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

Previous problemNext problem

4:42 minutes

Problem 22

Textbook Question

a. Does a coupling reaction have to be used to synthesize p-dipropylbenzene?
b. Can a coupling reaction be used to synthesize p-dipropylbenzene?

Verified step by step guidance

Step 1: Understand the structure of p-dipropylbenzene. It is a benzene ring with two propyl groups (-CH2CH2CH3) attached at the para positions (1,4 positions on the benzene ring).

Step 2: Analyze part (a). A coupling reaction typically involves the formation of a new carbon-carbon bond between two organic fragments, often using a catalyst. Consider whether a coupling reaction is necessary to attach the two propyl groups to the benzene ring. Note that simpler methods, such as Friedel-Crafts alkylation, might be more direct for this synthesis.

Step 3: Analyze part (b). Determine if a coupling reaction could theoretically be used to synthesize p-dipropylbenzene. For example, you could consider using a Suzuki or Heck coupling reaction, which are common in organic synthesis, to attach the propyl groups to the benzene ring.

Step 4: Evaluate the practicality of using a coupling reaction. While it might be possible to use a coupling reaction, consider whether it is the most efficient or practical method compared to other synthetic routes, such as direct alkylation.

Step 5: Conclude by comparing the necessity and feasibility of using a coupling reaction for this synthesis. Highlight that while a coupling reaction could be used, it may not be the most straightforward or commonly employed method for synthesizing p-dipropylbenzene.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Coupling Reactions

Coupling reactions are organic reactions where two fragments are joined together, often involving the formation of a new carbon-carbon bond. Common examples include Suzuki and Heck reactions, which utilize transition metals as catalysts. Understanding these reactions is crucial for synthesizing complex organic molecules, such as p-dipropylbenzene, from simpler precursors.

Substitution Reactions

Substitution reactions involve replacing one atom or group in a molecule with another. In the context of aromatic compounds, electrophilic aromatic substitution (EAS) is a key mechanism that allows for the introduction of substituents onto the benzene ring. This concept is essential for understanding how to synthesize p-dipropylbenzene through direct substitution methods rather than coupling.

Aromatic Compounds

Aromatic compounds are cyclic, planar molecules with delocalized pi electrons, which confer unique stability and reactivity. The properties of aromaticity influence how these compounds react, particularly in substitution reactions. Recognizing the structure and reactivity of aromatic compounds is vital for determining the feasibility of synthesizing p-dipropylbenzene through various organic reactions.

Watch next

Master Activity and Directing Effects with a bite sized video explanation from Johnny

Start learning