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Ch. 21 - Carboxylic Acid Derivatives
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
21장, 문제 50b

Predict the products of the following reactions.
(b)

검증된 단계별 안내
1
Step 1: Identify the functional groups in the reactants. The starting compound contains an ester group (R-COOCH3), and the reagent is methylamine (CH3NH2), which is a primary amine.
Step 2: Recognize the type of reaction. This is a nucleophilic acyl substitution reaction, where the amine will act as a nucleophile and attack the carbonyl carbon of the ester.
Step 3: Describe the mechanism. The lone pair of electrons on the nitrogen atom of CH3NH2 will attack the electrophilic carbonyl carbon of the ester, forming a tetrahedral intermediate.
Step 4: Explain the elimination step. The intermediate will collapse, expelling the methoxy group (-OCH3) as a leaving group and forming an amide bond (R-CONHCH3).
Step 5: Predict the product. The final product will be an amide, specifically N-methylcyclohexanecarboxamide, where the ester group is replaced by the amide group.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
47s

주요 개념

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

Nucleophilic Addition Reactions

Nucleophilic addition reactions involve the attack of a nucleophile, such as an amine, on an electrophilic carbon atom, typically found in carbonyl groups. In this case, methylamine (CH3NH2) acts as the nucleophile, attacking the carbonyl carbon of the cyclic compound, leading to the formation of an intermediate that can further react to yield the final product.
추천 영상:
08:27
Nucleophilic Addition

Formation of Imine

When an amine reacts with a carbonyl compound, it can form an imine through a condensation reaction. This process involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. The heat applied in the reaction can facilitate this transformation, promoting the formation of the imine product from the initial adduct.
추천 영상:
06:23
Imine Mechanism

Reactivity of Carbonyl Compounds

Carbonyl compounds, such as ketones and aldehydes, are highly reactive due to the polarized carbon-oxygen double bond. The carbon atom is electrophilic, making it susceptible to nucleophilic attack. In this reaction, the presence of the methoxy group (OCH3) can influence the reactivity and stability of the carbonyl, affecting the overall reaction pathway and product formation.
추천 영상:
01:40
Defining meso compounds.