Aldehyde + Alcohol Acetal
| Aldehyde | Alcohol | ||
|---|---|---|---|
| HCHO | tBuOH | ||
| CH3CHO | MeOH |
The best combination is
- Aand
- BHCHO and MeOH
- Cand
- DHCHO and tBuOH
View written solutionFree
Correct answer: B
- Reaction involved: formation of acetal
An aldehyde reacts with an alcohol in the presence of acid to form first a hemiacetal and then an acetal:
This reaction is favored when:
- the aldehyde is more reactive,
- the alcohol is less hindered,
- acetal formation is not sterically difficult.
- Compare the aldehydes
The two aldehydes are:
- (formaldehyde)
- (acetaldehyde)
Formaldehyde is more reactive than acetaldehyde toward nucleophilic addition because it has:
- less steric hindrance,
- no electron-donating alkyl group.
So, for acetal formation:
- Compare the alcohols
The two alcohols are:
- (methanol)
- (tert-butanol)
Methanol is much better for acetal formation because:
- it is less hindered,
- it attacks the carbonyl carbon more easily.
Tert-butanol is highly hindered and under acidic conditions may also undergo side reactions/dehydration, so it is a poor choice for forming acetals.
Thus:
- Evaluate the options
Option A: and
Possible, but acetaldehyde is less reactive than formaldehyde.
Option B: and
This is the best combination because:
- is the most reactive aldehyde,
- is the least hindered alcohol.
Option C: and
Both components are less favorable; especially is very poor for acetal formation.
Option D: and
Formaldehyde is good, but is highly hindered, so this is inferior to option B.
- Conclusion
The best aldehyde–alcohol pair for acetal formation is:
So the correct option is B.
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