Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
Question
Book Icon
Chapter 30, Problem 30.36P
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.

Blurred answer
Students have asked these similar questions
Image attached
Aspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.
(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

Chapter 30 Solutions

Organic Chemistry-Package(Custom)

Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning