- Aacetophenone benzaldehyde p-tolualdehyde p- nitrobenzaldehyde
- Bacetophenone p-tolualdehyde benzaldehyde p- nitrobenzaldehyde
- Cp- nitrobenzaldehyde benzaldehyde p-tolualdehyde acetophenone
- Dbenzaldehyde acetophenone p- nitrobenzaldehyde p-tolualdehyde
View written solutionFree
Correct answer: B
-
Principle for nucleophilic addition to carbonyl compounds
The reactivity of aldehydes and ketones towards nucleophilic addition depends mainly on:
- Electronic effect: Greater positive charge on the carbonyl carbon increases reactivity.
- Steric effect: Less hindrance around the carbonyl carbon increases reactivity.
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Aldehydes vs ketones
Aldehydes are generally more reactive than ketones because:
- They have only one alkyl/aryl group and one hydrogen, so less steric hindrance.
- Ketones have two carbon-containing groups, which reduce electrophilicity and increase steric hindrance.
Therefore,
-
Compare the aromatic aldehydes
We now compare:
- benzaldehyde
- -tolualdehyde
- -nitrobenzaldehyde
In aromatic aldehydes, substituents on the benzene ring affect the electrophilicity of the carbonyl carbon.
(i) -Tolualdehyde
The -methyl group is electron-donating due to its effect and hyperconjugation. It decreases the positive character on the carbonyl carbon, so it makes nucleophilic addition slower than in benzaldehyde.
Hence,
(ii) -Nitrobenzaldehyde
The -nitro group is strongly electron-withdrawing by both and effects. It increases the positive character on the carbonyl carbon, so it makes nucleophilic addition faster than in benzaldehyde.
Hence,
-
Overall order
Combining all comparisons:
-
Check options
- A: acetophenone benzaldehyde -tolualdehyde -nitrobenzaldehyde ❌
- B: acetophenone -tolualdehyde benzaldehyde -nitrobenzaldehyde ✅
- C: reverse order ❌
- D: incorrect placement of acetophenone and -tolualdehyde ❌
Therefore, the correct option is B.
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