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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3:41 minutes

Problem 63b(i)

Textbook Question

Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways.
(b)

Verified step by step guidance

Identify the starting alkene: Begin by determining the alkene that, upon ozonolysis, will yield the desired carbonyl compound(s). Consider the structure of the target carbonyl(s) and work backwards to deduce the possible alkene precursor.

Draw the structure of the alkene: Once the starting alkene is identified, draw its structure. Ensure that the double bond is positioned such that its cleavage will lead to the formation of the desired carbonyl compounds.

Apply the ozonolysis reaction: Ozonolysis involves the reaction of the alkene with ozone (O3) followed by a reductive workup, typically using zinc (Zn) and acetic acid (CH3COOH) or dimethyl sulfide (DMS). Write the reaction equation showing the alkene reacting with ozone.

Predict the products: Upon completion of the ozonolysis reaction, the double bond in the alkene is cleaved, resulting in the formation of two carbonyl groups. Draw the structures of these carbonyl products.

Verify the synthesis: Check that the carbonyl products obtained from the ozonolysis match the target carbonyl(s) specified in the problem. Ensure that the synthesis pathway is logical and feasible.

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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 where ozone (O3) cleaves alkenes or alkynes to form carbonyl compounds such as aldehydes, ketones, or carboxylic acids. The reaction involves the formation of an ozonide intermediate, which is then reduced to yield the carbonyl products. Understanding the mechanism and the types of products formed is crucial for proposing a synthesis pathway using ozonolysis.

Carbonyl Compounds

Carbonyl compounds are organic molecules containing a carbon-oxygen double bond. They include aldehydes, ketones, carboxylic acids, and their derivatives. The reactivity of the carbonyl group, due to its polar nature, makes it a key functional group in organic synthesis. Recognizing the structure and reactivity of carbonyl compounds is essential for designing synthesis routes.

Synthesis Pathways

Synthesis pathways in organic chemistry involve a series of chemical reactions to construct a desired compound from simpler starting materials. This requires understanding the reactivity and compatibility of functional groups, as well as the conditions needed for each reaction step. Proposing a synthesis involves selecting appropriate reactions and intermediates to efficiently achieve the target molecule.

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Related Practice

Textbook Question

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

(h)

Textbook Question

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

(k)

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.

(e)

Textbook Question

Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways.

(a)

Textbook Question

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(b)

Textbook Question

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

(d)

Textbook Question

Predict the product of ozonolysis of the triglyceride shown.