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

Alkyne Halogenation

Organic Chemistry

10. Addition Reactions

Alkyne Halogenation

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1:53 minutes

Problem 52b

Textbook Question

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

Verified step by step guidance

Step 1: Identify the type of metathesis reaction. In this case, the reaction involves a cyclic compound with two double bonds and a catalyst, which suggests a ring-closing metathesis (RCM) reaction.

Step 2: Analyze the structure of the cyclic compound. The molecule contains two double bonds and ester functional groups. These double bonds are positioned in a way that allows for the formation of a smaller ring upon reaction.

Step 3: Understand the role of the catalyst. The Schrock or Grubbs catalyst facilitates the breaking and reforming of carbon-carbon double bonds, enabling the formation of new rings or rearrangements.

Step 4: Predict the product. The reaction will likely result in the formation of a smaller cyclic compound with a single double bond, as the two double bonds in the starting material undergo metathesis to form a new bond.

Step 5: Consider stereochemistry and functional groups. The product will retain the ester groups and may exhibit cis/trans isomerism depending on the reaction conditions and the specific catalyst used.

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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 parts between two molecules, typically involving alkenes. In organic chemistry, this process is facilitated by catalysts such as the Schrock or Grubbs catalysts, which help to break and form double bonds, leading to the formation of new compounds. Understanding the mechanism of metathesis is crucial for predicting the products of the reaction.

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 the types of products formed, making them essential for successful metathesis in synthetic organic chemistry.

Cyclic Compounds in Metathesis

Cyclic compounds, such as the one depicted in the image, can participate in metathesis reactions, leading to the formation of new cyclic or acyclic products. The strain in cyclic compounds can affect the reaction pathway and the stability of the products. Recognizing how the structure of the starting material influences the outcome of the reaction is vital for predicting the products in metathesis.

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Related Practice

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (i) HBr; (ii) HCl; (iii) HBr, H₂O₂ (iv) H₂SO₄, H₂O (v) 1. Hg(OAc)_2, H₂O 2. NaBH₄ ; (vi) 1. BH₃ 2. H₂O₂, NaOH

(d)

Textbook Question

What stereoisomers are obtained when 2-butyne undergoes each of the following reaction sequences?

a. 1. H₂/Lindlar catalyst 2. Br₂/CH₂Cl₂

Textbook Question

Show what reagents would be needed to synthesize the pheromone of the omnivorous leafroller (OLR) using olefin metathesis to assemble the molecule at the double bond.

Textbook Question

Propose a mechanism for the triolefin process using a metal alkylidene as the catalyst.

Textbook Question

Protonation of which of the following alkenes would be faster?

Textbook Question

The synthesis of five-membered lactones (cyclic esters) has been accomplished using the electrophilic addition of I―Cl to an alkyne. Suggest a mechanism for this cyclization reaction. (Structure modification of Yao, T.; Larock, R.C. J. Org. Chem. 2005, 70, 1432–1437.)

Textbook Question

Draw the mechanism for the following reaction:

Textbook Question

When alkynes are treated with water and bromine a bromoketone is produced. Provide a plausible arrow-pushing mechanism that accounts for the formation of this product.

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

Key Concepts

Metathesis Reactions

Schrock and Grubbs Catalysts

Cyclic Compounds in Metathesis

Watch next

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