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

Saponification

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Saponification

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1:43 minutes

Problem 47a

Textbook Question

Predict the products of saponification of the following esters.
(a)

Verified step by step guidance

Step 1: Understand the concept of saponification. Saponification is the base-catalyzed hydrolysis of an ester, resulting in the formation of a carboxylate salt and an alcohol. The reaction typically involves a strong base like NaOH or KOH.

Step 2: Analyze the given ester structure. The ester provided is phenyl formate (HCOOPh), where the ester functional group consists of a formyl group (HCO-) and a phenyl group (Ph).

Step 3: Write the general reaction for saponification. The ester reacts with a strong base (e.g., NaOH) to produce a carboxylate salt and an alcohol. In this case, the formyl group will form a formate ion (HCOO⁻), and the phenyl group will form phenol (C₆H₅OH).

Step 4: Break down the reaction mechanism. The hydroxide ion (OH⁻) attacks the carbonyl carbon of the ester, leading to the cleavage of the ester bond. This results in the formation of the carboxylate ion and the alcohol.

Step 5: Summarize the products. The saponification of phenyl formate will yield sodium formate (HCOONa, if NaOH is used) and phenol (C₆H₅OH) as the final products.

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Key Concepts

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

Saponification

Saponification is a chemical reaction that involves the hydrolysis of esters in the presence of a strong base, typically sodium hydroxide (NaOH) or potassium hydroxide (KOH). This process breaks the ester bond, resulting in the formation of an alcohol and a carboxylic acid salt, commonly known as soap. Understanding this reaction is crucial for predicting the products when esters undergo saponification.

Esters

Esters are organic compounds formed from the reaction of an alcohol and a carboxylic acid, characterized by the functional group -COO-. They are often responsible for the pleasant aromas of fruits and flowers. In the context of saponification, recognizing the structure of the ester, including the alkyl and aryl groups, is essential for determining the resulting products after the reaction.

Hydrolysis

Hydrolysis is a chemical process in which water is used to break down a compound. In the case of saponification, hydrolysis refers to the reaction of the ester with water, facilitated by a base, leading to the formation of an alcohol and a carboxylic acid. Understanding hydrolysis is key to predicting the products of saponification, as it directly relates to how the ester is converted into its constituent parts.

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Related Practice

Textbook Question

Suppose we have some optically pure (R)-2-butyl acetate that has been 'labeled' with the heavy ¹⁸O isotope at one oxygen atom as shown.

(a) Draw a mechanism for the hydrolysis of this compound under basic conditions. Predict which of the products will contain the ¹⁸O label. Also predict whether the butan-2-ol product will be pure (R), pure (S), or racemized.