Textbook Question
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(c) but-2-enal → but-2-enoic acid
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13. Alcohols and Carbonyl Compounds
Oxidizing Agent
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What is the product of the reaction?
A
B
C
D
No reaction
Verified step by step guidance1
Identify the functional groups in the starting material. The starting material is a diol, specifically a 1,2-diol, with two hydroxyl (OH) groups on adjacent carbon atoms.
Recognize the reagent used in the reaction. Sodium dichromate (Na2Cr2O7) is a strong oxidizing agent typically used to oxidize alcohols.
Consider the typical reactions of 1,2-diols with strong oxidizing agents. Sodium dichromate can cleave 1,2-diols, leading to the formation of carbonyl compounds.
Analyze the structure of the diol. The diol in question is a vicinal diol, which can undergo oxidative cleavage to form two carbonyl groups.
Conclude that the reaction conditions are suitable for oxidative cleavage of the diol, but the specific structure of the diol may lead to no reaction if the diol is resistant to oxidation under these conditions.
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