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Arrange the following compounds in increasing order of their reactivity in nucleophilic additionreactions.(a) Ethanal, Propanal, Propanone, Butanone(b) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone

Question

Arrange the following compounds in increasing order of their reactivity in nucleophilic additionreactions.(a) Ethanal, Propanal, Propanone, Butanone(b) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone

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Solution

(a) The reactivity of carbonyl compounds in nucleophilic addition reactions is determined by the electron withdrawing or donating effects of the groups attached to the carbonyl carbon.

  1. Ethanal (CH3CHO): This has one alkyl group (CH3) and one hydrogen attached to the carbonyl carbon. The alkyl group is electron donating, which reduces the positive charge on the carbonyl carbon, making it less susceptible to nucleophilic attack.

  2. Propanal (CH3CH2CHO): This has two alkyl groups attached to the carbonyl carbon, which further reduces the positive charge on the carbonyl carbon, making it less reactive than ethanal.

  3. Propanone (CH3COCH3): This has two alkyl groups attached to the carbonyl carbon, similar to propanal. However, the symmetry of the molecule makes it less reactive than propanal.

  4. Butanone (CH3CH2COCH3): This has three alkyl groups attached to the carbonyl carbon, which further reduces the positive charge on the carbonyl carbon, making it the least reactive of the four.

So, the order of reactivity is: Butanone < Propanone < Propanal < Ethanal

(b) The reactivity of these compounds is determined by the electron withdrawing or donating effects of the groups attached to the benzene ring.

  1. Benzaldehyde (C6H5CHO): This has no additional groups attached to the benzene ring, so it is the least reactive.

  2. p-Tolualdehyde (C6H4CH3CHO): This has a methyl group (CH3) attached to the benzene ring, which is electron donating and increases the reactivity of the carbonyl group.

  3. Acetophenone (C6H5COCH3): This has a carbonyl group attached to the benzene ring, which is electron withdrawing and decreases the reactivity of the carbonyl group.

  4. p-Nitrobenzaldehyde (C6H4NO2CHO): This has a nitro group (NO2) attached to the benzene ring, which is a strong electron withdrawing group and makes the carbonyl group the most reactive.

So, the order of reactivity is: Benzaldehyde < Acetophenone < p-Tolualdehyde < p-Nitrobenzaldehyde

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