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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4:17 minutes

Problem 63b

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)

Verified step by step guidance

Step 1: Analyze the polymer structure provided in the image. The repeating unit contains amide bonds (-CONH-) between segments of the polymer chain, indicating that this is a polyamide. Polyamides are formed through condensation reactions between amines and carboxylic acids.

Step 2: To determine the monomers released by complete hydrolysis, focus on breaking the amide bonds. Hydrolysis of the amide bonds will yield two types of monomers: a diamine and a dicarboxylic acid. Specifically, the hydrolysis will split the polymer at the -CONH- linkages.

Step 3: Draw the structures of the monomers. The diamine monomer will be hexamethylenediamine (H₂N-(CH₂)₆-NH₂), and the dicarboxylic acid monomer will be adipic acid (HOOC-(CH₂)₄-COOH). These are the building blocks released upon hydrolysis.

Step 4: Suggest the monomers or stable derivatives used to synthesize the polymer. The polymer can be synthesized by reacting hexamethylenediamine with adipic acid directly or using stable derivatives such as the diacid chloride of adipic acid (ClOC-(CH₂)₄-COCl) in a condensation polymerization reaction.

Step 5: Relate the polymer to its applications. The polymer shown is nylon-6,6, which is widely used in climbing ropes and violin strings due to its high tensile strength and durability. Understanding the structure-property relationship is key to appreciating its utility.

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Key Concepts

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

Types of Polymers

Polymers can be classified into various types based on their chemical structure and the nature of their monomers. Common types include polyamides, which are formed from the reaction of amines and carboxylic acids, and polyesters, which are made from diols and dicarboxylic acids. Understanding these classifications is essential for identifying the type of polymer presented in the question.

Hydrolysis of Polymers

Hydrolysis is a chemical process that involves the breakdown of polymers into their monomeric units through the addition of water. In the context of the question, complete hydrolysis of the polyamide structure will yield the corresponding amine and carboxylic acid monomers. This concept is crucial for determining the monomers released during hydrolysis.

Monomer Structure and Derivatives

Monomers are the basic building blocks of polymers, and their structures dictate the properties of the resulting polymer. In addition to the original monomers, stable derivatives can also be used to synthesize polymers. Identifying these monomers and their derivatives is key to understanding how the polymers in the question can be synthesized and what alternatives exist for their production.

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Related Practice

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

Predict the products (if any) of the following acid–base reactions.

(a) acetic acid + ammonia

(b) phthalic acid + excess NaOH

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

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

(e) heptanoic acid

Textbook Question

(A true story.) Chemistry lab students added an excess of ethylmagnesium bromide to methyl furoate, expecting the Grignard reagent to add twice and form the tertiary alcohol. After water workup, they found that the product was a mixture of two compounds. One was the expected product having two ethyl groups, but the unexpected product had added three ethyl groups. Propose a mechanism to explain the formation of the unexpected product.

Textbook Question

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

(e)

Textbook Question

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

(g)

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