Textbook Question
What two sets of reagents (each consisting of a carbonyl compound and phosphonium ylide) can be used for the synthesis of the following alkene?
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21. Aldehydes and Ketones: Nucleophilic Addition
Wittig Reaction
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Predict the major, organic product for the following reaction.
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Verified step by step guidance1
Identify the reaction type: The presence of Ph₃P indicates a Wittig reaction, which is used to convert aldehydes or ketones into alkenes.
Analyze the reactants: The starting material is an aldehyde with a cyclopentanone group. The Wittig reagent is a phosphonium ylide, which will react with the aldehyde.
Understand the mechanism: The Wittig reaction involves the formation of a betaine intermediate, followed by the formation of an oxaphosphetane, which then decomposes to form the alkene product.
Predict the product: The major product of a Wittig reaction is typically an alkene formed by replacing the carbonyl group with a double bond between the carbon of the aldehyde and the carbon of the ylide.
Consider stereochemistry: Wittig reactions can lead to E/Z isomers, but in this case, the product is achiral, indicating no stereocenters are formed in the major product.
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