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

Addition Reaction

Organic Chemistry

10. Addition Reactions

Addition Reaction

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5:34 minutes

Problem 52a

Textbook Question

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(a)

Verified step by step guidance

Step 1: Identify the type of reaction. This is a metathesis reaction, which involves the exchange of alkene fragments between molecules, facilitated by a catalyst such as the Schrock or Grubbs catalyst.

Step 2: Analyze the structure of the starting material. The molecule contains two alkenes: one within the aromatic ring system fused with oxygen (benzopyran structure) and another in the side chain.

Step 3: Determine the role of the catalyst. The Grubbs or Schrock catalyst will break the double bonds in the alkenes and form new double bonds by exchanging alkene fragments.

Step 4: Predict the products. The reaction will likely result in the formation of a cyclic product due to the proximity of the two alkenes in the molecule. The catalyst facilitates the formation of a new C=C bond, leading to ring closure.

Step 5: Consider stereochemistry and regioselectivity. The metathesis reaction typically forms the most thermodynamically stable product, which in this case would be a cyclic compound with a new double bond. Ensure the product structure reflects the correct connectivity and stability.

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Key Concepts

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

Metathesis Reactions

Metathesis reactions involve the exchange of partners between two alkenes, resulting in the formation of new alkenes. This process is facilitated by catalysts, such as the Schrock or Grubbs catalysts, which stabilize the transition state and lower the activation energy. Understanding the mechanism of metathesis is crucial for predicting the products formed from specific reactants.

Schrock and Grubbs Catalysts

Schrock and Grubbs catalysts are types of transition metal complexes used to promote metathesis reactions. Schrock catalysts are typically based on tungsten or molybdenum, while Grubbs catalysts are based on ruthenium. Each catalyst has unique properties that influence the reaction conditions and product distribution, making it important to choose the appropriate catalyst for specific substrates.

Product Prediction in Organic Reactions

Predicting the products of organic reactions, such as metathesis, requires an understanding of the structure and reactivity of the starting materials. In metathesis, the orientation and substitution patterns of the alkenes play a significant role in determining the final products. Analyzing the molecular structure and applying the principles of reaction mechanisms are essential for accurate product prediction.

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Related Practice

Textbook Question

Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to

(a) meso-2,7-dimethyloctane-4,5-diol, (CH₃)₂CHCH₂CH(OH)CH(OH)CH₂CH(CH₃)₂.

Textbook Question

Predict the products formed when CH₃CH₂–C≡C:^–Na⁺ reacts with the following compounds.

a. ethyl bromide

b. tert-butyl bromide

c. formaldehyde

Textbook Question

Show how you would accomplish the following synthetic conversions.

c. 1-methylcyclopentanol → 2-chloro-1-methylcyclopentanol

Problem-Solving Hint: The opening of a halonium ion is driven by its electrophilic nature. The weak nucleophile attacks the carbon bearing more positive charge.

Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(h)

Textbook Question

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.

(c)

Textbook Question

Show how you might use olefin metathesis to assemble the following alkenes from smaller units:

(a)

(b)

Textbook Question

Starting with ethyne, describe how the following compounds can be synthesized:

a. (3S,4R)-4-bromo-3-hexanol and (3R,4S)-4-bromo-3-hexanol

Multiple Choice