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

11. Radical Reactions

Radical Stability

Organic Chemistry

11. Radical Reactions

Radical Stability

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Problem 35

Textbook Question

The following polyunsaturated fat, which does not exist in nature, is oxidized at a rate similar to oleic acid (Table 11.14), despite having two cis-alkenes. Why?

Verified step by step guidance

Examine the structure of the polyunsaturated fat provided in the image. It contains two cis-alkene groups, which are double bonds with both hydrogen atoms on the same side of the double bond.

Understand that the oxidation rate of fatty acids is influenced by the presence and position of double bonds. Cis-alkenes can affect the molecular geometry and packing of the fatty acid chains.

Consider the role of double bonds in the oxidation process. Double bonds are sites of reactivity, and their presence can increase the susceptibility of the molecule to oxidation.

Compare the structure to oleic acid, which is a monounsaturated fatty acid with one cis double bond. Despite having two cis-alkenes, the polyunsaturated fat may have a similar oxidation rate due to similar structural features that affect reactivity.

Recognize that the overall molecular structure, including the length of the carbon chain and the position of double bonds, can lead to similar oxidation rates between the polyunsaturated fat and oleic acid, despite differences in the number of double bonds.

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Key Concepts

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

Polyunsaturated Fats

Polyunsaturated fats contain multiple double bonds in their carbon chain. These double bonds can be in cis or trans configurations, affecting the fat's physical properties and reactivity. The presence of multiple double bonds generally increases susceptibility to oxidation, which is a key factor in determining the stability and shelf life of fats.

Oxidation of Fatty Acids

Oxidation of fatty acids involves the reaction of oxygen with the double bonds in the fatty acid structure, leading to the formation of peroxides and other degradation products. The rate of oxidation can be influenced by the number and configuration of double bonds, as well as the presence of antioxidants. Understanding the oxidation process is crucial for evaluating the stability of different fatty acids.

Cis vs. Trans Configuration

The cis configuration of double bonds in fatty acids results in a bent structure, which affects how closely the molecules can pack together. This packing influences the melting point and physical properties of the fat. In contrast, trans configurations allow for a straighter chain, which can lead to increased stability and a higher melting point, impacting the oxidation rate and overall behavior of the fat.

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Related Practice

Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(a)

Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(b)

Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(c)

Textbook Question

Why is a 2° carbon radical more stable than a 1° carbon radical?

Textbook Question

Ethers can be converted into radicals, some more easily than others. Which of the following radicals is more stable, and thus, more likely to form?

Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(d)

Textbook Question

Methyl t-butyl ether (MTBE) is used preferentially over diethyl ether because it is less prone to form peroxides. Explain this observation in terms of the two structures.

Textbook Question

a. Which of the hydrogens in the structure in the margin is the easiest for a chlorine radical to remove?

b. How many secondary hydrogens does the structure have?

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