Skip to main content
Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds문제 69i
22장, 문제 69i

Predict the products of the following reactions.
(i) Chemical reaction diagram showing reactants and conditions for a Michael addition reaction.

검증된 단계별 안내
1
Step 1: Identify the reaction type. This is a Claisen condensation reaction followed by hydrolysis and decarboxylation. The Claisen condensation involves the reaction of an ester with a ketone in the presence of a base to form a β-keto ester intermediate.
Step 2: Analyze the reactants. The first reactant is ethyl acetoacetate (CH₃COCH₂COOCH₂CH₃), which is an ester with an acidic α-hydrogen. The second reactant is cyclohexanone, a ketone with an α-hydrogen. The base used is sodium ethoxide (NaOCH₂CH₃), which will deprotonate the α-hydrogen of the ester to form an enolate ion.
Step 3: Mechanism of the Claisen condensation. The enolate ion formed from ethyl acetoacetate will attack the carbonyl carbon of cyclohexanone, leading to the formation of a new C-C bond. This results in a β-keto ester intermediate after the elimination of the ethoxide ion.
Step 4: Hydrolysis and decarboxylation. The β-keto ester intermediate undergoes hydrolysis in the presence of acid (H₃O⁺), converting the ester group into a carboxylic acid. Upon heating, the carboxylic acid undergoes decarboxylation, releasing CO₂ and forming the final product.
Step 5: Predict the product structure. The final product will be a substituted cyclohexanone with the new substituent derived from the ethyl acetoacetate reactant. The exact structure can be determined by tracing the connectivity formed during the Claisen condensation and subsequent steps.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
9m

주요 개념

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.
추천 영상:
02:16
Heck Reaction Mechanism

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity and the types of reactions that can occur. For example, alcohols, carboxylic acids, and amines each have distinct behaviors in chemical reactions.
추천 영상:
02:36
Identifying Functional Groups

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is essential for predicting the products of reactions, especially in cases where chirality or geometric isomerism is involved. Understanding stereochemistry helps in determining the specific isomers that may be produced in a reaction.
추천 영상:
가이드 코스
1:38
Polymer Stereochemistry Concept 1
관련 실천
교과서 질문

Predict the products of the following reactions.

(f)

915
views
교과서 질문

Show how you would accomplish the following conversions in good yields. You may use any necessary reagents.

(b)

690
views
교과서 질문

Predict the products of the following reactions.

(g)

840
views
교과서 질문

Predict the products of the following reactions.

(h)

895
views
교과서 질문

Show how you would accomplish the following conversions in good yields. You may use any necessary reagents.

(a)

567
views
교과서 질문

Predict the products of these reaction sequences.

2015
views