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

Previous problemNext problem

1:09 minutes

Problem 60b

Textbook Question

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(b)

Verified step by step guidance

Step 1: Understand the concept of retrosynthetic analysis. Retrosynthetic analysis involves breaking down a target molecule into simpler precursor molecules by working backward. This approach helps identify the starting materials and reagents needed for synthesis.

Step 2: Analyze the product (b) provided in the problem. Carefully examine its structure, functional groups, and stereochemistry to determine what type of reaction could produce it.

Step 3: Identify the reaction type that could lead to the formation of product (b). For example, if the product contains an alcohol group, it might have been formed via hydroboration-oxidation of an alkene. Alternatively, if the product contains a halogen, it might have been formed via halogenation of an alkene.

Step 4: Propose an alkene that could serve as the precursor to product (b). Ensure that the alkene does not undergo rearrangement during the reaction. Consider the regioselectivity and stereoselectivity of the reaction to match the structure of product (b).

Step 5: Suggest the reagent(s) required to convert the proposed alkene into product (b). For example, if the reaction involves hydroboration-oxidation, the reagents would be BH₃·THF followed by H₂O₂/NaOH. If halogenation is involved, the reagent might be Br₂ or Cl₂.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Retrosynthetic Analysis

Retrosynthetic analysis is a strategic approach in organic chemistry where chemists deconstruct a target molecule into simpler precursor structures. This method allows for the identification of potential synthetic routes by working backward from the desired product to simpler starting materials. It emphasizes the importance of understanding functional groups and reaction mechanisms to effectively plan a synthesis.

Alkenes

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond (C=C). They are key intermediates in organic synthesis due to their reactivity, which allows for various transformations, such as addition reactions. Understanding the properties and reactivity of alkenes is crucial for predicting the outcomes of reactions and selecting appropriate reagents in synthetic pathways.

Reagents in Organic Synthesis

Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. In organic synthesis, the choice of reagent can significantly influence the reaction pathway and the final product. Familiarity with common reagents and their mechanisms of action is essential for successfully proposing synthetic routes and ensuring that the desired products are obtained without unwanted rearrangements.

Watch next

Master General properties of catalytic hydrogenation. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

i. (Z)-3,4-dimethyl-3-heptene + H₂, Pd/C

Textbook Question

What stereoisomers would you expect to obtain from each of the following reactions?

Textbook Question

One of the principal components of lemongrass oil is limonene, C₁₀H₁₆. When limonene is treated with excess hydrogen and a platinum catalyst, the product is an alkane of formula C₁₀H₂₀. What can you conclude about the structure of limonene?

Textbook Question

A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active.

c. If this reaction could be accomplished using H₂ and a nickel catalyst, would the product be optically active? Explain.

Textbook Question

Draw the products of the following reactions, including their configurations:

Textbook Question

Show how you would accomplish the following transformations. You may use any additional reagents you need.

(d)

Multiple Choice

Provide the product of the following reaction.

Multiple Choice

Predict the major organic product of the following reaction.

Show more practices