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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6:35 minutes

Problem 30a,b,c

Textbook Question

Predict the products (if any) of the following acid–base reactions.
(a) acetic acid + ammonia
(b) phthalic acid + excess NaOH
(c) p-toluic acid + potassium trifluoroacetate

Verified step by step guidance

Step 1: Understand the nature of acid-base reactions. Acid-base reactions involve the transfer of a proton (H⁺) from the acid to the base. Acids are proton donors, and bases are proton acceptors. Identify the acid and base in each reaction.

Step 2: For (a) acetic acid + ammonia: Acetic acid (CH₃COOH) is a weak acid, and ammonia (NH₃) is a weak base. The reaction involves the transfer of a proton from acetic acid to ammonia, forming ammonium ion (NH₄⁺) and acetate ion (CH₃COO⁻). Write the balanced chemical equation:

{CH 3}_{COOH} + {NH}_{3} \to {CH}_{3} {COO}_{-} + {NH}_{4} +

Step 3: For (b) phthalic acid + excess NaOH: Phthalic acid is a diprotic acid (C₆H₄(COOH)₂). In the presence of excess NaOH, both acidic protons are neutralized, forming the disodium salt of phthalic acid (C₆H₄(COONa)₂) and water. Write the balanced chemical equation:

{C 6}_{H_{4} ({COOH}_{) 2}} + 2 {NaOH}_{\to} {C 6}_{H_{4} ({COONa}_{) 2} + 2 H_{2} O}

Step 4: For (c) p-toluic acid + potassium trifluoroacetate: p-Toluic acid (C₆H₄(CH₃)(COOH)) is a weak acid, and potassium trifluoroacetate (CF₃COOK) is a weak base. The reaction involves the transfer of a proton from p-toluic acid to trifluoroacetate ion (CF₃COO⁻), forming trifluoroacetic acid (CF₃COOH) and the potassium salt of p-toluic acid (C₆H₄(CH₃)(COOK)). Write the balanced chemical equation:

{C 6}_{H_{4} ({CH}_{3}) {COOH}_{)}} + {CF 3}_{{COOK}_{\to} {CF 3}_{{COOH}_{+} {C 6}_{H_{4} ({CH}_{3}) {COOK}_{)}}}}

Step 5: Verify the products for each reaction. Ensure that the acid donates a proton to the base, and the resulting conjugate acid and conjugate base are correctly identified. Confirm that the stoichiometry of each reaction is balanced.

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Key Concepts

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

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) from an acid to a base. In these reactions, acids are proton donors, while bases are proton acceptors. Understanding the strength of the acids and bases involved is crucial, as it influences the direction of the reaction and the stability of the products formed.

Dissociation of Acids and Bases

Acids and bases dissociate in solution to form ions. For example, acetic acid (CH3COOH) dissociates into acetate ions (CH3COO-) and protons (H+). The extent of dissociation depends on the acid's strength; strong acids dissociate completely, while weak acids only partially dissociate. This concept is essential for predicting the products of the reactions.

Neutralization Reactions

Neutralization reactions occur when an acid reacts with a base to form water and a salt. In the context of the given question, identifying the products involves recognizing how the acid and base interact, leading to the formation of new compounds. For example, when phthalic acid reacts with NaOH, the result is the formation of a salt and water, illustrating the neutralization process.

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Related Practice

Textbook Question

Which of the following are considered carboxylic acid derivatives?

(a)

Textbook Question

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(d)

Textbook Question

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(e)

Textbook Question

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(ii) show what compounds would result from complete hydrolysis.

(iii) are any of the rings aromatic? Explain.

(f)

Textbook Question

Arrange each group of compounds in order of increasing acidity.

(a) phenol, ethanol, acetic acid

(b) p-toluenesulfonic acid, acetic acid, chloroacetic acid

(d) butyric acid, α-bromobutyric acid, β-bromobutyric acid

(e)

Textbook Question

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) Determine the kind of polymer (polyamide, polyester, etc.).

(ii) Draw the structures of the monomers that would be released by complete hydrolysis.

(iii) Suggest what monomers or stable derivatives of the monomers might be used to make these polymers.

(a)

Textbook Question

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) Determine the kind of polymer (polyamide, polyester, etc.).

(ii) Draw the structures of the monomers that would be released by complete hydrolysis.

(iii) Suggest what monomers or stable derivatives of the monomers might be used to make these polymers.

(b)

Textbook Question

Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.

(e) heptanoic acid

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Predict the products (if any) of the following acid–base reactions.(a) acetic acid + ammonia(b) phthalic acid + excess NaOH(c) p-toluic acid + potassium trifluoroacetate

Key Concepts

Acid-Base Reactions

Dissociation of Acids and Bases

Neutralization Reactions

Watch next

Predict the products (if any) of the following acid–base reactions.
(a) acetic acid + ammonia
(b) phthalic acid + excess NaOH
(c) p-toluic acid + potassium trifluoroacetate