- A

- B
- C

- D

View written solutionFree
Correct answer: C
- Identify the substrate and reagent
The given aldehyde is propanal:
It is treated with excess formaldehyde in alkali under reflux.
- Recall the reaction type
An aldehyde having at least one -hydrogen undergoes crossed aldol reaction with formaldehyde in base.
Since formaldehyde has no -hydrogen, it acts only as the electrophile. Propanal forms an enolate and adds to formaldehyde.
Repeated hydroxymethylation can occur at the -carbon as long as -hydrogens are available.
For propanal, the -carbon is the carbon next to : It has 2 -hydrogens.
So, with excess HCHO, both -hydrogens are replaced by groups:
- What happens under strongly basic conditions with excess formaldehyde?
Now the product still contains an aldehyde group, but it has no -hydrogen left at the carbon adjacent to the aldehyde carbonyl (that carbon is now bonded to , two groups, and ).
Such aldehydes undergo Cannizzaro reaction in presence of formaldehyde/alkali.
In crossed Cannizzaro with formaldehyde:
- formaldehyde is oxidized to formate,
- the other aldehyde is reduced to alcohol.
Thus,
- Final major product
Therefore the major product is: More clearly:
This is a triol formed by double hydroxymethylation followed by crossed Cannizzaro reduction.
- Option matching
- Option B is , which is just 1-propanol, so it is not correct.
- The correct structure is the triol .
Hence the correct option is C.
- Comparison with stored answer
Stored correct answer: C
My derived answer: C
So they agree.
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