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

Ozonolysis

Organic Chemistry

10. Addition Reactions

Ozonolysis

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2:46 minutes

Problem 58d

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
d. O₃, −78 °C, followed by (CH₃)₂S

Verified step by step guidance

Step 1: Recognize the reaction type. The reaction involves ozonolysis, which is a process where ozone (O3) cleaves the double bond of an alkene, breaking it into two carbonyl compounds (aldehydes or ketones). The second reagent, (CH3)2S (dimethyl sulfide), is a reducing agent that prevents the formation of carboxylic acids or further oxidation.

Step 2: Identify the structure of the starting material. The given compound is 2-methyl-2-butene, which is a branched alkene with the structure: CH3-C(CH3)=CH-CH3. The double bond is between the second and third carbon atoms.

Step 3: Predict the cleavage of the double bond. During ozonolysis, the double bond is cleaved, and each carbon atom of the double bond is converted into a carbonyl group. This means the molecule will split into two fragments, each containing a carbonyl group.

Step 4: Assign the resulting fragments. After cleavage, the two fragments are: (1) a ketone (CH3-C=O) from the more substituted carbon of the double bond, and (2) an aldehyde (CH3-CH2-CHO) from the less substituted carbon of the double bond. The reducing agent (CH3)2S ensures that the aldehyde remains in its reduced form and does not oxidize further.

Step 5: Combine the information to determine the major products. The major products of this reaction are acetone (CH3-C=O-CH3) and propanal (CH3-CH2-CHO), which result from the cleavage of the double bond in 2-methyl-2-butene followed by reduction with (CH3)2S.

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Key Concepts

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

Ozonolysis

Ozonolysis is a reaction involving the cleavage of alkenes using ozone (O3) to form carbonyl compounds. In this process, the alkene reacts with ozone to form a molozonide, which rearranges to yield ozonides. These ozonides can then be reduced, typically with a reagent like dimethyl sulfide ((CH3)2S), to produce aldehydes or ketones, depending on the structure of the original alkene.

Reactivity of Alkenes

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, making them reactive due to the presence of π bonds. The reactivity of alkenes allows them to undergo various addition reactions, including electrophilic additions and ozonolysis. The structure and substitution pattern of the alkene influence the stability of intermediates and the final products formed during these reactions.

Product Determination

Determining the major product of a reaction involves analyzing the stability of potential products and the mechanism of the reaction. In ozonolysis, the major products are typically the most stable carbonyl compounds formed from the cleavage of the double bond. Understanding the regioselectivity and stereochemistry of the reaction is crucial for predicting the correct major product.

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Related Practice

Textbook Question

Professor Patrick Dussault (University of Nebraska at Lincoln) has developed an alternative to the standard two-step ozonolysis procedure requiring reduction of the ozonide in a second step. He uses 2 to 3 equivalents of pyridine, a mildly basic organic solvent, in a one-step process (Organic Letters, 2012, 14, 2242). Show the products you expect from the following examples.

(c)

(d)

Textbook Question

Predict the major products of the following reactions.

(c)

(d) 1-ethylcycloheptene + ozone, then (CH₃)₂S

Textbook Question

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

Textbook Question

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.

Textbook Question

What aspect of the structure of the alkene does ozonolysis not tell you?

Textbook Question

What reagents are needed to carry out the following syntheses?

Textbook Question

In contact with a platinum catalyst, an unknown alkene reacts with three equivalents of hydrogen gas to give 1-isopropyl-4-methylcyclohexane. When the unknown alkene is ozonized and reduced, the products are the following:

Deduce the structure of the unknown alkene.

Multiple Choice

Predict the products of the following reaction.

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