Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Problem 85c

Chapter 16, Problem 85c

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
c.

Verified step by step guidance

Step 1: Begin with the starting material, anisole (methoxybenzene). The first step involves introducing an acyl group onto the benzene ring via Friedel-Crafts acylation. Use an acyl chloride (e.g., ethanoyl chloride) and a Lewis acid catalyst such as AlCl₃ to form the ketone group on the benzene ring.

Step 2: After the acylation, the product will be 4-methoxyacetophenone. Next, convert the ketone group into an amide group. This can be achieved by reacting the ketone with an amine (e.g., ethylamine) in the presence of a reducing agent or activating agent such as NaBH₃CN or TiCl₄.

Step 3: Ensure the reaction conditions are controlled to favor the formation of the amide bond. This step involves nucleophilic attack by the amine on the carbonyl carbon of the ketone, followed by dehydration to form the amide.

Step 4: Verify the position of the substituents on the benzene ring. The methoxy group is an ortho/para-directing group, which ensures that the acylation occurs at the para position relative to the methoxy group.

Step 5: Purify the final product using techniques such as recrystallization or chromatography to isolate the desired compound, 4-methoxy-N-ethylbenzamide.

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Key Concepts

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

Carboxylation

Carboxylation is a chemical reaction that introduces a carboxyl group (-COOH) into a compound. This process is often achieved through the reaction of a carbonyl compound with carbon dioxide, typically in the presence of a catalyst. Understanding carboxylation is essential for synthesizing carboxylic acids from other organic compounds, as seen in the transformation of aromatic compounds in the provided reaction.

Aromatic Substitution Reactions

Aromatic substitution reactions involve the replacement of a hydrogen atom in an aromatic ring with another substituent. These reactions are crucial in organic chemistry as they allow for the functionalization of aromatic compounds. The mechanism often involves electrophilic aromatic substitution (EAS), where an electrophile attacks the electron-rich aromatic system, leading to the formation of new products while preserving the aromaticity of the ring.

Reagents in Organic Synthesis

Reagents in organic synthesis are substances used to bring about a chemical reaction. They can include acids, bases, oxidizing agents, reducing agents, and catalysts. Selecting the appropriate reagents is vital for achieving the desired transformation efficiently and selectively. In the context of the provided reaction, understanding which reagents facilitate carboxylation and aromatic substitution is key to successfully preparing the target compound.

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Related Practice

Textbook Question

The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols.

c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?

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Textbook Question

What product do you expect to obtain from each of the following reactions?

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Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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Textbook Question

The intermediate shown here is formed during the hydroxide-ion-promoted hydrolysis of the ester group. Propose a mechanism for the reaction.

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Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.c.

Verified video answer for a similar problem:

Key Concepts

Carboxylation

Aromatic Substitution Reactions

Reagents in Organic Synthesis

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
c.