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Aldehydes Ketones and Carboxylic Acids question

2020 · 3 Sep · Shift 2 · Q8
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Aldehydes Ketones and Carboxylic Acids question

2020 · 3 Sep · Shift 2 · Q8

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The increasing order of the reactivity of the following compound in nucleophilic addition reaction is : Propanal, Benzaldehyde, Propanone, Butanone
  1. A
    Butanone < Propanone < Benzaldehyde < Propanal
  2. B
    Benzaldehyde < Butanone < Propanone < Propanal
  3. C
    Propanal < Propanone < Butanone < Benzaldehyde
  4. D
    Benzaldehyde < Propanal < Propanone < Butanone
View written solutionFree

Correct answer: A

  1. Principle for nucleophilic addition to carbonyl compounds

    The reactivity of aldehydes and ketones toward nucleophilic addition depends mainly on:

    • Electronic effect: More positive carbonyl carbon means more reactive.
    • Steric hindrance: Less crowding around the carbonyl carbon means easier attack.
  2. General order: aldehydes vs ketones

    Aldehydes are generally more reactive than ketones because:

    • They have only one alkyl group (or one H), so there is less +I effect.
    • They are less sterically hindered.

    Hence, aldehydes>ketones\text{aldehydes} > \text{ketones}aldehydes>ketones

  3. Compare the two ketones: propanone vs butanone

    • Propanone: CH3COCH3CH_3COCH_3CH3​COCH3​
    • Butanone: CH3COC2H5CH_3COC_2H_5CH3​COC2​H5​

    The ethyl group in butanone has greater electron-donating effect and also causes more steric hindrance than a methyl group.

    Therefore, Butanone<Propanone\text{Butanone} < \text{Propanone}Butanone<Propanone

  4. Compare the two aldehydes: propanal vs benzaldehyde

    • Propanal: CH3CH2CHOCH_3CH_2CHOCH3​CH2​CHO
    • Benzaldehyde: C6H5CHOC_6H_5CHOC6​H5​CHO

    In benzaldehyde, the carbonyl group is conjugated with the benzene ring. Due to resonance, the positive character on the carbonyl carbon decreases, so nucleophilic addition becomes less favorable than in aliphatic aldehydes.

    Thus, Benzaldehyde<Propanal\text{Benzaldehyde} < \text{Propanal}Benzaldehyde<Propanal

  5. Combine all comparisons

    From above: Butanone<Propanone<Benzaldehyde<Propanal\text{Butanone} < \text{Propanone} < \text{Benzaldehyde} < \text{Propanal}Butanone<Propanone<Benzaldehyde<Propanal

  6. Match with options

    This matches Option A.


Final Answer: Butanone<Propanone<Benzaldehyde<Propanal\boxed{\text{Butanone} < \text{Propanone} < \text{Benzaldehyde} < \text{Propanal}}Butanone<Propanone<Benzaldehyde<Propanal​

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