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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2:19 minutes

Problem 67a

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:
a.

Verified step by step guidance

Step 1: Understand the Reformatsky reaction mechanism. The Reformatsky reaction involves the formation of an organozinc reagent from an α-bromo ester and zinc, which then reacts with a carbonyl compound (aldehyde or ketone) to form a β-hydroxy ester.

Step 2: Identify the target compound structure. Analyze the given compound structure to determine the necessary β-hydroxy ester product that needs to be synthesized using the Reformatsky reaction.

Step 3: Select the appropriate α-bromo ester. Based on the target compound, choose an α-bromo ester that will form the desired carbon skeleton after the Reformatsky reaction. Consider the carbon chain length and functional groups present in the target compound.

Step 4: Choose the carbonyl compound. Determine the aldehyde or ketone that will react with the organozinc reagent to form the β-hydroxy ester. Ensure that the carbonyl compound complements the α-bromo ester to achieve the desired product.

Step 5: Perform the Reformatsky reaction. Mix the α-bromo ester with zinc to form the organozinc reagent, then add the chosen carbonyl compound to the reaction mixture. Allow the reaction to proceed, forming the β-hydroxy ester, which can be further purified if necessary.

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Key Concepts

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

Reformatsky Reaction

The Reformatsky reaction is a chemical reaction that involves the addition of an organozinc reagent to a carbonyl compound, typically an aldehyde or ketone. This reaction is notable for using organozinc reagents, which are less reactive than Grignard reagents, allowing for selective reactions without unwanted side reactions, such as nucleophilic addition to esters.

Organozinc Reagents

Organozinc reagents are organometallic compounds that contain a carbon-zinc bond. They are prepared by reacting zinc with organic halides, such as a-bromo esters. These reagents are valuable in organic synthesis due to their ability to act as nucleophiles in various reactions, including the Reformatsky reaction, where they selectively add to carbonyl groups.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in a carbonyl group. In the context of the Reformatsky reaction, the organozinc reagent acts as the nucleophile, adding to the carbonyl carbon of aldehydes or ketones, leading to the formation of alcohols or other products, depending on the reaction conditions.

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