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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3:41 minutes

Problem 89b

Textbook Question

What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?
b.

Verified step by step guidance

Step 1: Identify the target compound's structure. The given compound contains a double bond, indicating it is likely synthesized via the Wittig reaction. The Wittig reaction involves a carbonyl compound and a phosphonium ylide to form an alkene.

Step 2: Analyze the structure of the target compound to determine the two fragments that would result from the cleavage of the double bond. The double bond divides the molecule into two parts: one derived from the carbonyl compound and the other from the phosphonium ylide.

Step 3: Determine the carbonyl compound. The fragment on the left side of the double bond (cyclopentyl group) corresponds to the carbonyl compound. This suggests that the carbonyl compound is cyclopentanone (C₅H₈O).

Step 4: Determine the phosphonium ylide. The fragment on the right side of the double bond (containing the isopropyl group and the ethyl group) corresponds to the phosphonium ylide. This suggests that the ylide is derived from (CH₃)₂CHCH₂PPh₃.

Step 5: Conclude the synthesis. The Wittig reaction between cyclopentanone and the phosphonium ylide (CH₃)₂CHCH₂PPh₃ will yield the target compound. Ensure the reaction conditions are appropriate for the Wittig reaction, typically involving a base like NaOH or NaH.

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Key Concepts

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

Carbonyl Compounds

Carbonyl compounds are organic molecules that contain a carbon atom double-bonded to an oxygen atom (C=O). They are classified into various types, including aldehydes, ketones, carboxylic acids, and esters. Understanding the reactivity of carbonyl compounds is crucial, as they participate in numerous organic reactions, including nucleophilic addition and condensation reactions, which are essential for synthesizing complex molecules.

Phosphonium Ylides

Phosphonium ylides are reactive intermediates formed by the deprotonation of phosphonium salts, characterized by a positively charged phosphorus atom and a negatively charged carbon atom. They are commonly used in the Wittig reaction, which allows for the synthesis of alkenes from carbonyl compounds. The choice of phosphonium ylide is critical, as it determines the structure of the alkene produced in the reaction.

Imine and Enamine Formation

Imine and enamine formation involves the reaction of carbonyl compounds with amines. An imine is formed when a carbonyl compound reacts with a primary amine, while an enamine is produced from a secondary amine. These reactions are significant in organic synthesis, as they provide pathways to create more complex structures and can serve as intermediates in various synthetic routes, including the synthesis of the compounds depicted in the question.

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Related Practice

Textbook Question

Give the nitrile and organometallic reagent you would use to make the following ketones. There are two possible answers for both.

(b)

Textbook Question

Draw a mechanism for the acidic hydrolysis of the magnesium salt shown below to acetophenone.

Textbook Question

What is the best set of reagents to use for the synthesis?

Textbook Question

What is the best set of reagents to use for the synthesis?

Textbook Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(a)

Textbook Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(d)

Textbook Question

Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.

(b)

Textbook Question

Show how Wittig reactions might be used to synthesize the following compounds. In each case, start with an alkyl halide and a ketone or an aldehyde.

(a) Ph–CH=C(CH₃)₂

(b) Ph–C(CH₃)=CH₂

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What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?b.

Key Concepts

Carbonyl Compounds

Phosphonium Ylides

Imine and Enamine Formation

Watch next

What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?
b.