An explanation, with reference to the accepted mechanism of nucleophilic acyl substitution, for the evidence of a tetrahedral intermediate is to be stated. Concept introduction: The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilc acyl substitution reaction, a nucleophile takes the position of a leaving group.

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Chapter 22, Problem 22.82P

Interpretation Introduction

Interpretation: An explanation, with reference to the accepted mechanism of nucleophilic acyl substitution, for the evidence of a tetrahedral intermediate is to be stated.

Concept introduction: The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilc acyl substitution reaction, a nucleophile takes the position of a leaving group.

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Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous−OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophllic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.

Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophllic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.

Compelling evidence for the existence of a tetrahedral intermediate innucleophilic acyl substitution was obtained in a series of elegantexperiments carried out by Myron Bender in 1951. The key experimentwas the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3)labeled at the carbonyl oxygen with 18O. Bender did not allow thehydrolysis to go to completion, and then examined the presence of alabel in the recovered starting material. He found that some of therecovered ethyl benzoate no longer contained a label at the carbonyloxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedralintermediate.