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

9. Alkenes and Alkynes

Hydrogenation of Alkynes

Organic Chemistry

9. Alkenes and Alkynes

Hydrogenation of Alkynes

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Problem 59a

Textbook Question

Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).

(a) H₂ , Pd

Verified step by step guidance

Step 1: Analyze the structure of linoleate triglyceride. It consists of a glycerol backbone esterified with three fatty acid chains, each containing two double bonds in the cis configuration.

Step 2: Understand the reaction conditions. The presence of H₂ and Pd indicates a catalytic hydrogenation reaction, which typically reduces double bonds in unsaturated compounds to single bonds.

Step 3: Predict the effect of hydrogenation on the fatty acid chains. The double bonds in the linoleate triglyceride will be converted to single bonds, resulting in saturated fatty acid chains.

Step 4: Note that the glycerol backbone and ester linkages remain unaffected during hydrogenation, as the reaction specifically targets the double bonds in the fatty acid chains.

Step 5: The final product will be a triglyceride with fully saturated fatty acid chains, as all double bonds are reduced to single bonds under these conditions.

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Key Concepts

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

Triglycerides

Triglycerides are esters formed from glycerol and three fatty acids. They are the main constituents of body fat in humans and animals, as well as vegetable fat. In the case of linoleic acid, which is a polyunsaturated fatty acid, the triglyceride will contain multiple double bonds, influencing its reactivity and the products formed during chemical reactions.

Hydrogenation

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H₂) to unsaturated bonds, typically double bonds in alkenes or alkynes. In the presence of a catalyst like palladium (Pd), hydrogenation converts unsaturated fatty acids into saturated ones, which can alter the physical properties of the triglyceride, such as melting point and stability.

Linoleic Acid

Linoleic acid is an essential polyunsaturated fatty acid with two double bonds, classified as an omega-6 fatty acid. It plays a crucial role in human health and is a key component of cell membranes. Understanding its structure and reactivity is vital for predicting the outcome of reactions, such as hydrogenation, which can lead to the formation of different fatty acid derivatives.

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Related Practice

Textbook Question

Predict the product of the following hydrogenation reactions.

(c)

Textbook Question

The following deprotonation step occurs during the trans reduction of an alkyne. Calculate K_eq for this reaction.

Textbook Question

Sodium amide, the base we use to deprotonate terminal alkynes, is synthesized by reducing ammonia via a mechanism similar to the reduction of alkynes in Figure 10.21. Suggest a mechanism for this reaction.

Textbook Question

Reduction of an alkyne using the Lindlar catalyst, a reaction presented in Section 10.6.2, produces only the cis-alkene. Why?

Textbook Question

Hydrogenation of which alkynes would produce the following cis-alkenes?

(b)

Textbook Question

Long, polarized bonds are also reducible in the same way that the C―C π bond of an alkyne is. Show a mechanism by which a C―Br bond might be reduced by sodium metal.

Textbook Question

What is the major product of the reaction of 1 mol of propyne with each of the following reagents?

g. excess H₂, Pd/C

h. H₂/Lindlar catalyst

Textbook Question

Describe the alkyne you should start with and the reagents you should use if you want to synthesize

c. trans-2-pentene.

d. 1-hexene.

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Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).(a) H2 , Pd

Key Concepts

Triglycerides

Hydrogenation

Linoleic Acid

Watch next

Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).

(a) H₂ , Pd