18.31 Aldehydes that have no a hydrogen undergo an intermolecular oxidation-reduction called the Cannizzaro reaction when the are treated with concentrated base. An example is the following reaction of benzaldehyde: oboros H HỌ OH 2 H₂O + (a) When the reaction is carried out in D₂O, the benzyl alcohol that is isolated contains no deuterium bound to carbon. It is CH-CH₂OD. What does this suggest about the mechanism for the reaction? (b) When (CH₂)₂CHCHO and Ba(OH)₂/H₂O are heated in a sealed tube, the reaction produces only (CH₂)2CHCH₂OH and [(CH3)2CHCO₂]₂Ba. Provide an explanation for the formation of these products.

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**18.31** Aldehydes that have no α-hydrogen undergo an intermolecular oxidation-reduction called the Cannizzaro reaction when they are treated with concentrated base. An example is the following reaction of benzaldehyde:

[Diagram] The reaction involves the transformation of two molecules of benzaldehyde (C6H5CHO) via HO⁻/H2O to produce benzyl alcohol (C6H5CH2OH) and benzoate (C6H5COO⁻).

**(a)** When the reaction is carried out in D2O, the benzyl alcohol that is isolated contains no deuterium bound to carbon. It is C6H5CH2OD. What does this suggest about the mechanism for the reaction?

**(b)** When (CH3)2CHCHO and Ba(OH)2/H2O are heated in a sealed tube, the reaction produces only (CH3)2CHCH2OH and [(CH3)2CHCOO]2Ba. Provide an explanation for the formation of these products.
Transcribed Image Text:**18.31** Aldehydes that have no α-hydrogen undergo an intermolecular oxidation-reduction called the Cannizzaro reaction when they are treated with concentrated base. An example is the following reaction of benzaldehyde: [Diagram] The reaction involves the transformation of two molecules of benzaldehyde (C6H5CHO) via HO⁻/H2O to produce benzyl alcohol (C6H5CH2OH) and benzoate (C6H5COO⁻). **(a)** When the reaction is carried out in D2O, the benzyl alcohol that is isolated contains no deuterium bound to carbon. It is C6H5CH2OD. What does this suggest about the mechanism for the reaction? **(b)** When (CH3)2CHCHO and Ba(OH)2/H2O are heated in a sealed tube, the reaction produces only (CH3)2CHCH2OH and [(CH3)2CHCOO]2Ba. Provide an explanation for the formation of these products.
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