418 CHAPTER 7 ADVANCED MICROSCALE ORGANIC LABORATORY E 7-36. In this In this exp

Question

418 CHAPTER 7 ADVANCED MICROSCALE ORGANIC LABORATORY E 7-36. In this In this experiment, the protons at both the ? and a' positions relative to the ton from the y position results in the oxonium ion are quite acidic. Removal of a pro below) of the actual product, cholesta-3,5-dien-3-ol formation (pathway a Discussion section). Removal of a proton from mation (pathway b below) of an isomeric p cause the reaction is conducted under equilibrium the a' position would result in the for. cholesta-2.4-dien-3-ol acetate. Be conditions, the product obtained must more stable of the two possibilities. Why is cholesta-24-dien. 3-ol acetate less stable than cholesta-3,5-dien-3-ol acetate? Cl CH Acylium ion Cholesta-4-ene-3-one H,C ?? Cholesta-2,4-dien-3-ol acetate Cholesta-3,5-dien-3-ol acetate

Explanation / Answer

This can be explain the concept of mesomeric effect and conjugation.

In cholesta-2,4-dien-3-ol acetate, the continuation of the conjugation is destroyed, while in the other cholesta-3,5-dien-3-olacetate , it is maintained. As we know , the more perfectly conjugation, the more resonating structures and hence more will be the stability.Thats why cholesta-2,4-dien-3-ol acetate is less stable than cholesta-3,5-dien-3-ol acetate.

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