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

Previous problemNext problem

7:36 minutes

Problem 90

Textbook Question

Identify compounds A and B:

Verified step by step guidance

Step 1: Analyze the first reaction. The compound X reacts with a Gilman reagent (R2CuLi), which is known for performing conjugate addition to α,β-unsaturated carbonyl compounds. This suggests that X is likely an α,β-unsaturated ketone or aldehyde.

Step 2: The Gilman reagent adds one of its alkyl groups to the β-carbon of the α,β-unsaturated system in X. This results in compound Y, which is a substituted ketone or aldehyde. The reaction is followed by acidic workup (H3O+), ensuring the stability of the product.

Step 3: Analyze the second reaction. Compound Y reacts with an organometallic reagent, specifically a Grignard reagent (R-MgBr). Grignard reagents typically add to the carbonyl group of ketones or aldehydes, forming an alcohol after acidic workup.

Step 4: The Grignard reagent adds its alkyl group to the carbonyl carbon of Y, forming a tertiary alcohol after the acidic workup. The final product is a tertiary alcohol with a cyclohexane ring and multiple substituents.

Step 5: Based on the structure of the final product provided in the image, deduce the structures of compounds X and Y by working backward. Compound X is likely an α,β-unsaturated ketone, and compound Y is the intermediate ketone formed after the conjugate addition of the Gilman reagent.

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.

Grignard Reagents

Grignard reagents are organomagnesium compounds, typically represented as R-MgX, where R is an organic group and X is a halogen. They are highly reactive and serve as nucleophiles in organic synthesis, allowing for the formation of carbon-carbon bonds. In the reaction shown, a Grignard reagent (MgBr) is used to add to a carbonyl compound, facilitating the formation of alcohols.

Organocuprates

Organocuprates, or Gilman reagents, are organometallic compounds containing copper, typically represented as R2CuLi. They are less reactive than Grignard reagents and are used for selective carbon-carbon bond formation. In the reaction depicted, an organocuprate is employed to react with compound X, leading to the formation of compound Y through a nucleophilic addition.

Acid Workup

An acid workup is a common step in organic synthesis that involves the addition of an acid, such as H3O+, to neutralize basic reaction conditions and protonate intermediates. This step is crucial for converting reactive intermediates into stable products, such as alcohols. In the provided reaction scheme, the acid workup is essential for converting the Grignard and organocuprate reactions into the final alcohol products.

Watch next

Master Intro to Predict the Product with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

What bromo-substituted compound would be required to react with (CH₂=CH)₂CuLi in order to form each of the following compounds?

Textbook Question

What alkyl halide reacts with lithium divinylcuprate [(CH₂=CH)₂CuLi] for the synthesis of each of the following compounds?

Textbook Question

What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?

Textbook Question

What are the products of the following reactions?

Textbook Question

A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene (C₆H₅-CH₃) when it reacts with magnesium shavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.

Textbook Question

What is the major product of each of the following reactions?

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

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:

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap