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Q.

Which of the following on treatment with 50% aqueous sodium hydroxide yields the corresponding alcohol and acid?

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a

C6H5CH2CHO

b

CH3COCH3

c

CH3CH2CH2CHO

d

C6H5CHO

answer is C.

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Detailed Solution

  • Benzaldehyde  (C6H5CHO) on treatment with 50% aq. NaOH yields Benzyl alcohol and sodium salt of benzoic acid as it does not contains an alpha hydrogen atom.
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  • The reaction is called cannizzaro reaction.
  • On the other hand, CH3CH2CH2CHO, CH3COCH3 and C6H5CH2CHO contain alpha hydrogen atom.
  • Hence, they undergo aldol condensation under similar conditions to form alpha beta-unsaturated carbonyl compounds.
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