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

10. Addition Reactions

Hydrogenation

Organic Chemistry

10. Addition Reactions

Hydrogenation

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1:14 minutes

Problem 45k(x)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D₂ , Pd/C.
(k)

Verified step by step guidance

Identify the type of reaction: The reaction involves an alkene reacting with deuterium (D₂) in the presence of a palladium on carbon (Pd/C) catalyst. This is a catalytic hydrogenation reaction, where the double bond in the alkene is reduced to a single bond by the addition of deuterium atoms.

Understand the mechanism: In catalytic hydrogenation, the alkene π-bond interacts with the surface of the Pd/C catalyst, allowing the D₂ molecule to dissociate into two D atoms. These D atoms are then added to the carbon atoms of the double bond in a syn-addition manner (both deuterium atoms add to the same face of the alkene).

Determine the product: The double bond in the alkene is replaced by a single bond, and each carbon atom of the former double bond gains one deuterium atom. The stereochemistry of the product will depend on the starting alkene's structure (e.g., cis or trans).

Consider regioselectivity and stereoselectivity: Since this is a simple addition of deuterium, there is no regioselectivity to consider. However, the syn-addition nature of the reaction means that the stereochemistry of the product will reflect this (e.g., if the alkene is cyclic, the deuterium atoms will add to the same face of the ring).

Write the product structure: Replace the double bond in the alkene with a single bond, and add one deuterium atom to each carbon of the former double bond. Ensure the stereochemistry is consistent with syn-addition if applicable.

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Key Concepts

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

Alkene Hydrogenation

Alkene hydrogenation is a chemical reaction where hydrogen (H₂) is added across the double bond of an alkene, converting it into an alkane. This process typically requires a catalyst, such as palladium on carbon (Pd/C), which facilitates the reaction by providing a surface for the alkene and hydrogen to interact. The result is a saturated hydrocarbon, which is generally more stable than the original alkene.

Role of Catalysts

Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. In the context of alkene hydrogenation, palladium on carbon (Pd/C) serves as a catalyst that lowers the activation energy required for the reaction to occur. This allows the reaction to proceed more efficiently and at lower temperatures than would otherwise be necessary.

Stereochemistry of Hydrogenation

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. During hydrogenation of alkenes, the addition of hydrogen can lead to different stereoisomers, depending on the orientation of the hydrogen atoms added. In the case of symmetrical alkenes, the product is typically a single alkane, but for unsymmetrical alkenes, the stereochemistry can lead to the formation of cis and trans isomers, which are important in determining the properties of the resulting compound.

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Related Practice

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D₂, Pd/C.

(d)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C;

(h)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D₂, Pd/C.

(h)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C

(k)

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(e)

Textbook Question

The chiral catalyst (R)-BINAP(COD)RhOTf was used in a hydrogenation reaction as part of the synthesis of fragment C of indinavir. Using the same alkene, predict the product that would be obtained if (S)-BINAP(COD)RhOTf were used instead.

Textbook Question

On a per alkene basis, which would have the more negative heat of hydrogenation?

Textbook Question

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

(b) H₂ , Ni (partial hydrogenation)

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Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D2 , Pd/C. (k)

Key Concepts

Alkene Hydrogenation

Role of Catalysts

Stereochemistry of Hydrogenation

Watch next

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D₂ , Pd/C.
(k)