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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5:35 minutes

Problem 53

Textbook Question

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

Verified step by step guidance

Step 1: Identify the target alkene structure. The given structure is a long-chain alkene with a double bond in the middle. Olefin metathesis can be used to assemble this structure by combining smaller alkene units.

Step 2: Break the target alkene into two smaller alkene fragments. For example, the target alkene can be divided into two smaller alkenes, each containing half of the carbon chain length and a terminal double bond.

Step 3: Select appropriate starting materials. Choose two smaller alkenes that can undergo olefin metathesis to form the desired product. For instance, two terminal alkenes such as 1-hexene and 1-hexene can be used.

Step 4: Perform the olefin metathesis reaction. Use a suitable catalyst, such as Grubbs' catalyst, to facilitate the reaction. The catalyst will break and reform the double bonds, creating the desired product.

Step 5: Purify the product. After the reaction, isolate and purify the target alkene using techniques such as distillation or chromatography to ensure the desired structure is obtained.

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Key Concepts

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

Olefin Metathesis

Olefin metathesis is a chemical reaction that involves the exchange of alkene fragments to form new alkenes. This reaction is facilitated by catalysts, typically transition metal complexes, which enable the breaking and forming of carbon-carbon double bonds. It is a powerful tool in organic synthesis, allowing for the construction of complex molecules from simpler ones.

Alkene Structure and Reactivity

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, which significantly influences their reactivity. The presence of this double bond makes alkenes more reactive than alkanes, allowing them to participate in various reactions, including addition and metathesis. Understanding the structure of alkenes is crucial for predicting their behavior in chemical reactions.

Catalysts in Organic Reactions

Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. In olefin metathesis, specific catalysts, such as Grubbs or Schrock catalysts, are employed to facilitate the reaction between alkenes. The choice of catalyst can significantly affect the efficiency and selectivity of the reaction, making it essential to understand their role in organic synthesis.

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Related Practice

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.

(a)

Textbook Question

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

(c)

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

Predict the major organic product of the following reaction.

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(g)

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.

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

Key Concepts

Olefin Metathesis

Alkene Structure and Reactivity

Catalysts in Organic Reactions

Watch next

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