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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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6:29 minutes

Problem 26

Textbook Question

What organocuprate reagent would you use for the following substitutions?
(a)
(b)

Verified step by step guidance

Step 1: Analyze the transformations in both reactions. In (i), the iodine atom on the benzene ring is replaced by an alkyl group. In (ii), the bromine atom on the α-carbon of a ketone is replaced by an alkyl group.

Step 2: Recognize that organocuprate reagents (R2CuLi) are commonly used for substitution reactions where halides are replaced by alkyl groups. These reagents are nucleophilic and can perform SN2-type substitutions.

Step 3: For reaction (i), identify the alkyl group being introduced (isopropyl group). The organocuprate reagent required would be (CH3)2CHCuLi, where the isopropyl group is the nucleophile.

Step 4: For reaction (ii), identify the alkyl group being introduced (ethyl group). The organocuprate reagent required would be CH3CH2CuLi, where the ethyl group is the nucleophile.

Step 5: Ensure the reaction conditions are suitable for organocuprate substitution, typically involving a polar aprotic solvent like THF and low temperatures to prevent side reactions.

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Key Concepts

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

Organocuprate Reagents

Organocuprates, or Gilman reagents, are organometallic compounds containing copper that are used in nucleophilic substitution reactions. They are typically formed by reacting an organolithium compound with copper(I) halides. These reagents are particularly useful for performing substitutions on alkyl halides, allowing for the formation of carbon-carbon bonds in organic synthesis.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. The two main mechanisms are SN1, which involves a two-step process with a carbocation intermediate, and SN2, which is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. Understanding these mechanisms is crucial for predicting the outcomes of reactions involving organocuprates.

Stereochemistry in Substitution Reactions

Stereochemistry refers to the spatial arrangement of atoms in molecules and is critical in substitution reactions. In SN2 reactions, the nucleophile attacks from the opposite side of the leaving group, leading to inversion of configuration at the chiral center. In contrast, SN1 reactions can lead to racemic mixtures due to the planar nature of the carbocation intermediate. Recognizing the stereochemical implications is essential for predicting the products of reactions involving organocuprates.

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Related Practice

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(b) 1-chloro-1-ethylcyclopentane

Textbook Question

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(a)

Textbook Question

Show how this 1° alcohol can be made from the following:

(b) formaldehyde

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(a)

Textbook Question

What products would you expect from the following reactions?

(a)

(b)

Textbook Question

Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.

a. 3-phenylprop-1-ene

Textbook Question

Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.

b. 5-methylhex-2-ene

Textbook Question

Show how you would add a Grignard reagent to an ester or a nitrile to synthesize

(a) 4-phenylheptan-4-ol.

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What organocuprate reagent would you use for the following substitutions?(a) (b)

Key Concepts

Organocuprate Reagents

Nucleophilic Substitution Mechanisms

Stereochemistry in Substitution Reactions

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What organocuprate reagent would you use for the following substitutions?
(a)
(b)