What is the Product of the Following Reaction?

How Can I Solve No. 31?

Solution: From the image, the substrate appears to be 2 equivalents of furfural (furan-2-carbaldehyde) treated with:

OH⁻ (base), added slowly

H₂O

This is a classic aldol reaction.

Step 1: Identify the type of reaction

Furfural has an aldehyde but no α-hydrogens (the carbon next to the CHO group is part of the aromatic furan ring).

Since it cannot form an enolate, it cannot undergo a self-aldol condensation.

Step 2: What happens under a strong base?

An aldehyde with no α-hydrogens undergoes the Cannizzaro reaction instead.

The Cannizzaro reaction disproportionates 2 molecules of the aldehyde:

2RCHO+OH−→RCH2OH+RCOO−

After the water workup, the products remain:

Furfuryl alcohol (reduction product)

Furoate (or furoic acid after acidification) (oxidation product)

Since the workup shown is only H₂O, the carboxylate salt is usually written as furoate.

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