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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1:39 minutes

Problem 15b

Textbook Question

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

Verified step by step guidance

Identify the functional group in methyl acetate. Methyl acetate is an ester with the general structure \( RCOOR' \), where \( R \) is a methyl group and \( R' \) is also a methyl group.

Determine the target compound's functional group. Acetamide contains an amide functional group \( RCONH_2 \), where \( R \) is a methyl group.

Recognize the type of reaction needed to convert an ester to an amide. This transformation typically involves aminolysis, where the ester reacts with an amine or ammonia to replace the \( -OR' \) group with \( -NH_2 \).

Select the appropriate neutral nucleophile. In this case, ammonia (\( NH_3 \)) is a neutral nucleophile that can react with methyl acetate to form acetamide.

Outline the reaction mechanism. The nucleophilic attack by \( NH_3 \) on the carbonyl carbon of methyl acetate leads to the formation of a tetrahedral intermediate. This intermediate then eliminates methanol (\( CH_3OH \)) to yield acetamide.

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Key Concepts

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

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. They are typically negatively charged or neutral molecules with lone pairs of electrons. In organic synthesis, nucleophiles attack electrophilic centers, facilitating the formation of new bonds. Understanding the nature of nucleophiles is crucial for predicting reaction pathways and outcomes.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. This process can occur via two main mechanisms: SN1 and SN2. The choice of nucleophile and the structure of the substrate influence the reaction pathway. Recognizing these mechanisms is essential for determining how to synthesize specific compounds from given starting materials.

Amide Formation

Amide formation is a specific type of reaction where a carboxylic acid or its derivative reacts with an amine or ammonia to produce an amide. In the context of synthesizing acetamide from methyl acetate, a neutral nucleophile such as ammonia or an amine can be used. Understanding the reactivity of carboxylic acid derivatives is key to successfully carrying out this transformation.

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Textbook Question

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

g. excess benzylamine

h. 4-chlorophenol

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

Identify the major and minor products of the following reaction:

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:

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