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

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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2:19 minutes

Problem 37c

Textbook Question

Draw structures of the following derivatives.
(c) cyclopropanone oxime

Verified step by step guidance

Understand the problem: Cyclopropanone oxime is a derivative of cyclopropanone, where the oxime functional group (-C=NOH) is attached to the carbonyl carbon of cyclopropanone. The goal is to draw the correct structure of this compound.

Start with the base structure: Draw the cyclopropanone molecule. Cyclopropanone consists of a three-membered cyclopropane ring with a carbonyl group (C=O) attached to one of the carbons in the ring.

Replace the carbonyl oxygen: In the oxime derivative, the oxygen atom of the carbonyl group is replaced by a double-bonded nitrogen atom with a hydroxyl group (-OH) attached to it. This forms the oxime functional group (-C=NOH).

Attach the oxime group: Modify the cyclopropanone structure by replacing the carbonyl oxygen with the oxime group. Ensure that the nitrogen is double-bonded to the carbon and the hydroxyl group is attached to the nitrogen.

Verify the structure: Check that the resulting structure has a three-membered cyclopropane ring with the oxime group (-C=NOH) correctly attached to the carbon that originally had the carbonyl group. Ensure all atoms have the correct number of bonds and the structure adheres to valency rules.

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Key Concepts

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

Cyclopropanone Structure

Cyclopropanone is a three-membered cyclic ketone with the formula C3H6O. Its structure consists of a cyclopropane ring with a carbonyl group (C=O) attached to one of the carbon atoms. Understanding the geometry and reactivity of cyclopropanone is essential for drawing its derivatives, as the ring strain influences its chemical behavior.

Oxime Formation

Oximes are compounds formed by the reaction of aldehydes or ketones with hydroxylamine (NH2OH). This reaction replaces the carbonyl oxygen with a hydroxyl group (–OH) and introduces a nitrogen atom, resulting in a C=N bond. Recognizing how to convert cyclopropanone into cyclopropanone oxime is crucial for accurately depicting its structure.

Stereochemistry of Cyclopropanone Oxime

Stereochemistry refers to the spatial arrangement of atoms in molecules and can significantly affect their properties. Cyclopropanone oxime can exist in two geometric isomers due to the C=N bond, which can be either E (trans) or Z (cis). Understanding these isomers is important for accurately representing the oxime structure and predicting its reactivity.

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