ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 31, Problem 31.15P
Interpretation Introduction

Interpretation: The enantiomer and any two diastereomers of cholesterol are to be drawn, and the position for OH group of cholesterol as an axial or equatorial is to be identified.

Concept introduction: Steroids, a group of tetracyclic lipids composed of one five-membered ring and three six-membered rings. Thesse rings are lettered by A, B, C, and D. Most of the steroids contain two angular methyl groups. These methyl groups are numbered as C18 and C19 respectively.

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Draw the structure of ,-diethyl--propylthiopentane.  With explanation
A. Provide a stepwise mechanism for the formation of nerolidyl pyrophosphate fromfarnesylpyrophosphate B. Provide a stepwise mechanism for the formation of carbocation 1 from nerolidylpyrophosphate. Number the backbone carbons of nerolidyl pyrophosphate from 1 to 11 as shown, andinclude the carbon numbering in your structure of 1 C. Following from B, give an arrow-pushing mechanism to convert 1 to 2 and 2 to 3. Use thebackbone carbon numbering from 1 to indicate where carbon atoms ended up in 2 and 3 D. In addition to forming epi-cedrol, carbocation 3 gives three minor byproducts: a diastereomericalcohol and two alkenes. Draw mechanisms that could give rise to these three products
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ORGANIC CHEMISTRY

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