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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5:27 minutes

Problem 79

Textbook Question

Identify the major and minor products of the following reaction:

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Step 1: Analyze the reactants. The molecule contains two nucleophilic functional groups: a primary amine (-NH2) and a secondary amine (-NH). Both can react with the electrophilic acetyl chloride (CH3COCl). The hydroxyl group (-OH) is less nucleophilic and unlikely to react under these conditions.

Step 2: Consider the reaction conditions. Since only 1 equivalent of acetyl chloride is provided, only one nucleophilic site will react. The primary amine (-NH2) is more nucleophilic than the secondary amine (-NH) due to less steric hindrance and higher electron density.

Step 3: Predict the major product. The primary amine will likely react with acetyl chloride to form an amide bond. The reaction mechanism involves nucleophilic attack by the amine on the carbonyl carbon of acetyl chloride, followed by the elimination of HCl.

Step 4: Predict the minor product. If the secondary amine reacts instead, it will form a different amide product. However, this is less likely due to steric hindrance and the lower nucleophilicity of the secondary amine compared to the primary amine.

Step 5: Summarize the outcome. The major product will be the amide formed from the reaction of the primary amine with acetyl chloride. The minor product, if formed, would result from the reaction of the secondary amine with acetyl chloride.

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Key Concepts

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

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks a carbonyl carbon, leading to the replacement of a leaving group. This reaction is characteristic of carboxylic acid derivatives, such as esters, amides, and acyl chlorides. Understanding this mechanism is crucial for predicting the major and minor products formed during the reaction.

Carboxylic Acid Derivatives

Carboxylic acid derivatives include compounds like acyl chlorides, esters, and amides, which can undergo nucleophilic acyl substitution. Each derivative has different reactivity due to the nature of the leaving group and the electrophilicity of the carbonyl carbon. Recognizing the type of derivative involved in the reaction helps in determining the expected products.

Product Distribution

In reactions involving nucleophilic acyl substitution, the distribution of products can be classified as major and minor based on factors such as sterics, electronics, and the stability of the resulting compounds. Major products are typically more stable or formed in greater quantities, while minor products may arise from less favorable pathways. Analyzing these factors is essential for predicting the outcome of the reaction.

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Related Practice

Textbook Question

What acyl chloride and amine are required to synthesize the following amides?

a. N-ethylbutanamide

b. N,N-dimethylbenzamide

Textbook Question

Write the mechanism for each of the following reactions:

b. the reaction of benzoyl chloride with excess methylamine to form N-methylbenzamide

Textbook Question

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

a. sodium acetate

b. water

Textbook Question

Starting with methyl acetate, what neutral nucleophile would you use to synthesize each of the following compounds? b. acetamide

Textbook Question

a. When a carboxylic acid is dissolved in isotopically labeled water (H₂O₁₈) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.

Textbook Question

An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product is formed? Explain.

Textbook Question

a. Identify the two products obtained from the following reaction:

Textbook Question

What reagent should be used to carry out the following reaction?

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