Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions.

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asked Dec 27, 2017 in Chemistry by sforrest072 (157,439 points) 60 409 933

Arrange the following compounds in increasing order of their reactivity in nucleophilic
addition reactions.
(i)Ethanal, Propanal, Propanone, Butanone.
(ii)Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.
Hint:Consider steric effect and electronic effect.

1 Answer

+1 vote
answered Dec 27, 2017 by mdsamim (213,225 points) 5 10 15
selected Dec 27, 2017 by sforrest072
 
Best answer

The +I effect of the alkyl group increases in the order: Ethanal < Propanal < Propanone < Butanone The electron density at the carbonyl carbon increases with the increase in the +I effect. As a result, the chances of attack by a nucleophile decrease. Hence, the increasing order of the reactivities of the given carbonyl compounds in nucleophilic addition reactions is:
Butanone < Propanone < Propanal < Ethanal

The +I effect is more in ketone than in aldehyde. Hence, acetophenone is the least reactive in nucleophilic addition reactions. Among aldehydes, the +I effect is the highest in ptolualdehyde because of the presence of the electron-donating −CH3 group and the lowest
in p-nitrobezaldehyde because of the presence of the electron-withdrawing −NO2 group.
Hence, the increasing order of the reactivities of the given compounds is: Acetophenone < p-tolualdehyde < Benzaldehyde < p-Nitrobenzaldehyde

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