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Aldehydes Ketones and Carboxylic Acids question

2004 · Shift 0 · Q16
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Aldehydes Ketones and Carboxylic Acids question

2004 · Shift 0 · Q16

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Which of the following undergoes reaction with 50% sodium hydroxide solution to give the corresponding alcohol and acid?
  1. A
    Phenol
  2. B
    Benzoic acid
  3. C
    Butanal
  4. D
    Benzaldehyde
View written solutionFree

Correct answer: D

  1. Identify the reaction being asked

    The reaction of a compound with concentrated alkali such as 50%50\%50% sodium hydroxide giving the corresponding alcohol and acid is the Cannizzaro reaction.

    General form: 2RCHO+conc. NaOH→RCH2OH+RCOONa2RCHO + \text{conc. NaOH} \rightarrow RCH_2OH + RCOONa2RCHO+conc. NaOH→RCH2​OH+RCOONa On acidification, the salt gives the corresponding acid.

  2. Condition for Cannizzaro reaction

    Cannizzaro reaction is shown by aldehydes that do not contain an α\alphaα-hydrogen.

  3. Check each option

    A: Phenol

    • Phenol is not an aldehyde.
    • It does not undergo Cannizzaro reaction.
    • Incorrect.

    B: Benzoic acid

    • Benzoic acid is already a carboxylic acid.
    • It will not give alcohol and acid with 50%50\%50% NaOH.
    • Incorrect.

    C: Butanal

    • Butanal is an aldehyde, but it has α\alphaα-hydrogen atoms.
    • Aldehydes with α\alphaα-hydrogen undergo aldol reaction in presence of base, not Cannizzaro reaction.
    • Incorrect.

    D: Benzaldehyde

    • Benzaldehyde is an aldehyde with no α\alphaα-hydrogen.
    • Therefore it undergoes Cannizzaro reaction with concentrated NaOH: 2C6H5CHO+NaOH→C6H5CH2OH+C6H5COONa2C_6H_5CHO + \text{NaOH} \rightarrow C_6H_5CH_2OH + C_6H_5COONa2C6​H5​CHO+NaOH→C6​H5​CH2​OH+C6​H5​COONa
    • On acidification, sodium benzoate gives benzoic acid.
    • So it gives the corresponding alcohol and acid.
    • Correct.
  4. Final answer

    The compound is benzaldehyde.

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