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

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

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7:51 minutes

Problem 67c

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:
c.

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Identify the target compound that needs to be synthesized using the Reformatsky reaction. This will typically involve recognizing the carbonyl compound (aldehyde or ketone) and the ester that will form the organozinc reagent.

Determine the structure of the alpha-bromo ester needed to form the organozinc reagent. The alpha-bromo ester should have the same carbon skeleton as the desired product, minus the carbonyl group.

React the alpha-bromo ester with zinc metal to form the organozinc reagent. This step involves the insertion of zinc into the carbon-bromine bond, creating a nucleophilic organozinc species.

Perform the nucleophilic addition of the organozinc reagent to the carbonyl compound (aldehyde or ketone). This step involves the organozinc reagent attacking the electrophilic carbon of the carbonyl group, forming a new carbon-carbon bond.

Finally, perform a workup step, typically involving the addition of an acid, to protonate the alkoxide intermediate and yield the desired beta-hydroxy ester product.

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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 generally less reactive than Grignard reagents, making them useful in reactions where controlled reactivity is desired. These reagents are typically prepared by reacting zinc with alkyl or aryl halides, such as a-bromo esters, which are crucial for the Reformatsky reaction.

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 reduced reactivity of organozinc reagents prevents unwanted nucleophilic addition to ester groups, allowing for more selective reactions with aldehydes and ketones.

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(a)

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Textbook Question

Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed hydrolysis of an ester, indicating a. similarities. b. differences.

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