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The oxygen in water is primarily (99.8%) 16O, but water enriched with the heavy isotopeO18is also available. When an aldehyde or ketone is dissolvedinO18-enriched water, the isotopic label becomes incorporated into thecarbonyl group. Explain.

R2C=O+H2OR2C=O+H2Owhere O =O18

Short Answer

Expert verified

Isotope labeling is a technique used in the 鈥渋nvestigation of rhe mechanism鈥 of the chemical reaction.

E.g.,Hydrolysis of ester, when carried out withlabeled oxygen (O18), results in the formation of alcohol with labeled oxygen atoms which concludes that the 鈥渃leavage of the alkyl - Oxygen鈥 bond has occurred.

Step by step solution

01

Step-by-Step SolutionStep 1: Isotope labeling

Isotope labeling is a technique used in the 鈥渋nvestigation of rhe mechanism鈥 of the chemical reaction.

E.g.,Hydrolysis of ester, when carried out withlabeled oxygen (O18), results in the formation of alcohol with labeled oxygen atoms which concludes that the 鈥渃leavage of the alkyl - Oxygen鈥 bond has occurred.

02

Step 2:Incorporation of Isotope labeling into a carbonyl group

The nucleophile addition reaction of the water on the ketone/aldehyde is shown as follows:

Labeled oxygen O18(represented by *)

Nucleophile addition reaction

The steps that involve nucleophile addition of water (neutral nucleophile) on the carbonyl carbon of aldehyde or ketone are all reversible.

As all the steps are reversible, the mechanism of nucleophile addition on the carbonyl carbon, the reverse mechanism, can be shown, responsible for incorporating labeled oxygen O18(represented by *) on the carbonyl carbon.

The reverse reaction of nucleophile addition of water in aldehyde/ketone is shown as follows:

Reverse nucleophile addition reaction

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