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

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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3:23 minutes

Problem 54b

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile

Verified step by step guidance

Step 1: Begin by identifying the functional group transformation required. In this case, you need to convert a carboxylic acid (-COOH) group in 3-ethylpentanoic acid to a nitrile (-CN) group in 3-ethylpentanenitrile.

Step 2: Recognize that carboxylic acids can be converted to nitriles through an intermediate step involving the formation of an amide. First, react 3-ethylpentanoic acid with ammonia (NH₃) to form 3-ethylpentanamide. This reaction typically requires heating and may use a dehydrating agent.

Step 3: Once the amide is formed, dehydrate the amide to form the nitrile. This can be accomplished using a dehydrating agent such as phosphorus pentoxide (P₂O₅) or thionyl chloride (SOCl₂). The dehydration reaction removes water and converts the amide (-CONH₂) to the nitrile (-CN).

Step 4: Ensure proper reaction conditions, such as temperature and solvent, to optimize the yield of 3-ethylpentanenitrile. For example, the dehydration step may require heating under reflux.

Step 5: Verify the product by analyzing its structure using techniques such as infrared spectroscopy (IR) to confirm the presence of the nitrile group (sharp peak around 2200 cm⁻¹) and ensure the conversion is complete.

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Key Concepts

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

Functional Groups

Understanding functional groups is essential in organic chemistry as they determine the chemical reactivity and properties of molecules. In this synthesis, we are converting a carboxylic acid (3-ethylpentanoic acid) into a nitrile (3-ethylpentanenitrile), which involves recognizing the functional groups involved and their transformations.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions are key mechanisms in organic synthesis where a nucleophile replaces a leaving group in a molecule. In this case, converting the carboxylic acid to a nitrile may involve a nucleophilic substitution step, where a suitable reagent can facilitate the transformation by replacing the -OH group of the acid.

Reagents and Reaction Conditions

Different reagents and reaction conditions are crucial for achieving specific transformations in organic synthesis. For the conversion of 3-ethylpentanoic acid to 3-ethylpentanenitrile, one might use reagents like thionyl chloride (SOCl2) to convert the acid to an acid chloride, followed by reaction with a nitrile source, highlighting the importance of selecting appropriate reagents.

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Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(b) Predict the products formed when phosgene reacts with 1 equivalent of methanol, followed by 1 equivalent of aniline.

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Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

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Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

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Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(d) ethyl acetate → 3-methylpentan-3-ol

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Determine the major product for the following reaction.

Multiple Choice

Determine the major product for the following reaction.

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Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile

Key Concepts

Functional Groups

Nucleophilic Substitution Reactions

Reagents and Reaction Conditions

Watch next

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(b) 3-ethylpentanoic acid → 3-ethylpentanenitrile