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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4:11 minutes

Problem 48c

Textbook Question

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

Verified step by step guidance

Analyze the target molecule provided in the image. The structure contains an alkene functional group and branching, indicating that the synthesis involves forming a double bond and controlling regioselectivity.

Determine the starting material. Based on the structure, a suitable precursor could be an alkyl halide or alcohol that can undergo elimination to form the alkene.

Choose the elimination reaction type. For this synthesis, a strong base such as NaOH or KOH can be used to promote an E2 elimination reaction, which is ideal for forming alkenes with controlled stereochemistry and regioselectivity.

Consider the reaction conditions. To favor the formation of the more substituted alkene (Zaitsev product), use a strong base and heat. Alternatively, if the less substituted alkene is desired (Hofmann product), use a bulky base like t-BuOK.

Verify the stereochemistry and regioselectivity of the product. Ensure that the chosen reagents and conditions align with the desired alkene structure in the target molecule.

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Key Concepts

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

Imine Formation

Imine formation is a key reaction in organic chemistry where an aldehyde or ketone reacts with a primary amine to form an imine. This reaction involves the nucleophilic attack of the amine on the carbonyl carbon, followed by dehydration to eliminate water. Understanding this process is crucial for synthesizing compounds that contain imine functional groups.

Reagents for Aldehyde and Ketone Synthesis

The synthesis of aldehydes and ketones often involves specific reagents such as Grignard reagents, lithium aluminum hydride, or oxidation agents. Each reagent has distinct mechanisms and conditions under which they operate, making it essential to choose the appropriate one based on the desired product and starting materials. Familiarity with these reagents is vital for effective synthesis.

Nucleophilic Addition Reactions

Nucleophilic addition reactions are fundamental in organic chemistry, particularly involving carbonyl compounds like aldehydes and ketones. In these reactions, a nucleophile attacks the electrophilic carbon of the carbonyl group, leading to the formation of alcohols, imines, or other derivatives. Understanding the mechanisms and outcomes of these reactions is essential for predicting the products of synthetic pathways.

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Related Practice

Textbook Question

Predict the product of the following reaction sequences.

(b)

Textbook Question

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

(a)

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.