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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Problem 45e(ix,x)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C; and (x) D₂ , Pd/C.
(e)

Verified step by step guidance

Step 1: Analyze the given alkene structure. The molecule contains a double bond, which is the reactive site for the hydrogenation reactions. The double bond is located between two carbon atoms in the chain.

Step 2: Understand the reaction conditions. (ix) H₂, Pd/C is a catalytic hydrogenation reaction where molecular hydrogen (H₂) adds across the double bond in the presence of a palladium catalyst. This results in the conversion of the alkene to an alkane by adding one hydrogen atom to each carbon of the double bond.

Step 3: Predict the product for (ix). The double bond will be completely reduced, and the two carbons involved in the double bond will each gain a single hydrogen atom. The rest of the molecule remains unchanged.

Step 4: Understand the reaction conditions for (x). D₂, Pd/C is similar to the previous reaction, but instead of hydrogen (H₂), deuterium gas (D₂) is used. Deuterium is an isotope of hydrogen, so the double bond will be reduced, and each carbon of the double bond will gain a single deuterium atom instead of hydrogen.

Step 5: Predict the product for (x). The double bond will be completely reduced, and the two carbons involved in the double bond will each gain a single deuterium atom. The rest of the molecule remains unchanged. The final product will be a fully saturated alkane with deuterium atoms at the positions of the original double bond.

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Key Concepts

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

Hydrogenation

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H₂) to an alkene or alkyne, converting it into an alkane. This reaction typically requires a catalyst, such as palladium on carbon (Pd/C), which facilitates the breaking of the double or triple bonds. The result is a saturated hydrocarbon, which is generally more stable and less reactive than its unsaturated counterparts.

Deuteration

Deuteration is similar to hydrogenation but involves the addition of deuterium (D₂), an isotope of hydrogen, to an alkene or alkyne. This process also requires a catalyst like Pd/C and results in the formation of a deuterated alkane. Deuteration is often used in research to trace molecular pathways or to study reaction mechanisms due to the unique properties of deuterium compared to regular hydrogen.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving alkenes, the addition of hydrogen or deuterium can lead to different stereoisomers, depending on the orientation of the reactants and the reaction conditions. Understanding stereochemistry is crucial for predicting the specific products formed during hydrogenation or deuteration, especially in cases where chiral centers are involved.

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Related Practice

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)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C; and (x) D₂, Pd/C.

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br₂ (ii) Cl₂

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C; and (x) D₂, Pd/C.

(f)

Textbook Question

a. What stereoisomers are formed in the following reaction? Are they enantiomers or diastereomers?

b. Which stereoisomer is formed in greater yield?

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Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H2, Pd/C; and (x) D2 , Pd/C.(e)

Key Concepts

Hydrogenation

Deuteration

Stereochemistry

Watch next

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C; and (x) D₂ , Pd/C.
(e)