- AThe synthesis requires four aldol condensations between methanol and ethanol.
- BThe synthesis requires two aldol condensations and two Cannizzaro reactions.
- CThe synthesis requires three aldol condensations and one Cannizzaro reaction.
- DAlpha hydrogens of ethanol and methanol are involved in this reaction.
View written solutionFree
Correct answer: C
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Identify the target compound
Erythritol has structure: and is often written as in condensed form sense of a four-carbon polyol framework.
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Relevant industrial/laboratory synthesis idea
Erythritol is obtained from formaldehyde (from methanol) and acetaldehyde (from ethanol) under basic conditions.
- Formaldehyde:
- Acetaldehyde:
Here:
- acetaldehyde has -hydrogen, so it can form an enolate and undergo aldol addition,
- formaldehyde has no -hydrogen, so it cannot form enolate; after carbon-chain construction, aldehyde groups without -H can undergo Cannizzaro reduction.
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How the carbon chain is built
Start with acetaldehyde as the enolizable aldehyde and add formaldehyde stepwise.
Each aldol addition with formaldehyde introduces one unit after protonation.
The sequence is:
First aldol: (3-hydroxypropanal)
Second aldol:
Third aldol: This product is pentaerythrose-like intermediate containing one aldehyde group.
Thus, 3 aldol condensations/additions are needed to attach three groups to the carbon adjacent to the original aldehyde carbon.
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Final conversion to erythritol-type polyol framework
The remaining aldehyde group is converted to alcohol through Cannizzaro reaction (self oxidation-reduction under strong base, since this aldehyde has no -hydrogen at that stage).
Hence, 1 Cannizzaro reaction is involved.
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Check the options
A. Four aldol condensations between methanol and ethanol.
❌ Incorrect. Methanol and ethanol themselves do not directly undergo aldol condensation; their oxidation products formaldehyde and acetaldehyde are involved. Also the count is not four.B. Two aldol condensations and two Cannizzaro reactions.
❌ Incorrect. Chain extension requires three aldol steps, not two.C. Three aldol condensations and one Cannizzaro reaction.
✅ Correct.D. Alpha hydrogens of ethanol and methanol are involved in this reaction.
❌ Incorrect. Formaldehyde (from methanol) has no -hydrogen. Only acetaldehyde-derived species provides the enolizable hydrogen in aldol steps. -
Final answer
The correct statement is:
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