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

Previous problemNext problem

2:55 minutes

Problem 37d

Textbook Question

Draw structures of the following derivatives.
(d) the ethylene acetal of hexan-3-one

Verified step by step guidance

Step 1: Understand the problem. The task is to draw the ethylene acetal derivative of hexan-3-one. Hexan-3-one is a ketone with the carbonyl group located on the third carbon of a six-carbon chain. An acetal is formed when a ketone reacts with an alcohol under acidic conditions, and in this case, ethylene glycol (HOCH2CH2OH) is the alcohol used.

Step 2: Identify the reaction mechanism. The formation of an acetal involves two steps: (1) the nucleophilic attack of the alcohol on the carbonyl carbon, and (2) the removal of water to form the acetal structure. Ethylene glycol will react with hexan-3-one to form a cyclic acetal.

Step 3: Draw the structure of hexan-3-one. Represent the six-carbon chain with the ketone group (C=O) on the third carbon. Ensure the remaining carbons are saturated with hydrogen atoms.

Step 4: Draw the ethylene glycol molecule. Ethylene glycol is a two-carbon diol (HOCH2CH2OH). It has hydroxyl groups (-OH) on both ends of the molecule.

Step 5: Combine hexan-3-one and ethylene glycol to form the cyclic acetal. The two hydroxyl groups of ethylene glycol will react with the carbonyl group of hexan-3-one, forming a five-membered ring structure. Replace the carbonyl oxygen with the cyclic acetal structure, ensuring proper connectivity and stereochemistry.

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Key Concepts

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

Acetals and Hemiacetals

Acetals are formed when an aldehyde or ketone reacts with an alcohol in the presence of an acid catalyst, resulting in a carbon atom bonded to two alkoxy groups and a hydrogen atom. Hemiacetals, on the other hand, contain one alkoxy group and one hydroxyl group. Understanding the formation and structure of acetals is crucial for drawing derivatives like the ethylene acetal.

Hexan-3-one Structure

Hexan-3-one is a ketone with the molecular formula C6H12O, characterized by a carbonyl group (C=O) located at the third carbon of a six-carbon chain. Recognizing the structure of hexan-3-one is essential for understanding how it will react to form its acetal derivative, as the position of the carbonyl group influences the overall structure of the acetal.

Ethylene Acetal Formation

The ethylene acetal of a ketone is formed by reacting the ketone with ethylene glycol, which provides two -O- groups. This reaction typically occurs under acidic conditions, leading to the substitution of the carbonyl oxygen with the ethylene glycol moiety. Familiarity with this process is necessary to accurately depict the structure of the ethylene acetal derivative of hexan-3-one.

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