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青州's Question
Chemistry
Posted 4 months ago

a. Compound J\mathbf{J} is the major product formed in the reaction of compounds H\mathbf{H} and I\mathbf{I} as shown below:
(i) Draw the chemical structure of product J\mathbf{J}.
[3 marks]
(ii) Draw and discuss in detail the reaction mechanism for the formation of compound J\mathbf{J} from starting materials H\mathbf{H} and I\mathbf{I}. What is the name of this type of reaction?
[15 marks]
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Answer from Sia
Posted 4 months ago
Solution
1
Predict the product J: Given the reaction conditions and the molecular formula of the product C11H12O3C_{11}H_{12}O_3, we can deduce that a Claisen condensation followed by an acid-catalyzed cyclization occurs
2
Draw the structure of J: Based on the Claisen condensation, the ethyl group from compound I will form a bond with the carbonyl carbon of compound H. After cyclization, the final product will have a six-membered ring attached to the benzene ring, forming a 3,4-dihydro-2H-chromen-2-one structure
3
Reaction mechanism: The mechanism involves the deprotonation of compound I by NaOEt to form an enolate, which then attacks the carbonyl carbon of compound H. After the condensation step, acid-catalyzed cyclization leads to the formation of the chromenone ring system
4
Name of the reaction: This reaction is a combination of a Claisen condensation and an acid-catalyzed cyclization, which can be referred to as a Claisen-Schmidt condensation followed by a cyclization to form the chromenone system
1 Answer
The chemical structure of product JJ is a 3,4-dihydro-2H-chromen-2-one derivative with the molecular formula C11H12O3C_{11}H_{12}O_3.
2 Answer
The reaction mechanism involves a Claisen condensation followed by an acid-catalyzed cyclization to form the chromenone ring system. The reaction is a combination of Claisen and Schmidt condensation followed by cyclization.
Key Concept
Claisen condensation and cyclization
Explanation
The reaction between compounds H and I under basic conditions leads to the formation of an enolate, which attacks the carbonyl carbon of another molecule to form a β-keto ester. Subsequent acid-catalyzed cyclization yields the chromenone ring system.

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