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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2:15 minutes

Problem 85d

Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
d.

Verified step by step guidance

Step 1: Analyze the starting material and the target compound. The starting material is styrene (C6H5-CH=CH2), and the target compound is phenylbutanoic acid (C6H5-CH2-CH2-COOH). The transformation involves adding two carbons and converting the alkene into a carboxylic acid.

Step 2: Perform a hydroboration-oxidation reaction on the styrene. Use BH3 (borane) followed by H2O2 (hydrogen peroxide) and NaOH (sodium hydroxide) to convert the alkene into a primary alcohol (C6H5-CH2-CH2-OH). This reaction adds water across the double bond in an anti-Markovnikov fashion.

Step 3: Oxidize the primary alcohol to a carboxylic acid. Use a strong oxidizing agent such as KMnO4 (potassium permanganate) or CrO3 (chromium trioxide) in acidic conditions to convert the alcohol group (-CH2OH) into a carboxylic acid (-COOH).

Step 4: Verify the structure of the product. Ensure that the phenyl group (C6H5-) remains intact and the two-carbon chain is correctly added, leading to the formation of phenylbutanoic acid.

Step 5: Review the reaction conditions and reagents used to ensure compatibility with the functional groups present in the starting material and the target compound.

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Key Concepts

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

Ester Hydrolysis

Ester hydrolysis is a chemical reaction where an ester reacts with water in the presence of an acid or base to form an alcohol and a carboxylic acid. In acid-catalyzed hydrolysis, the ester is protonated, making it more susceptible to nucleophilic attack by water, leading to the cleavage of the ester bond. This reaction is important in organic synthesis and can be used to convert esters back to their corresponding carboxylic acids and alcohols.

Reagents in Organic Synthesis

In organic synthesis, various reagents are employed to facilitate chemical reactions. Common reagents include acids, bases, oxidizing agents, and reducing agents, each serving specific roles in transforming reactants into desired products. Understanding the function and mechanism of these reagents is crucial for predicting the outcome of reactions and designing synthetic pathways.

Mechanism of Acid-Catalyzed Reactions

The mechanism of acid-catalyzed reactions involves the donation of a proton (H+) from the acid to the reactant, enhancing its electrophilicity. This step often leads to the formation of a more reactive intermediate, which can then undergo further reactions, such as nucleophilic attack. Familiarity with these mechanisms allows chemists to manipulate reaction conditions to favor the formation of specific products.

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