Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 23, Problem 7Q
Interpretation Introduction

Interpretation:

The systematic name for the given steroid is to be determined.

Concept introduction:

Steroids are a group of compounds that are obtained from lipids of plants and animals. Chemically, they are the derivatives of perhydrocyclopentanophenanthrene ring system.

Pregnane is a 21-carbon saturated hydrocarbon steroid that is responsible for producing progestins. It is an alkane-based steroid, but group of 5α or β pregnan-ol are alcohol-based steroids.

Androstan are a group of steroid hormones. The 5αEstranone group of steroids include hormones, such as androgen, estrogen, and progesterone.

Organic Chemistry, Chapter 23, Problem 7Q

The numbering of the carbon atoms and naming of the ring system are done as shown in the figure. The A, B ring junction may be cis or trans, but B, C and C, D ring junctions are mostly trans.

The methyl groups attached at the points of the ring junction are called angular methyl groups and they are the reference points for the stereochemical designations.

Conventionally, groups that lie on the top of the molecule, same as that of the angular methyl group, are designated as βgroups while those at the bottom are designated as αgroups. When α and β positions are applied for hydrogen atom at C-5, and the A, B ring junction is cis, it is designated as 5βseries and when the A, B ring junction is trans, it is designated as 5αseries.

The nature of the Rgroup(s) at the carbon-position determines the base name of the individual steroid.

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