Textbook Question
Many of the condensations we have studied are reversible. The reverse reactions are often given the prefix retro-, the Latin word meaning “backward.” Propose mechanisms to account for the following reactions.
(a)
25. Condensation Chemistry
Aldol Condensation
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What product can be isolated from the following aldol condensation reaction?
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Verified step by step guidance1
Identify the reactants: The starting material is a cyclopentanone, which is a five-membered cyclic ketone.
Recognize the reaction conditions: The presence of hydroxide ion (OH-) and heat indicates an aldol condensation reaction.
Understand the mechanism: In an aldol condensation, the enolate ion formed from the ketone attacks the carbonyl carbon of another ketone molecule, forming a β-hydroxy ketone.
Consider dehydration: Under the reaction conditions, the β-hydroxy ketone can undergo dehydration to form an α,β-unsaturated ketone.
Predict the product: The final product is likely to be an α,β-unsaturated ketone, where the double bond is conjugated with the carbonyl group, resulting from the loss of water from the β-hydroxy ketone.
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