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

Nitrile to Ketone

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Nitrile to Ketone

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3:42 minutes

Problem 39c

Textbook Question

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.
(c) octan-1-ol → decan-2-one

Verified step by step guidance

Identify the target transformation: The goal is to convert octan-1-ol (an alcohol) into decan-2-one (a ketone). This involves chain elongation by two carbons and functional group transformation.

Convert octan-1-ol into a nitrile intermediate: First, oxidize octan-1-ol to octanal (an aldehyde) using an oxidizing agent like PCC (Pyridinium chlorochromate). Then, perform a nucleophilic addition of HCN (hydrogen cyanide) to the aldehyde to form octanenitrile.

Elongate the carbon chain of the nitrile: React octanenitrile with a Grignard reagent, such as ethylmagnesium bromide (CH₃CH₂MgBr). This step adds two carbons to the chain and forms an imine intermediate.

Hydrolyze the imine intermediate: Treat the imine with aqueous acid (H₃O⁺) to hydrolyze it into decan-2-one, completing the transformation.

Verify the product: Confirm that the final product is decan-2-one, a ketone with a 10-carbon chain and the carbonyl group on the second carbon.

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Key Concepts

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

Nitrile Chemistry

Nitriles are organic compounds containing a cyano group (-C≡N). They can be used as versatile intermediates in organic synthesis, allowing for the formation of various functional groups. In the context of the transformation from octan-1-ol to decan-2-one, nitriles can be formed through the reaction of alcohols with reagents like thionyl chloride or phosphorus pentachloride, followed by nucleophilic addition reactions.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In organic chemistry, nitriles can be reduced to primary amines or aldehydes using reducing agents such as lithium aluminum hydride (LiAlH4) or hydrogen gas in the presence of a catalyst. Understanding these reduction pathways is crucial for manipulating nitriles to achieve desired carbonyl compounds like decan-2-one.

Carbon Chain Lengthening

Carbon chain lengthening is a synthetic strategy used to increase the number of carbon atoms in a molecule. This can be achieved through various methods, including the use of nitriles as intermediates. In the transformation from octan-1-ol to decan-2-one, a key step may involve the formation of a longer-chain nitrile, followed by hydrolysis and subsequent reduction to yield the desired ketone, demonstrating the utility of nitriles in building complex organic structures.

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Related Practice

Textbook Question

Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.

(a) bromobenzene → propiophenone

(b) CH₃CH₂CN → heptan-3-one

Textbook Question

Show how you would add a Grignard reagent to an ester or a nitrile to synthesize

Textbook Question

A ketone can be prepared from the reaction of a nitrile with a Grignard reagent. Describe the intermediate formed in this reaction, and show how it can be converted to a ketone.

Textbook Question

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(b) cyclohexanecarboxamide → cyclohexyl ethyl ketone

Textbook Question

Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.

(f) CH₃(CH₂)₅CN

Textbook Question

Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.

(a) bromobenzene → propiophenone

(b) CH₃CH₂CN → heptan-3-one

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Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.(c) octan-1-ol → decan-2-one

Key Concepts

Nitrile Chemistry

Reduction Reactions

Carbon Chain Lengthening

Watch next

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.
(c) octan-1-ol → decan-2-one