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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2:53 minutes

Problem 46m

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.
(m)

Verified step by step guidance

Step 1: Identify the type of reaction. The reaction involves hydrogen gas (H₂) and a platinum (Pt) catalyst, which indicates a catalytic hydrogenation reaction. This type of reaction typically reduces double bonds (alkenes) to single bonds (alkanes).

Step 2: Analyze the structure of the reactant. The reactant is a cyclohexene derivative with one double bond in the ring and a methyl group attached to the ring. The double bond is the site of reactivity in this reaction.

Step 3: Predict the intermediate. In catalytic hydrogenation, there are no long-lived intermediates. The double bond interacts with the catalyst surface, allowing hydrogen atoms to add across the double bond in a syn addition manner.

Step 4: Determine the major product. The double bond in the cyclohexene ring will be fully reduced to a single bond, resulting in a cyclohexane ring. The methyl group remains attached to the same position on the ring.

Step 5: Consider stereochemistry. Since the addition of hydrogen occurs on the same face of the double bond (syn addition), stereochemistry is not a concern here because the product is a saturated ring (cyclohexane), which does not have stereochemical centers.

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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 unsaturated compound, typically alkenes or alkynes, to convert them into saturated hydrocarbons. This process is often facilitated by a catalyst, such as platinum (Pt), palladium (Pd), or nickel (Ni). In the context of the provided reaction, hydrogenation will convert the double bond in the aromatic compound into a single bond, resulting in a saturated product.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving double bonds, such as hydrogenation, the stereochemistry of the product can be significant, as it may lead to different isomers. Understanding stereochemistry is crucial for predicting the major products and their configurations, especially when chiral centers are formed or affected during the reaction.

Reaction Mechanism

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. It outlines the sequence of elementary steps, including the formation of intermediates and transition states. In the case of hydrogenation, the mechanism involves the adsorption of hydrogen onto the catalyst surface, followed by the transfer of hydrogen atoms to the unsaturated compound, leading to the formation of the final saturated product. Understanding the mechanism helps in predicting the products and intermediates involved.

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Related Practice

Textbook Question

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

i. (Z)-2,3-dichloro-2-butene + H₂, Pd/C

Textbook Question

Which stereoisomer of 3,4-dimethyl-3-hexene forms (3S,4S)-3,4-dimethylhexane and (3R,4R)-3,4-dimethylhexane when it reacts with H₂, Pd/C?

Textbook Question

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

j. (E)-2,3-dichloro-2-butene + H₂, Pd/C

Textbook Question

Draw the products, including their configurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents:

b. H₂, Pd/C

Textbook Question

Give the expected major product for each reaction, including stereochemistry where applicable.

(c)

(d)

Textbook Question

Give the expected major product for each reaction, including stereochemistry where applicable.

(a) but-1-ene + H₂/Pt

(b) cis-but-2-ene + H₂/Ni

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.]

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Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate. (m)

Key Concepts

Hydrogenation

Stereochemistry

Reaction Mechanism

Watch next

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.
(m)