The structure of compound X in the given reactionis to be determined. Concept Introduction: Cyclic esters are called lactones and are often prepared by the intra-molecular cyclization of hydroxy substituted carboxylic acids. Electrophilic addition to the double bond of unsaturated carboxylic acids gives lactone. The phenylselenolactonization, the electrophilic reagent used is benzeneselenylchloride. Anti addition takes place in this cyclization. A selenoxide is produced by the oxidation of the C 6 H 5 Se substituent. It undergoes elimination to produce a double bond in the lactone by the elimination of the beta hydrogen which is away from the lactone oxygen.

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Chapter 19, Problem 37DSP

Interpretation Introduction

Interpretation:

The structure of compound X in the given reactionis to be determined.

Concept Introduction:

Cyclic esters are called lactones and are often prepared by the intra-molecular cyclization of hydroxy substituted carboxylic acids.

Electrophilic addition to the double bond of unsaturated carboxylic acids gives lactone.

The phenylselenolactonization, the electrophilic reagent used is benzeneselenylchloride.

Anti addition takes place in this cyclization.

A selenoxide is produced by the oxidation of the C6H5Se substituent. It undergoes elimination to produce a double bond in the lactone by the elimination of the beta hydrogen which is away from the lactone oxygen.

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