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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4:21 minutes

Problem 12f

Textbook Question

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
f.

Verified step by step guidance

Step 1: Analyze the target compound. The structure shows an ester functional group, specifically an ethyl ester, attached to a benzene ring substituted with two nitro groups and a methyl group.

Step 2: Identify the starting material, acetyl chloride (CH3COCl). Acetyl chloride is an acyl chloride, which is reactive and can undergo nucleophilic acyl substitution reactions to form esters.

Step 3: Determine the neutral nucleophile required to form the ester. To synthesize the target compound, the nucleophile must be a phenol derivative with the same substitution pattern as the benzene ring in the target compound: a methyl group and two nitro groups.

Step 4: Select the appropriate phenol derivative. The nucleophile should be 2-methyl-4,6-dinitrophenol, as it matches the substitution pattern of the benzene ring in the target compound.

Step 5: Outline the reaction mechanism. Acetyl chloride reacts with 2-methyl-4,6-dinitrophenol in the presence of a base (such as pyridine) to neutralize the HCl byproduct. This results in the formation of the ester bond, yielding the target compound.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of acetyl chloride, the nucleophile must be neutral and capable of attacking the carbonyl carbon, leading to the formation of a new bond. Understanding this mechanism is crucial for predicting the products of reactions involving acetyl chloride.

Acetyl Chloride Reactivity

Acetyl chloride is a reactive acyl chloride that can undergo nucleophilic acyl substitution due to the presence of the electron-withdrawing chlorine atom. This reactivity allows it to react with various nucleophiles, including alcohols and amines, to form esters and amides, respectively. Recognizing the reactivity of acetyl chloride helps in selecting appropriate nucleophiles for synthesizing desired compounds.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. In the compound shown, the presence of nitro groups indicates that the aromatic ring is activated for further substitution. Understanding EAS is essential for predicting how the aromatic system will react with nucleophiles, especially when considering the influence of substituents on the ring's reactivity.

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Related Practice

Textbook Question

Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:

Textbook Question

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

Textbook Question

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

Textbook Question

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

Textbook Question

Write a mechanism for each of the following reactions:

b. the aminolysis of phenyl formate, using methylamine.

Textbook Question

Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.

Textbook Question

Propose a mechanism for the reaction of acetic anhydride with water.

Textbook Question

We saw that acid anhydrides react with alcohols, water, and amines. In which of these reactions can the tetrahedral intermediate eliminate the carboxylate ion even if it does not lose a proton before the elimination step? Explain.

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Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds? f.

Key Concepts

Nucleophilic Substitution

Acetyl Chloride Reactivity

Electrophilic Aromatic Substitution

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Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
f.