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Ch. 22 - Conjugated Systems 2: Pericyclic Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471당신이 사용하는 게 아니라요?교과서 변경
21장, 문제 41b

Predict the product of the Claisen reactions shown.
(b) Chemical structure of a Claisen rearrangement reaction with a chlorinated allyl vinyl ether and heat symbol.

검증된 단계별 안내
1
Step 1: Understand the Claisen condensation reaction. It involves the reaction between two esters or one ester and a ketone in the presence of a strong base, typically an alkoxide, to form a β-keto ester or a β-diketone.
Step 2: Identify the reactants in the given Claisen reaction. Look for the ester or ketone groups that will participate in the reaction.
Step 3: Determine the base used in the reaction. Common bases include sodium ethoxide (NaOEt) or sodium methoxide (NaOMe). The base deprotonates the α-hydrogen of the ester, forming an enolate ion.
Step 4: Predict the nucleophilic attack. The enolate ion formed will attack the carbonyl carbon of another ester molecule, leading to the formation of a new carbon-carbon bond.
Step 5: Consider the final product formation. After the nucleophilic attack, the intermediate undergoes protonation and elimination of the alkoxide ion, resulting in the formation of a β-keto ester or β-diketone as the final product.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.

주요 개념

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

Claisen Condensation

The Claisen condensation is a reaction where two esters or one ester and a ketone react in the presence of a strong base to form a β-keto ester or a β-diketone. This reaction involves the formation of a new carbon-carbon bond and is crucial for synthesizing complex molecules in organic chemistry.
추천 영상:
08:28
Claisen Condensation

Enolate Ion Formation

Enolate ions are formed when a strong base deprotonates the α-hydrogen of an ester or ketone, creating a resonance-stabilized anion. This enolate ion acts as a nucleophile in the Claisen condensation, attacking the carbonyl carbon of another ester, leading to the formation of the product.
추천 영상:
02:26
Formation of Enolates

Acid Workup

After the Claisen condensation, an acid workup is typically performed to neutralize the reaction mixture and protonate the alkoxide intermediate, resulting in the final β-keto ester or β-diketone product. This step is essential to stabilize the product and complete the reaction process.
추천 영상:
01:31
Oxidative Workup Mechanism: