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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3:32 minutes

Problem 37g

Textbook Question

Draw structures of the following derivatives.
(g) the (E) isomer of the ethyl imine of propiophenone

Verified step by step guidance

Understand the problem: You are tasked with drawing the (E) isomer of the ethyl imine derivative of propiophenone. This involves forming an imine functional group and ensuring the (E) configuration is achieved.

Recall the structure of propiophenone: Propiophenone is an aromatic ketone with the structure C₆H₅-CO-CH₂-CH₃. The ketone group (-CO-) is the reactive site for imine formation.

Understand imine formation: An imine is formed by the reaction of a ketone or aldehyde with a primary amine. In this case, ethylamine (CH₃-CH₂-NH₂) reacts with the ketone group of propiophenone, replacing the oxygen atom with a -N=CH-CH₂-CH₃ group.

Determine the (E) configuration: The (E) isomer refers to the trans configuration of the imine double bond. This means the substituents on either side of the C=N bond must be on opposite sides. For the imine of propiophenone, the phenyl group (C₆H₅) and the ethyl group (CH₂-CH₃) should be on opposite sides of the C=N bond.

Draw the structure: Start with the phenyl group (C₆H₅) attached to the carbon of the C=N bond. On the other side of the C=N bond, place the ethyl group (CH₂-CH₃) trans to the phenyl group. Complete the structure by attaching the ethylamine-derived nitrogen atom to the C=N bond and ensuring all valencies are satisfied.

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Key Concepts

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

E/Z Isomerism

E/Z isomerism is a type of stereoisomerism that occurs in alkenes and other compounds with restricted rotation around a double bond. The 'E' (from the German 'entgegen') designation indicates that the highest priority substituents on either side of the double bond are on opposite sides, while 'Z' (from 'zusammen') indicates they are on the same side. Understanding this concept is crucial for accurately drawing the correct isomer of a compound.

Imine Formation

Imine formation is a reaction between a carbonyl compound (like an aldehyde or ketone) and an amine, resulting in the creation of an imine. This process involves the nucleophilic attack of the amine on the carbonyl carbon, followed by dehydration to eliminate water. Recognizing how imines are formed helps in understanding the structure of the ethyl imine derived from propiophenone.

Propiophenone Structure

Propiophenone is an aromatic ketone with the structure C6H5C(O)C2H5, where a phenyl group is attached to a carbonyl group, which is further connected to an ethyl group. This structure is essential for understanding the derivatives formed from it, including the ethyl imine. Familiarity with the parent compound's structure aids in visualizing and drawing its derivatives accurately.

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