In the following compounds, what is the increasing order of their reactivity towards nucleophilic addition reactions?
Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone
Answer & explanation
Correct answer: option 3
The correct answer is option 3. Acetophenone < p-Tolualdehyde < Benzaldehyde < p-Nitrobenzaldehyde.
To determine the increasing order of reactivity towards nucleophilic addition reactions for the given compounds (Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone), we need to consider the electronic effects of substituents on the carbonyl group and the nature of the carbonyl compound.
Analysis of Each Compound:
Benzaldehyde (\(C_6H_5CHO\)):
Electronic Effects: The phenyl group slightly stabilizes the carbonyl group through resonance but has a relatively neutral effect overall.
Reactivity: It has moderate reactivity towards nucleophilic addition.
p-Tolualdehyde (\(p-CH_3C_6H_4CHO\)):
Substituent Effect: The methyl group (\(CH_3\)) at the para position is an electron-donating group via the inductive effect and hyperconjugation.
Reactivity: The electron-donating effect of the methyl group reduces the electrophilicity of the carbonyl carbon, making it less reactive towards nucleophiles compared to benzaldehyde.
p-Nitrobenzaldehyde (\(p-NO_2C_6H_4CHO\)):
Substituent Effect: The nitro group (\(NO_2\)) at the para position is a strong electron-withdrawing group through both inductive and resonance effects.
Reactivity: The electron-withdrawing effect of the nitro group increases the electrophilicity of the carbonyl carbon, making it more reactive towards nucleophiles compared to benzaldehyde.
Acetophenone (\(C_6H_5COCH_3\)):
Nature of Carbonyl Group: As a ketone, the carbonyl carbon in acetophenone is less electrophilic compared to aldehydes because of the electron-donating effect of the alkyl group (\(CH_3\)).
Reactivity: Ketones are generally less reactive towards nucleophilic addition than aldehydes due to steric and electronic factors.
Increasing Order of Reactivity: Combining these considerations, the order of reactivity towards nucleophilic addition reactions is:
Acetophenone: Least reactive because it is a ketone and the carbonyl carbon is less electrophilic.
p-Tolualdehyde: Less reactive than benzaldehyde due to the electron-donating effect of the methyl group.
Benzaldehyde: More reactive than p-tolualdehyde and acetophenone.
p-Nitrobenzaldehyde: Most reactive due to the strong electron-withdrawing effect of the nitro group.
Therefore, the increasing order of their reactivity towards nucleophilic addition reactions is: 3. Acetophenone < p-Tolualdehyde < Benzaldehyde < p-Nitrobenzaldehyde