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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711당신이 사용하는 게 아니라요?교과서 변경
15장, 문제 85c

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.
c. Chemical reaction showing the conversion of toluene to an amide derivative with a carbonyl group.

검증된 단계별 안내
1
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.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
4m

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

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.
추천 영상:
04:20
Carboxylic Acids Nomenclature

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.
추천 영상:
08:19
Intro to Aromaticity

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.
추천 영상:
가이드 코스
1:16
Synthesis of Amino Acids: Strecker Synthesis Example 1