chlorination occurs after the ethyl group has been introduced, allowing for the selective formation of the meta product.

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