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

35. Transition Metals

Negishi Coupling Reaction

Organic Chemistry

35. Transition Metals

Negishi Coupling Reaction

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4:01 minutes

Problem 24b

Textbook Question

Work backward to an appropriate organozinc halide and organohalide to make the bonds indicated by the blue arrows. There may be two possibilities for each.
(b)

Verified step by step guidance

Identify the bond indicated by the blue arrow. This bond is between the cyclopentyl group and the oxygen atom in the ether linkage.

To work backward, consider breaking the molecule at the indicated bond to form two fragments: a cyclopentyl group and an ether group.

The cyclopentyl group can be derived from a cyclopentyl organozinc halide. Consider the structure of cyclopentyl zinc bromide (C5H9ZnBr) as a potential organozinc halide.

The ether group can be derived from an organohalide. Consider the structure of 2-bromoethoxybenzene (C8H9BrO) as a potential organohalide.

Propose a reaction where the cyclopentyl zinc bromide reacts with 2-bromoethoxybenzene to form the desired ether linkage, using a coupling reaction such as the Negishi coupling.

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Key Concepts

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

Organozinc Reagents

Organozinc reagents, typically represented as RZnX, are organometallic compounds where a zinc atom is bonded to an organic group (R) and a halide (X). They are highly reactive and serve as nucleophiles in organic synthesis, allowing for the formation of carbon-carbon bonds through reactions with electrophiles. Understanding their reactivity and how they can be synthesized from organohalides is crucial for constructing complex organic molecules.

Organohalides

Organohalides, or haloalkanes, are organic compounds containing at least one halogen atom (F, Cl, Br, I) bonded to a carbon atom. They are important intermediates in organic synthesis, as they can undergo various reactions, including nucleophilic substitution and elimination. Recognizing the structure and reactivity of organohalides is essential for determining how to create the desired organozinc halide for bond formation.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (often a halide) in a molecule with a nucleophile. These reactions can occur via two main mechanisms: SN1 (unimolecular) and SN2 (bimolecular), each with distinct kinetics and stereochemical outcomes. Understanding these mechanisms is vital for predicting the products of reactions involving organozinc and organohalide compounds, especially when constructing new carbon-carbon bonds.

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