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When the ester attacked the aluminum of DIBAl-H, why did the carbonyl oxygen attack preferentially over the alkoxy oxygen?
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21. Aldehydes and Ketones: Nucleophilic Addition
DIBAL
Scelta multipla
Predict the major, organic product for the following reaction.
A
B
C
D
Guida verificata passo dopo passo1
Identify the functional groups in the starting material. The compound is a carboxylic acid, characterized by the presence of a carbonyl group (C=O) and a hydroxyl group (OH) attached to the same carbon.
Recognize the reagent used in the reaction. Lithium aluminum hydride (LiAlH4) is a strong reducing agent commonly used to reduce carboxylic acids to primary alcohols.
Understand the mechanism of reduction. LiAlH4 donates hydride ions (H-) to the carbonyl carbon, breaking the C=O double bond and forming an alkoxide intermediate.
Consider the second step, which involves quenching with H+. This step protonates the alkoxide intermediate, converting it into an alcohol.
Predict the major product. The carboxylic acid group in the starting material is reduced to a primary alcohol, resulting in the formation of a benzyl alcohol derivative.
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