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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3:24 minutes

Problem 45d(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.
(d)

Verified step by step guidance

Step 1: Recognize the type of reaction occurring. The reaction involves an alkene reacting with deuterium gas (D₂) in the presence of a palladium catalyst (Pd/C). 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.

Step 2: Understand the mechanism of the reaction. The palladium catalyst adsorbs the D₂ molecules onto its surface, breaking the D-D bond and forming activated deuterium atoms. These atoms are then transferred to the alkene, reducing the double bond.

Step 3: Identify the structure of the starting alkene. Determine the position of the double bond in the alkene and consider the stereochemistry of the molecule, as the addition of deuterium is typically syn (both deuterium atoms add to the same face of the double bond).

Step 4: Predict the product. Replace the double bond in the alkene with single bonds to deuterium atoms. Ensure that the stereochemistry of the product reflects the syn addition of deuterium.

Step 5: Verify the product. Check that the resulting molecule is fully saturated (no double bonds remain) and that the deuterium atoms are correctly added to the original positions of the double bond.

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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 (Pd), to facilitate the reaction. The addition of hydrogen occurs in a syn fashion, meaning that both hydrogen atoms add to the same side of the double bond, resulting in a saturated product.

Deuterium (D₂) as a Reagent

Deuterium (D₂) is an isotope of hydrogen that contains one neutron, making it heavier than regular hydrogen. When used in hydrogenation reactions, deuterium replaces hydrogen atoms in the product, resulting in deuterated compounds. This is significant in organic chemistry for tracing reactions and studying mechanisms, as the presence of deuterium can affect the physical and chemical properties of the resulting molecules.

Catalytic Conditions (Pd/C)

Palladium on carbon (Pd/C) is a widely used catalyst in organic reactions, particularly in hydrogenation. The palladium provides active sites for the adsorption of both the alkene and hydrogen, facilitating the reaction. The carbon support enhances the surface area and stability of the palladium, making the catalyst effective for promoting the addition of hydrogen or deuterium to alkenes under mild conditions.

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Related Practice

Textbook Question

What product results when the following molecules are treated with H₂ Pd/C? Be sure to indicate the relative stereochemical outcome. Draw both enantiomers of any racemic mixtures. [It is difficult to control the stoichiometry of gases so there is enough H₂ to reduce all alkenes.]

(b)

Textbook Question

Because deuterium behaves like hydrogen in chemical reactions yet is detected differently, chemists use the incorporation of deuterium to better understand the subtleties of reaction mechanisms. Deuterium is incorporated by replacing H₂ with D₂ in the hydrogenation reaction. Identify the product expected when the alkenes in Assessment 9.34 react with D₂ and Pd/C. [Don't worry about showing all diastereomers.]

Textbook Question

A misguided chemist attempted to synthesize trans-1,2-dimethylcyclohexane via the hydrogenation of 1,2-dimethylcyclohexene. Explain why this is not possible.

Textbook Question

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

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

(k)

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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.(d)

Key Concepts

Alkene Hydrogenation

Deuterium (D₂) as a Reagent

Catalytic Conditions (Pd/C)

Watch next

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