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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2:45 minutes

Problem 52d

Textbook Question

Show how you would synthesize the following derivatives from appropriate carbonyl compounds.
(d)

Verified step by step guidance

Step 1: Identify the target molecule. The structure contains a benzene ring fused to a cyclohexane ring (tetralin structure) with a side chain containing an ether functional group (a methoxy group attached to a cyclopropane). This suggests the need for a carbonyl precursor and subsequent functional group transformations.

Step 2: Choose an appropriate carbonyl compound as the starting material. A ketone such as 1-tetralone (a ketone on the tetralin structure) can serve as the precursor for the synthesis. This is because ketones are versatile intermediates for introducing side chains via nucleophilic addition reactions.

Step 3: Perform a nucleophilic addition reaction to introduce the side chain. React the ketone with a Grignard reagent or organolithium reagent containing the desired side chain structure (e.g., a cyclopropylmethyl group). This step will form a tertiary alcohol intermediate.

Step 4: Convert the tertiary alcohol into the ether functional group. Use a methylating agent such as methyl iodide (CH3I) in the presence of a base (e.g., NaH or K2CO3) to replace the hydroxyl group with a methoxy group, forming the ether.

Step 5: Verify the stereochemistry and ensure the final product matches the target molecule. If necessary, use purification techniques such as recrystallization or chromatography to isolate the desired derivative.

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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 fundamental in organic chemistry and include aldehydes, ketones, carboxylic acids, and esters. Understanding their structure and reactivity is crucial for synthesizing derivatives, as they serve as key intermediates in various reactions.

Nucleophilic Addition Reactions

Nucleophilic addition reactions involve the attack of a nucleophile on the electrophilic carbon of a carbonyl group. This reaction is a cornerstone in organic synthesis, allowing for the formation of alcohols, amines, and other functional groups. Mastery of this concept is essential for designing synthetic pathways to create desired derivatives from carbonyl compounds.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another. In the context of synthesizing derivatives from carbonyl compounds, this concept encompasses various reactions such as reduction, oxidation, and substitution. Understanding these transformations is vital for manipulating carbonyl compounds to achieve specific target molecules.

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Related Practice

Textbook Question

A chemist failed to generate the alcohol using the reaction shown here.

(b) How could the reaction conditions be modified to allow formation of the product?

Textbook Question

Show how each of the following compounds could be prepared from the given starting material. Each requires a protecting group.

Textbook Question

Acetals can serve as protecting groups for 1,2-diols, as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called an acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.

Textbook Question

As discussed in Section 17.9.1, alkenes can be hydrogenated selectively in the presence of ketones. Suppose that was not the case, and suggest how you might use a protecting group strategy to generate A from B.

Textbook Question

What starting materials are required to synthesize the following compounds, using the Fischer indole synthesis?

Textbook Question

Show what amines and carbonyl compounds combine to give the following derivatives.

(d)

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Show how you would synthesize the following derivatives from appropriate carbonyl compounds.(d)

Key Concepts

Carbonyl Compounds

Nucleophilic Addition Reactions

Functional Group Transformations

Watch next

Show how you would synthesize the following derivatives from appropriate carbonyl compounds.
(d)