ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 29, Problem 38P
Interpretation Introduction

(a)

Interpretation: The skeletal structure of the anabolic steroid methenolone from the given description is to be drawn.

Concept introduction: Steroids are composed of tetracyclic lipids. They have structure containing three six membered ring and one five membered ring. Some of the steroids are biologically active.

Interpretation Introduction

(b)

Interpretation: The skeletal structure of the anabolic steroid methenolone from the given description about the configurations at the stereogenic centers is to be drawn.

Concept introduction: Steroids are composed of tetracyclic lipids. They have structure containing three six membered ring and one five membered ring. Some of the steroids are biologically active.

The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

Concept introduction: In the presence of base, the hydroxyl group loses its proton to form alkoxide. The alkoxide attacks on the carbonyl carbon of acyl chloride or acylic anhydride to leading to the formation of acyl group and removal of chloride. This process is known as acylation.

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(v) Identify every chiral center in cholesterol (below) with an asterisk. HO (vi) Draw an energy vs. dihedral angle diagram that represents all the conformations of butane starting from the anti-conformation. (vii) Draw both chair conformations for the compound shown below using the templates provided. Circle the chair conformation that is lowest in energy. Br (viii) Draw a chair conformation that meets the following criteria. Axial chlorine at C5 Equatorial methyl at C4 Bromine on C2 that is cis to the chlorine 6 2 5 3 4
What is the relationship between these structures? H3CH2C OH CH3 HỌC HỒ CH(CH3)2 (A) conformers (C) enantiomers HO CH(CH3)2 CH2CH3 H3C OH CH3 (B) diastereomers (D) identical
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