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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3:14 minutes

Problem 37b

Textbook Question

Draw structures of the following derivatives.
(b) the semicarbazone of cyclobutanone

Verified step by step guidance

Understand the problem: A semicarbazone is a derivative formed by the reaction of a ketone or aldehyde with semicarbazide. Cyclobutanone is a cyclic ketone with a four-membered ring. The goal is to draw the structure of the semicarbazone derivative of cyclobutanone.

Recall the reaction mechanism: Semicarbazide (NH2-NH-C(=O)-NH2) reacts with the carbonyl group (C=O) of the ketone. The reaction involves nucleophilic attack by the -NH2 group of semicarbazide on the carbonyl carbon, followed by the elimination of water (H2O).

Draw the structure of cyclobutanone: Cyclobutanone consists of a four-membered ring with a ketone group (C=O) attached to one of the carbons in the ring.

Combine the structures: Replace the oxygen atom of the carbonyl group in cyclobutanone with the semicarbazone group (-NH-N=C). The resulting structure will have the semicarbazone group attached to the four-membered ring.

Verify the structure: Ensure that the semicarbazone derivative has the correct connectivity, with the semicarbazone group (-NH-N=C) properly bonded to the carbon that was originally part of the carbonyl group in cyclobutanone.

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Key Concepts

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

Semicarbazone Formation

Semicarbazones are formed by the reaction of carbonyl compounds, such as ketones and aldehydes, with semicarbazide. This reaction involves nucleophilic addition where the nitrogen of the semicarbazide attacks the carbonyl carbon, followed by dehydration to form a double bond between the carbon and nitrogen. Understanding this process is crucial for drawing the correct structure of the semicarbazone derivative.

Cyclobutanone Structure

Cyclobutanone is a cyclic ketone with a four-membered ring structure containing a carbonyl group (C=O). Its unique ring strain and geometry influence its reactivity and the types of derivatives it can form. Recognizing the structure of cyclobutanone is essential for accurately depicting its semicarbazone derivative.

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another during chemical reactions. In the case of semicarbazone formation, the carbonyl group of cyclobutanone is converted into an imine-like structure. This concept is important for understanding how different functional groups can be manipulated to create new compounds in organic synthesis.

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