**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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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.

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.

Chemistry

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ISBN:9781305957404

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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

**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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