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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5:18 minutes

Problem 33a,b

Textbook Question

What are the products of the following reactions?
a.
b.

Verified step by step guidance

Step 1: Analyze the starting material, which is an alkyl bromide (CH3CH2CH2Br). This compound contains a bromine atom attached to a propyl chain.

Step 2: The first reagent, lithium (Li), reacts with the alkyl bromide to form an organolithium compound (CH3CH2CH2Li). This is a nucleophilic species formed by replacing the bromine atom with lithium.

Step 3: The second reagent, copper(I) iodide (CuI), reacts with the organolithium compound to form a Gilman reagent (CH3CH2CH2)2CuLi. Gilman reagents are useful for coupling reactions.

Step 4: The third step involves the reaction of the Gilman reagent with the alkyl bromide provided in the reaction scheme (CH2=CHCH2Br or CH2=CHCHBrCH3). This is a coupling reaction where the Gilman reagent replaces the bromine atom in the alkyl bromide with the alkyl group from the Gilman reagent.

Step 5: The final product is formed by combining the alkyl group from the Gilman reagent with the alkyl bromide, resulting in a new carbon-carbon bond. The specific product depends on the structure of the alkyl bromide used in the third step.

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Key Concepts

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

Organolithium Reagents

Organolithium reagents, such as those formed from lithium and organic halides, are highly reactive compounds used in organic synthesis. They act as strong nucleophiles, facilitating the formation of carbon-carbon bonds by attacking electrophiles. In the given reaction, lithium likely helps to generate a lithium alkyl intermediate that can further react with copper(I) iodide.

Cuprate Reagents

Cuprate reagents, formed from the reaction of organolithium compounds with copper(I) halides, are important in organic synthesis for their ability to participate in nucleophilic substitutions. They can react with alkyl halides to form new carbon-carbon bonds, allowing for the construction of more complex molecules. The use of CuI in the reaction indicates a pathway to generate a new alkyl group.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like bromine) by a nucleophile. In this context, the organolithium and cuprate reagents act as nucleophiles that attack the carbon atom bonded to the bromine, leading to the formation of new carbon-carbon bonds. Understanding the mechanism of these reactions is crucial for predicting the products of the given transformations.

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Related Practice

Textbook Question

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(c)

Textbook Question

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(c)

Textbook Question

To this point, we have seen four reactions that can be done by Gilman reagents. What are they? What do they have in common?

Textbook Question

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(b)

Textbook Question

What are the products of the following reactions?

Textbook Question

What are the products of the following reactions? Show all stereoisomers that are formed.

Textbook Question

What product is formed when 3-methyl-2-cyclohexenone reacts with each of the following reagents?

a. CH₃MgBr followed by H₃O⁺

b. (CH₃CH₂)₂CuLi followed by H₃O⁺

Textbook Question

The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an α-bromo ester with zinc.

Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

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What are the products of the following reactions?a. b.

Key Concepts

Organolithium Reagents

Cuprate Reagents

Nucleophilic Substitution Reactions

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What are the products of the following reactions?
a.
b.