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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Problem 30b

Textbook Question

Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.
(b)

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Identify the products of the ozonolysis reaction: acetophenone (C₆H₅C(O)CH₃) and formaldehyde (HCHO).

Recognize that ozonolysis cleaves the double bond of an alkene to form carbonyl compounds. The products suggest the original alkene had a structure that splits into these two fragments.

Determine the structure of the alkene that would yield acetophenone and formaldehyde upon ozonolysis. The alkene must have a double bond between the carbon atoms that will form the carbonyl groups in the products.

Consider the connectivity of the alkene: the carbon atom that forms acetophenone must be connected to the phenyl group and a methyl group, while the carbon atom that forms formaldehyde must be connected to a hydrogen atom.

Propose the structure of the alkene: phenylpropene (C₆H₅CH=CH₂), where the double bond is between the terminal carbon and the adjacent carbon, allowing for the formation of acetophenone and formaldehyde upon ozonolysis.

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Key Concepts

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

Ozonolysis Reaction

Ozonolysis is a reaction where ozone (O3) cleaves alkenes to form carbonyl compounds, such as aldehydes and ketones. The reaction involves the formation of an ozonide intermediate, which is then reduced to yield the final products. This process is useful for determining the position of double bonds in alkenes and synthesizing specific carbonyl compounds.

Alkene Structure

The structure of the alkene is crucial in ozonolysis as it determines the resulting carbonyl compounds. In the given image, the alkene must have a double bond positioned such that upon cleavage, it forms the specified ketone and aldehyde. Understanding the connectivity and substitution pattern of the alkene helps predict the ozonolysis products accurately.

Reductive Workup

Reductive workup in ozonolysis involves using a reducing agent, such as dimethyl sulfide (CH3SCH3), to convert the ozonide intermediate into stable carbonyl compounds. This step is essential to prevent the formation of unwanted by-products and ensure the desired aldehydes and ketones are obtained. The choice of reducing agent can influence the yield and purity of the final products.

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Related Practice

Textbook Question

Predict the product of the following aldehyde/ketone syntheses.

(a)

Textbook Question

Ozonolysis of an unknown alkene A gives the products shown. Predict the product that results from hydrogenation of alkene A. [There are multiple answers, but only show the one with the 6-membered ring.]

Textbook Question

Suggest reagents to carry out the following transformation.

Textbook Question

Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with CH₃SCH₃

(b)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O (viii) 1. O₃ 2. CH₃SCH₃

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (viii) 1. O₃ 2. CH₃SCH₃

(f)

Textbook Question

Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with CH₃SCH₃

(c)

Textbook Question

What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage

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Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.(b)

Key Concepts

Ozonolysis Reaction

Alkene Structure

Reductive Workup

Watch next

Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.
(b)