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

Carboxylic Acid Derivatives

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid Derivatives

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3:24 minutes

Problem 48b

Textbook Question

Show how you would accomplish the following syntheses in good yields.
(b)

Verified step by step guidance

Step 1: Analyze the starting material and the target molecule. The starting material is benzoic acid (C₆H₅COOH), and the target molecule is phenyl acetate (C₆H₅COOCOCH₃). This transformation involves converting the carboxylic acid group into an ester group.

Step 2: Recognize the reaction type. This is an esterification reaction, specifically a reaction between a carboxylic acid and an acid anhydride to form an ester.

Step 3: Select the appropriate reagent. To achieve this transformation, use acetic anhydride ((CH₃CO)₂O) as the reagent. Acetic anhydride reacts with benzoic acid to form phenyl acetate and acetic acid as a byproduct.

Step 4: Outline the reaction conditions. The reaction typically requires mild heating to facilitate the esterification process. No catalyst is necessary because acetic anhydride is reactive enough to proceed without additional activation.

Step 5: Write the reaction mechanism. The carboxylic acid group of benzoic acid attacks the carbonyl carbon of acetic anhydride, leading to the formation of phenyl acetate and acetic acid. Ensure the reaction is carried out under anhydrous conditions to prevent hydrolysis of the anhydride.

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Key Concepts

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

Carboxylic Acids

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are known for their acidic properties and can undergo various reactions, including esterification and conversion to derivatives. Understanding their structure and reactivity is crucial for synthesizing derivatives, as shown in the provided reaction.

Carboxylic Acid Derivatives

Carboxylic acid derivatives include compounds such as esters, amides, and anhydrides, which retain the carboxyl group but have different substituents. These derivatives can be synthesized from carboxylic acids through various chemical reactions, often involving nucleophilic acyl substitution. Recognizing the types of derivatives and their formation mechanisms is essential for successful synthesis.

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of a carboxylic acid or its derivative, leading to the replacement of a leaving group. This mechanism is key in converting carboxylic acids into their derivatives, as it allows for the introduction of new functional groups while maintaining the carbon skeleton. Mastery of this concept is vital for achieving good yields in synthesis.

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Related Practice

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(g)

Textbook Question

Show how you would convert the following starting materials to the indicated nitriles:

(b) phenylacetic acid → 3-phenylpropionitrile

Textbook Question

Show how you would convert the following starting materials to the indicated nitriles:

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(a)

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(h)

Textbook Question

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(c)

Textbook Question

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(d)

Textbook Question

Peroxyacetic acid (bp = 105 °C) has a lower boiling point than acetic acid (bp = 118 °C), even though peroxyacetic acid has a higher molecular weight. Explain why peroxyacetic acid is more volatile than acetic acid.

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Show how you would accomplish the following syntheses in good yields.(b)

Key Concepts

Carboxylic Acids

Carboxylic Acid Derivatives

Nucleophilic Acyl Substitution

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Show how you would accomplish the following syntheses in good yields.
(b)